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This document contains 14 multiple choice questions from a chapter about antiulcer agents. The questions cover topics like the receptors involved in gastric acid secretion, the structure and properties of histamine, and the development of H2 receptor antagonists like cimetidine. Chain extension was used to develop guanidine-containing compounds as the distance between the binding group and imidazole ring impacts whether the molecule binds as an agonist or antagonist. Chelation binding theory was proposed to explain interactions between guanidines and carboxylates in receptor binding sites.
This document contains 14 multiple choice questions from a chapter about antiulcer agents. The questions cover topics like the receptors involved in gastric acid secretion, the structure and properties of histamine, and the development of H2 receptor antagonists like cimetidine. Chain extension was used to develop guanidine-containing compounds as the distance between the binding group and imidazole ring impacts whether the molecule binds as an agonist or antagonist. Chelation binding theory was proposed to explain interactions between guanidines and carboxylates in receptor binding sites.
This document contains 14 multiple choice questions from a chapter about antiulcer agents. The questions cover topics like the receptors involved in gastric acid secretion, the structure and properties of histamine, and the development of H2 receptor antagonists like cimetidine. Chain extension was used to develop guanidine-containing compounds as the distance between the binding group and imidazole ring impacts whether the molecule binds as an agonist or antagonist. Chelation binding theory was proposed to explain interactions between guanidines and carboxylates in receptor binding sites.
Patrick: An Introduction to Medicinal Chemistry 3e
Chapter 22: Antiulcer agents
Type: multiple choice question Title: Chapter 22 Question 01 01) Which o the ollo!in" a"ents does not aect the release o "astric acid rom parietal cells# Feedback: Acetylcholine$ "astrin and histamine %ind to their respecti&e receptors on parietal cells to induce the release o "astric acid' (oradrenaline does not do this' Page reference: )*2+)*3 a' Acetylcholine ,%' (oradrenaline c' -astrin d' .istamine Type: matching question Title: Chapter 22 + Question 02 02) /he structure o histamine is sho!n %elo!' What la%els are used to distin"uish the nitro"ens at positions A$ 0 and C# Feedback: /he +nitro"en is the one at the end o the side chain on histamine' /he nitro"en is the one in the imida1ole rin" closest to the side chain' /he nitro"en is the imida1ole nitro"en urthest a!ay rom the side chain' Page reference: )** a' A 2 %' 0 2 c' C 2 Type: multiple choice question Title: Chapter 22 Question 03 03) What sort o heterocyclic rin" is present in histamine# Feedback: /he rin" systems "i&en are as ollo!s Page reference: )** a' Imida1olidine %' Pyridine c' Pyrrole ,d' Imida1ole Type: multiple choice question Title: Chapter 22 Question 0* 0*) What type o histamine receptor is associated !ith the dilation o %lood &essels# Feedback: /here are t!o main types o histamine receptor$ .1 and .2' .3 and .* receptors do not e3ist' /he .1 receptor is tar"eted %y traditional antihistamines !hile the .2 receptor is tar"eted %y histamine anta"onists used in anti+ulcer therapy' Page reference: )**+)*4 ,a' .1 %' .2 c' .3 d' .* Type: multiple choice question OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Title: Chapter 22 Question 04 04) Which ailment is not treated %y con&entional histamine anta"onists actin" on the .1 receptor# Feedback: Anti+ulcer a"ents actin" as histamine anta"onists tar"et .2+receptors on parietal cells' Page reference: )**+)*4 a' .ay e&er %' Insect %ites ,c' 7lcers d' Asthma Type: multiple choice question Title: Chapter 22 Question 0) 0)) /here are t!o possi%le tautomers or histamine' /automer A is more sta%le than tautomer 0' Why# Feedback: /he side chain is electron !ithdra!in" due to the positi&ely char"ed ammonium "roup at the end o the chain' 8ince this is an inducti&e eect$ it is elt more at the nitro"en than the nitro"en since the ormer is nearer the side chain' Inducti&e eects decrease !ith the num%er o %onds in&ol&ed' /his means that the nitro"en is "oin" to %e less %asic and less likely to use its lone pair o electrons to orm a %ond to hydro"en' Page reference: )42+)43 ,a' /he side chain has an inducti&e electron !ithdra!in" eect on the rin" makin" the nitro"en less %asic than the nitro"en' %' /he side chain has an inducti&e electron donatin" eect on the rin" makin" the nitro"en less %asic than the nitro"en' c' /he side chain has an inducti&e electron !ithdra!in" eect on the rin" makin" the nitro"en less %asic than the nitro"en' d' /he side chain has an inducti&e electron donatin" eect on the rin" makin" the nitro"en less %asic than the nitro"en' Type: multiple choice question Title: Chapter 22 Question 09 09) /here are t!o possi%le tautomers or histamine' What !ould %e the eect on the tautomer population i a methyl "roup !ere to %e placed at position * o the rin"# Feedback: /he methyl "roup has an inducti&e eect !hich is electron donatin"' /he nitro"en is closer to this su%stituent than the nitro"en and so the nitro"en e3periences this inducti&e eect to a "reater e3tent' /his makes the nitro"en more %asic and more likely to use its lone pair o electrons to %ond to hydro"en' Page reference: )43 a' /he relati&e population o 0 !ould increase' %' /here !ould %e no dierence' ,c' /he relati&e population o A !ould increase' d' It is not possi%le to predict the eect' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Type: multiple choice question Title: Chapter 22 Question 0: 0:) /here are t!o possi%le tautomers or histamine' A methyl "roup at position * plays an important role in a&ourin" tautomer A throu"h an inducti&e eect' What other important eect arises rom the presence o a methyl "roup at position *# Feedback: It introduces selecti&ity or the .2 receptor and is present in anti+ulcer dru"s such as cimetidine' Page reference: )43 a' It introduces selecti&ity or the .1 receptor' ,%' It introduces selecti&ity or the .2 receptor' c' It protects the molecule rom meta%olism' d' It increases the a%ility o the compound to cross cell mem%ranes' Type: multiple choice question Title: Chapter 22 Question 0; 0;) What eect does histamine ha&e on the release o "astric acid# Feedback: .istamine interacts !ith histamine .2 receptors to increase "astric acid secretion' Page reference: )*3 ,a' It increases secretion %' It decreases secretion c' It has no eect d' It completely s!itches o secretion Type: multiple choice question Title: Chapter 22 Question 10 10) What eect !ould a histamine .2 anta"onist ha&e on the release o "astric acid# Feedback: An .2 anta"onist !ould pre&ent histamine acti&atin" the .2 receptor and so "astric acid secretion !ould decrease' It !ould not %e stopped completely since "astric acid and acetylcholine are still a%le to stimulate "astric acid secretion' Page reference: )*3+)** a' It !ould increase secretion ,%' It !ould decrease secretion c' It !ould ha&e no eect d' It !ould stop secretion completely Type: multiple choice question Title: Chapter 22 + Question 11 11) N +-uanylhistamine is a partial a"onist at the .2 receptor' What is meant %y a partial a"onist# a' /he structure is !eakly %ound to the receptor %indin" site' Feedback: incorrect' /his only states that the structure is %indin" to the receptor and does not identiy !hether this %indin" is associated !ith a"onist or anta"onist acti&ity' Page reference: )*)+)*: %' /he structure only occupies a portion o the receptor %indin" site' Feedback: incorrect' /his only states that the structure is %indin" to the receptor and does not identiy !hether this %indin" is associated !ith a"onist or anta"onist acti&ity' Page reference: )*)+)*: OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e ,c' /he structure is %ound to the receptor %indin" site %ut does not ully acti&ate the receptor' Feedback: Correct' /his is the most accurate description o the our' Page reference: )*)+)*: d' /he structure %inds to the receptor$ pre&ents the natural messen"er rom %indin" and eliminates any inherent acti&ity associated !ith the receptor' Feedback: incorrect' /his descri%es an in&erse a"onist !hich %inds to sta%ilise an inacti&e conormation o the receptor' Page reference: )*)+)*: Type: multiple choice question Title: Chapter 22 Question 12 12) N+-uanylhistamine !as the irst lead compound or the de&elopment o .2+anta"onists' What strate"y !as used in de&elopin" the "uanidine structure <A)# Feedback: =3tension indicates the addition o a ne! unctional "roup to ind an e3tra %indin" re"ion' .ere$ the unctional "roup is already present and has %een mo&ed urther a!ay rom the imida1ole rin" %y chain e3tension' 8u%stituent &ariation and isosteric replacement indicate the replacement o a "roup !ith another "roup !hich has not occurred here' Page reference: )*; a' =3tension ,%' Chain e3tension c' 8u%stituent &ariation d' Isosteric replacement Type: multiple choice question Title: Chapter 22 Question 13 13) N+-uanylhistamine !as the irst lead compound or the de&elopment o .2+anta"onists' What !as the rationale or the strate"y used in de&elopin" the "uanidine structure <A)# Feedback: /he anta"onist %indin" re"ion is urther a!ay rom the imida1ole %indin" re"ion than the a"onist %indin" re"ion' /hereore$ e3tendin" the distance %et!een the "uanyl "roup and the imida1ole rin" increases the chances that the molecule !ill %ind as an anta"onist rather than as an a"onist' Page reference: )*; a' /o reduce the inducti&e eect o the "uanidine unit on the imida1ole rin"' %' /o increase the le3i%ility o the chain %y allo!in" more sin"le %ond rotations' c' /o mo&e the %indin" "roup closer to the a"onist %indin" re"ion and a!ay rom the anta"onist %indin" re"ion' ,d' /o mo&e the %indin" "roup closer to the anta"onist %indin" re"ion and a!ay rom the a"onist %indin" re"ion' Type: multiple choice question Title: Chapter 22 Question 1* 1*) >urin" the search or .2 anta"onists$ the ollo!in" %indin" theory !as proposed %et!een a "uanidine unit and a car%o3ylate unit in the %indin" site' What !as it called# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: /he %indin" theory !as called the chelation %indin" theory and in&ol&es the "uanidine and car%o3ylate ion interactin" throu"h ionic and hydro"en %ondin" interactions' Page reference: )*:+)*; a' Ionic %indin" theory %' .ydro"en %ondin" theory ,c' Chelation %indin" theory d' Comple3ation %indin" theory Type: multiple choice question Title: Chapter 22 Question 14 14) /he ollo!in" structures sho! some o the important molecules leadin" to the disco&ery o structure 0' What sort o unctional "roup has %een introduced in 8?@A ;14:1# Feedback: /he unctional "roups descri%ed in the options are as sho!n %elo!: Page reference: )40+)41 a' -uanidine %' 7rea ,c' /hiourea d' /hioamide Type: multiple choice question Title: Chapter 22 Question 1) 1)) /he ollo!in" structures sho! some o the important molecules leadin" to the disco&ery o structure 0' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e A unctional "roup has %een introduced in 8?@A ;14:1' What !as the rationale or introducin" this unctional "roup# Feedback: 8tructure 0 is %urimamide' /he rationale !as to replace the %asic "uanyl "roup !ith a neutral "roup such that it !ould interact %y hydro"en %ondin" rather than ionic %ondin"' A neutral "roup !as chosen that !as as similar as possi%le to the "uanyl "roup in terms o si1e and shape' Page reference: )40+)41 a' /o reduce the num%er o possi%le hydro"en %ond donors present' ,%' /o replace an ionic "roup !ith a neutral "roup' c' /o chan"e the shape o the terminal unctional "roup' d' /o chan"e the si1e o the terminal unctional "roup' Type: multiple choice question Title: Chapter 22 Question 19 19) /he ollo!in" structures sho! some o the important molecules leadin" to the disco&ery o structure 0' What !as the rationale or the strate"y used in de&elopin" structure 0 rom 8?@A ;14:1# Feedback: 8tructure 0 is %urimamide' /he anta"onist %indin" re"ion is urther a!ay rom the imida1ole %indin" re"ion than the a"onist %indin" re"ion' /hereore$ e3tendin" the distance %et!een the thiourea "roup and the imida1ole rin" increases the chances that the molecule !ill %ind as an anta"onist rather than an a"onist' Page reference: )41 a' /o reduce the inducti&e eect o the terminal unctional "roup on the imida1ole rin"' %' /o increase the le3i%ility o the chain %y allo!in" more sin"le %ond rotations' c' /o mo&e the terminal unctional "roup closer to the a"onist %indin" re"ion and a!ay rom the anta"onist %indin" re"ion' ,d' /o mo&e the terminal unctional "roup closer to the anta"onist %indin" re"ion and a!ay rom the a"onist %indin" re"ion' Type: multiple choice question Title: Chapter 22 Question 1: 1:) /he ollo!in" dia"ram sho!s the &arious tautomers o the terminal unctional "roup in structure cimetidine ' Which is considered to %e the most sta%le tautomer# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: 8ince the electron !ithdra!in" eect o the cyanide "roup is inducti&e$ it is e3perienced most %y the nitro"en directly attached to cyanide' As a result$ this nitro"en !ill %e the least %asic o the three nitro"ens present in the "uanidine moiety and the least likely to %ond to hydro"en' Page reference: )4) a' /automer I ,%' /automer II c' /automer III d' /hey are all eBual in sta%ility Type: matching question Title: Chapter 22 + Question 1; 1;) /he ollo!in" synthetic route has %een used to produce cimetidine' What rea"ents !ere used in steps A$ 0 and C# Feedback: Cithium aluminium hydride is a po!erul reducin" a"ent capa%le o reducin" car%onyl "roups such as esters' =sters are reduced to primary alcohols' .ydro"en %romide is used to con&ert an alcohol to an alkyl %romide !hich can then under"o nucleophilic su%stitution !ith 2+aminoethanethiol' Methylamine in ethanol is used to su%stitute the methylthio "roup in the penultimate structure !ith a methylamino "roup' Page reference: )49 a' 8tep A 2 Cithium aluminium hydride %' 8tep 0 2 *:D hydro"en %romide and 2+aminoethanethiol c' 8tep C 2 Methylamine in ethanol Type: multiple choice question Title: Chapter 22 Question 20 20) /he ollo!in" "raph measures lo"<acti&ity) &ersus lo" P' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e What is measured %y lo" P# Feedback: Co" P measures the o&erall hydropho%icity o a molecule' Page reference: )4:+)4; a' 8i1e ,%' .ydropho%icity c' 0asicity d' >ipole moment Type: multiple choice question Title: Chapter 22 Question 21 21) /he ollo!in" "raph measures lo"<acti&ity) &ersus lo" P' What does the "raph indicate a%out a urea "roup in comparison to an N+methyl urea "roup# Feedback: Co" P is a measure o a dru"Es hydropho%icity' Increasin" &alues o lo"P indicate increasin" hydropho%icity and so the urea "roup is more hydropho%ic than an (+methyl urea "roup' Page reference: )4:+)4; a' /he urea "roup is smaller %' /he urea "roup is less %asic c' /he urea "roup is more hydropho%ic ,d' /he urea "roup is less hydropho%ic OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Type: multiple choice question Title: Chapter 22 Question 22 22) /he ollo!in" "raph measures lo"<acti&ity) &ersus lo" P' What does the "raph sho! a%out acti&ity# Feedback: As lo"P increases$ acti&ity increases' Co"P is a measure o hydropho%icity and so increased acti&ity is associated !ith increasin" hydropho%icity' Page reference: )4:+)4; ,a' Acti&ity increases !ith hydropho%ic character %' Acti&ity decreases !ith hydropho%ic character c' Acti&ity increases !ith %asicity d' Acti&ity increases !ith the si1e o the "roup Type: multiple choice question Title: Chapter 22 Question 23 23) /he ollo!in" "raph measures lo"<acti&ity) &ersus lo" P' /he nitroketeneaminal "roup does not it the strai"ht line' Which o the ollo!in" statements is true# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: /he lo" P &alue or this "roup is relati&ely lo! and the compound should ha&e a lo!er acti&ity than it actually has' Page reference: )4;+))0 ,a' /he acti&ity is too "reat or the hydropho%icity o the "roup' %' /he acti&ity is too "reat or the si1e o the "roup' c' /he acti&ity is too "reat or the %asicity o the "roup' d' /he acti&ity is too small or the hydropho%icity o the "roup' Type: multiple choice question Title: Chapter 22 Question 2* 2*) /he ollo!in" "raph measures lo"<acti&ity) &ersus lo" P' What physical eature other than lo"P is important to the acti&ity o cimetidine analo"ues# Feedback: /o %e precise$ the orientation o the dipole moment is important to the acti&ity rather than the si1e o the dipole moment' Page reference: ))0 a' .ydropho%icity %' 0asicity c' Molecular !ei"ht ,d' >ipole moment Type: multiple choice question Title: Chapter 22 Question 24 24) /he ollo!in" "raph measures lo"<acti&ity) &ersus lo" P' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e /he nitroketeneaminal "roup does not it the line o the "raph' /his "roup is present in a clinically important anti+ulcer dru"' Identiy the dru"' Feedback: Fanitidine has the ollo!in" structure Page reference: ))2 ,a' Fanitidine %' Aamotidine c' Camitidine d' Co3tidine Type: multiple choice question Title: Chapter 22 Question 2) 2)) A Q8AF study o cimetidine analo"ues !ith dierent planar "roups produced the ollo!in" eBuationG
lo" <Acti&ity) 2 ;'12 cos H 0')lo"P +2'91' What is the rele&ance o the cos entry# Feedback: /he cos entry Buantiies the orientation o a dipole moment' is the de&iation in an"le o the dipole moment rom the ideal orientation o 30 o ' Page reference: ))0+))1 ,a' It Buantiies the orientation o a dipole moment %' It Buantiies the ma"nitude o a dipole moment c' It Buantiies the orientation o hydro"en %onds d' It Buantiies the stren"th o hydro"en %ondin" Type: multiple choice question Title: Chapter 22 Question 29 29) A Q8AF study o cimetidine analo"ues !ith dierent planar "roups produced the ollo!in" eBuationG
lo" <Acti&ity) 2 ;'12 cos H 0')lo"P +2'91' What is the ideal &alue o ? Feedback: At 0 o $ cos is eBual to a ma3imum &alue o 1' At any other &alue$ the cos &alue !ill %e a raction' /his means that the calculated acti&ity !ill %e smaller' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Page reference: ))0+))1 ,a' 0 o %' *4 o c' )0 o d' ;0 o Type: multiple choice question Title: Chapter 22 Question 2: 2:) What en1yme catalyses the ollo!in" reaction# Feedback: Car%onic anhydrase catalyses the ormation o car%onic acid rom !ater and car%on dio3ide' /he acid dissociates to "i&e a proton and a hydro"en car%onate ion' Page reference: ))4 a' Car%onic synthase %' Car%onic li"ase ,c' Car%onic anhydrase d' Car%onic hydrolase Type: multiple choice question Title: Chapter 22 Question 2; 2;) What reaction is catalysed to po!er the proton pump# Feedback: .ydrolysis o A/P to A>P in&ol&es the splittin" o the terminal phosphate "roup rom the triphosphate chain o A/P$ "eneratin" ener"y !hich can %e used to po!er the proton pump' Page reference: ))4 ,a' A/P to A>P %' A/P to AMP c' A/P to cyclic AMP d' A/P to adenosine Type: multiple choice question Title: Chapter 22 Question 30 30) /he proton pump inhi%itors are prodru"s' Where do they "et acti&ated# Feedback: /he proton pump inhi%itors are acti&ated %y stron" acidic conditions ound only in the canaliculae o parietal cells' Page reference: ))) a' In the li&er %' In the %lood supply c' In parietal cells ,d' In the canaliculae o parietal cells Type: multiple choice question Title: Chapter 22 Question 31 31) What is the typical pK a or proton pump inhi%itors# Feedback: /he proton pump inhi%itors are !eak %ases and reBuire stron" acidic conditions %eore they protonate and %ecome acti&ated' Page reference: ))) ,a' * %' ) c' 9'* d' ; Type: multiple choice question Title: Chapter 22 Question 32 32) What conditions are reBuired to acti&ate proton pump inhi%itors# Feedback: /he proton pump inhi%itors are !eak %ases and reBuire stron" acidic conditions %eore they protonate and %ecome acti&ated' Page reference: ))) OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e ,a' 8tron"ly acidic conditions %' Weakly acidic conditions c' (eutral conditions d' 8li"htly %asic conditions Type: multiple choice question Title: Chapter 22 Question 33 33) /he ollo!in" dia"ram sho!s the de&elopment o the irst commercially a&aila%le proton pump inhi%itor omepra1ole <A)
What sort o heterocyclic rin" !as introduced in .12*I)# Feedback: /he &arious rin"s descri%ed are sho!n %elo!' /he term imida1o%en1ene is incorrect and is not a reco"nised term' Page reference: ))9 a' Quina1oline %' Imida1o%en1ene ,c' 0en1imida1ole d' Indole Type: multiple choice question Title: Chapter 22 Question 3* 3*) /he ollo!in" dia"ram sho!s the de&elopment o the irst commercially a&aila%le proton pump inhi%itor omepra1ole <A)' >urin" this study$ timopra1ole !as ound to %e a promisin" lookin" candidate' Addition o methyl and metho3y su%stituents to the pyridine rin" increases the acti&ity o timopra1ole' What eect do these "roups ha&e# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: /he acti&ation o the dru" under acidic conditions reBuires the pyridine nitro"en to act as a %ase' /he addition o electron donatin" su%stituents increases the %asicity o the pyridine nitro"en' Page reference: )): a' /hey it into hydropho%ic %indin" pockets in the acti&e site and increase %indin" stren"th' ,%' /hey are electron donatin" "roups and increase the %asicity o the pyridine rin"' c' /hey act as steric shields to pre&ent meta%olism at e3posed re"ions o the pyridine rin"' d' /hey %lock the dru" %indin" to alternati&e tar"ets' Type: multiple choice question Title: Chapter 22 Question 34 34) /he ollo!in" dia"ram sho!s the de&elopment o the irst commercially a&aila%le proton pump inhi%itor omepra1ole <A)' >urin" this study$ it !as ound that the methyl and metho3y su%stituents on the pyridine rin" had an important role in increasin" acti&ity' What eect !ould you predict i the pyridine su%stituents in omepra1ole <A) !ere placed as sho!n %elo!# Feedback: /he metho3y su%stituent can interact !ith the pyridine rin" %y resonance' When the su%stituent is located at the para position$ a resonance structure can %e dra!n !here a ne"ati&e char"e is placed on the pyridine nitro"en$ thus increasin" its %asic character and the acti&ity o the compound' I OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e the su%stituent is at the meta position$ this resonance structure is no lon"er possi%le' /his means that the pyridine rin" !ill %e less %asic and the structure !ill %e less acti&e' Page reference: )):+)); a' Acti&ity !ould %e unaected %' Acti&ity !ould increase ,c' Acti&ity !ould decrease d' It is impossi%le to predict !hat !ould happen Type: multiple choice question Title: Chapter 22 Question 3) 3)) /he ollo!in" structure has %een marketed as the more acti&e enantiomer o a proton pump inhi%itor' What is the name o this structure# Feedback: /he structure sho!n is the 8+enantiomer o omepra1ole and this !as !hat led to the structure %ein" called esomepra1ole' Page reference: )); a' =spantopra1ole %' =slansopra1ole ,c' =somepra1ole d' =sra%epra1ole Type: multiple choice question Title: Chapter 22 Question 39 39) /he ollo!in" structure <esomepra1ole) has %een marketed as the more acti&e enantiomer o omepra1ole' What is the name o the strate"y !here a clinically important racemic dru" is replaced !ith the acti&e enantiomer o the dru"# Feedback: Chiral s!itchin" has %een used on se&eral dru"s !hich !ere pre&iously marketed as racemates' Page reference: )); a' Patent s!itchin" %' =nantiomeric s!itchin" c' Asymmetric s!itchin" ,d' Chiral s!itchin" Type: matching question Title: Chapter 22 + Question 3: 3:) /he ollo!in" dia"ram sho!s the synthetic route to an important proton pump inhi%itor' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e What !ere the rea"ents used or step A and step 0 Feedback: 8odium hydro3ide con&erts the thiol to a thiolate !hich can then displace the chloride rom the alkyl chloride &ia a nucleophilic su%stitution reaction' /he meta+chloroper%en1oic acid is an o3idisin" a"ent !hich is oten used as an epo3idisin" a"ent$ %ut !hich in this case is used to o3idise the sulphur atom o the penultimate compound' Page reference: )90 a' 8tep A 2 8odium hydro3ide %' 8tep 0 2 Meta+chloroper%en1oic acid Type: multiple choice question Title: Chapter 22 Question 3; 3;) What type o triple therapy is most commonly used to treat ulcers caused %y Helicobacter pylori# Feedback: /he proton pump inhi%itor ser&es to reduce the Buantity o hydrochloric acid released into the stomach %y parietal cells' /he anti%acterial a"ents are used to com%at the %acterium Helicobacter pylori !hich is kno!n to cause inlammation and cell dama"e in the stomach' Page reference: )92 a' An .2 anta"onist$ proton pump inhi%itor and an anti%acterial a"ent %' An .2 anta"onist$ and t!o anti%acterial a"ents ,c' A proton pump inhi%itor and t!o anti%acterial a"ents d' /!o proton pump inhi%itors and an anti%acterial a"ent Type: multiple choice question Title: Chapter 22 + Question *0 *0) Which o the ollo!in" structures represents histamine at physiolo"ical p.# Feedback: /he side chain nitro"en is ully ionised and the heterocyclic nitro"ens are not ionised' Page reference: )**+)*4 ,a' 8tructure A %' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question *1 OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e *1) Which nitro"en atom <or atoms) in histamine is I are considered important or .2+a"onist acti&ity %ut not .1 acti&ity# Feedback: /he nitro"en atom is in&ol&ed in a hydro"en %ondin" interaction !ith the .2 receptor %ut not the .1 receptor' /he nitro"en atom is in&ol&ed in hydro"en %ondin" interactions !ith %oth the .1 and .2 receptor %indin" sites$ !hile the ionised ammonium "roup at the end o the alkyl chain is in&ol&ed in an ionic interaction !ith %oth %indn" sites' Page reference: )*4+)*) a' /he nitro"en atom and the nitro"en atom %' /he nitro"en atom ,c' /he nitro"en atom d' /he nitro"en atom Type: multiple choice question Title: Chapter 22 + Question *2 *2) 8e&eral %indin" re"ions !ere proposed to %e present in the %indin" site o the .2 receptor' Which o the ollo!in" statements is incorrect# Feedback: /he imida1ole %indin" re"ion is the same or a"onists and anta"onists' Page reference: )*4+)*) ,a' /here are t!o %indin" re"ions or the imida1ole rin" o histamine analo"ues$ one !hich is occupied %y a"onists and one !hich is occupied %y anta"onists' %' /here is a %indin" re"ion !hich interacts ionically !ith the +nitro"en o histamine and results in a"onist acti&ity' c' /here is a %indin" re"ion urther a!ay rom the imida1ole rin" that produces an anta"onist eect i occupied' d' /he +nitro"en o histamine can only %ind to the a"onist %indin" re"ion !hile the "uanyl "roup o N+ "uanylhistamine can %ind either to the anta"onist %indin" re"ion or the a"onist %indin" re"ion' Type: multiple choice question Title: Chapter 22 + Question *3 *3) /he ollo!in" structures are some o the important molecules leadin" to the disco&ery o cimetidine' In !hat order !ere these compounds de&eloped# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: 8tructure C is %urimamide' 8tructure 0 is N +"uanylhistamine' 8tructures A and > are compounds that !ere de&eloped rom N +"uanylhistamine and !hich led to the disco&ery o %urimamide' Page reference: )*)+)4* a' A$ 0$ >$ C %' 0$ A$ C$ > ,c' 0$ A$ >$ C d' 0$ >$ A$ C Type: multiple choice question Title: Chapter 22 + Question ** **) /he ollo!in" structures are some o the important molecules leadin" to the disco&ery o cimetidine' Which o the structures sho!n is %urimamide# Feedback: 8tructure C is %urimamide' 8tructure 0 is N +"uanylhistamine' 8tructures A and > are compounds that !ere de&eloped rom N +"uanylhistamine and !hich led to the disco&ery o %urimamide' Page reference: )*)+)4* a' 8tructure A %' 8tructure 0 ,c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question *4 *4) /he ollo!in" structures are some o the important molecules leadin" to the disco&ery o cimetidine' Which o the structures sho!n is N +"uanylhistamine# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: 8tructure 0 is N+"uanylhistamine' 8tructure C is %urimamide' 8tructures A and > are compounds that !ere de&eloped rom N+"uanylhistamine and !hich led to the disco&ery o %urimamide Page reference: )*)+)4* a' 8tructure A ,%' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question *) *)) /he ollo!in" structures are some o the important molecules leadin" to the disco&ery o cimetidine' Which o the ollo!in" statements is true# Feedback: 8tructure 0 is N +"uanylhistamine' 8tructure C is %urimamide' 8tructures A and > are compounds that !ere de&eloped rom N+"uanylhistamine and !hich led to the disco&ery o %urimamide' Page reference: )*)+)4* a' 8tructure 0 !as de&eloped rom structure A usin" a chain e3tension strate"y' %' 8tructure C !as de&eloped rom structure > usin" a %io+isostere strate"y' c' 8tructure > !as de&eloped rom structure A usin" a chain e3tension strate"y' ,d' 8tructure C !as de&eloped rom structure > usin" a chain e3tension strate"y' Type: multiple choice question Title: Chapter 22 + Question *9 *9) /he ollo!in" structures sho! some o the important molecules leadin" to the disco&ery o structure 0' Which o the ollo!in" statements concernin" structure 0 is untrue# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: It esta%lished that %indin" to the anta"onist %indin" re"ion in&ol&ed hydro"en %ondin" and not ionic %ondin"' Page reference: )40+)41 a' It esta%lished the e3istence o .2+receptors' %' It !as a "ood anta"onist at .2 receptors !ith no a"onist acti&ity' c' It inhi%ited "astric acid release rom parietal cells' ,d' It indicated that %indin" to the anta"onist %indin" re"ion in&ol&ed ionic %ondin" and not hydro"en %ondin"' Type: matching question Title: Chapter 22 + Question *: *:) Identiy the ollo!in" structures Feedback: 0urimamide !as the irst o the our compounds named to %e de&eloped and esta%lished the e3istence o .2 receptors' /hia%urimamide !as de&eloped %y introducin" a sulphur atom into the side chain o %urimamide' Metiamide in&ol&ed the urther addition o a methyl su%stituent to the imida1ole rin" and cimetidine in&ol&ed replacement o the thiourea "roup !ith cyano"uanidine "roup' Page reference: )40+)44 a' Cimetidine 2 8tructure 0 %' /hia%urimamide 2 8tructure C c' Metiamide 2 8tructure > d' 0urimamide 2 8tructure A Type: multiple choice question Title: Chapter 22 J Question *; *;) Which o the ollo!in" structures has an electron donatin" side chain attached to the imida1ole rin"# Feedback: /he structures sho!n <A+>) are %urimamide$ cimetidine$ thia%urimamide and metiamide respecti&ely' 0urimamide has an electron donatin" side chain' /he other structures contain sulur in the side chain$ makin" the su%stituent electron !ithdra!in"' Page reference: )40+)44 OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e ,a' 8tructure A %' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 J Question 40 40) /he ollo!in" structures !ere part o a study aimed at indin" anti+ulcer a"ents' What sort o mode o action do they ha&e# Feedback: /he structures sho!n <A+>) are %urimamide$ cimetidine$ thia%urimamide and metiamide respecti&ely' /hey all act as anta"onists at the .2 receptor' Page reference: )40+)44 a' /hey are receptor a"onists ,%' /hey are receptor anta"onists c' /hey are en1yme inhi%itors d' /hey %lock carrier proteins Type: multiple choice question Title: Chapter 22 J Question 41 41) /he ollo!in" structures !ere part o a study aimed at indin" anti+ulcer a"ents' What is their tar"et# Feedback: /he structures sho!n <A+>) are %urimamide$ cimetidine$ thia%urimamide and metiamide respecti&ely' /hey all act as anta"onists at the .2 receptor' Page reference: )40+)44 a' /he proton pump %' /he .1 receptor ,c' /he .2 receptor d' /he "astrin receptor OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Type: multiple choice question Title: Chapter 22 + Question 42 42) /he ollo!in" structures !ere part o a study aimed at indin" anti+ulcer a"ents' Which o the structures has the p? a or the imida1ole rin"# Feedback: /he structures sho!n <A+>) are %urimamide$ cimetidine$ thia%urimamide and metiamide respecti&ely' 0urimamide has an electron donatin" side chain "i&in" it a p?a o 9'24' /he other structures contain sulur in the side chain$ makin" the su%stituent electron !ithdra!in"' /hia%urimamide has a p?a o )'24' Metiamide has an electron donatin" methyl "roup !hich counteracts the electron !ithdra!in" inluence o the side chain "i&in" it a p?a o )':0' Aor the same reson$ the p?a or the imida1ole rin" o cimetidine is also hi"her than the p?a or thia%urimamide Page reference: )40+)44 a' 8tructure A %' 8tructure 0 ,c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question 43 43) /he ollo!in" structures !ere part o a study aimed at indin" anti+ulcer a"ents' In !hat order !ere the structures de&eloped# Feedback: /he structures sho!n <A+>) are %urimamide$ cimetidine$ thia%urimamide and metiamide respecti&ely' Page reference: )40+)44 a' C$ A$ 0$ > %' 0$ >$ C' A ,c' A$ C$ >$ 0 d' >$ 0$ C$ A OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Type: multiple choice question Title: Chapter 22 + Question 4* 4*) /he ollo!in" structure is cimetidine' Which electron donatin" "roup is present to a&our the acti&e tautomeric orm o the imida1ole rin" sho!n# Feedback: /he methyl "roup has an inducti&e electron donatin" eect on the imida1ole rin"' /his inducti&e eect is more pronounced at the +nitro"en than the +nitro"en since the ormer is closer to the su%stituent' /he inducti&e eect makes the +nitro"en more %asic and a&ours the tautomer !here this nitro"en is %onded to a hydro"en' Page reference: )41+)44 ,a' -roup a %' -roup % c' -roup c d' -roup d Type: multiple choice question Title: Chapter 22 + Question 44 44) /he ollo!in" structure is cimetidine' Which electron !ithdra!in" "roup is present to a&our the acti&e tautomeric orm o the imida1ole rin" sho!n# Feedback: /he sulur has an inducti&e electron !ithdra!in" eect on the imida1ole rin"' /his inducti&e eect is more pronounced at the +nitro"en than the +nitro"en since the ormer is closer to the su%stituent' /he inducti&e eect makes the +nitro"en more %asic and a&ours the tautomer !here this nitro"en is %onded to a hydro"en' Page reference: )41+)44 a' -roup a ,%' -roup % c' -roup c d' -roup d Type: multiple choice question Title: Chapter 22 + Question 4) 4)) /he ollo!in" structure is cimetidine' Which "roup is present to interact !ith a hydro"en %ondin" re"ion not used %y histamine# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: -roup d is a naturally occurrin" moiety !hich is neutral and interacts !ith a %indin" re"ion throu"h hydro"en %ondin"' It !as used to replace a thiourea "roup in pre&ious structures since the latter !as responsi%le or to3ic side eects' Page reference: )41+)44 a' -roup a %' -roup % c' -roup c ,d' -roup d Type: multiple choice question Title: Chapter 22 + Question 49 49) /he ollo!in" structure is cimetidine' /he "uanidine moiety at the end o the side chain is neutral !hich is unusual since "uanidine moieties are usually %asic' Which one o the coloured "roups sho!n is responsi%le or this# Feedback: /he cyanide "roup has a stron" inducti&e eect !hich is electron !ithdra!in"' As a result the %asicity o the "uanidine "roup is reduced and it is less likely to ionise' Page reference: )4*+)44 ,a' -roup a %' -roup % c' -roup c d' -roup d Type: multiple choice question Title: Chapter 22 + Question 4: 4:) Which o the ollo!in" structures is a meta%olite o cimetidine# Feedback: /he meta%olites o cimetidine are sho!n %elo!' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Page reference: )4) ,a' 8tructure A %' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question 4; 4;) Which o the ollo!in" structures is a meta%olite o cimetidine# Feedback: /he meta%olites o cimetidine are sho!n %elo!' Page reference: )4) a' 8tructure A %' 8tructure 0 c' 8tructure C ,d' 8tructure > Type: matching question Title: Chapter 22 + Question )0 )0) /he synthetic route to cimetidine is sho!n %elo!: OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Match the structures sho!n %elo! to the a%o&e synthetic route' Feedback: /he synthesis o cimetidine is a * sta"e process in&ol&in" the construction o cimetidineEs side chain on a startin" material already containin" the reBuired imida1ole rin"' Page reference: )49 a' A 2 8tructure III %' 0 2 8tructure II c' C 2 8tructure I d' > 2 8tructure IK Type: multiple choice question Title: Chapter 22 + Question )1 )1) /he ollo!in" conormation or the cyano"uanidine "roup o cimetidine is not a&oured due to a %ad steric interaction' Which o the ollo!in" dia"rams illustrates this# Feedback: In dia"ram A$ the methyl "roup is too close to the side chain' In the other dia"rams$ there is &ery little steric interaction since one o the "roups in&ol&ed is a small hydro"en' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Page reference: )4)+)4: ,a' >ia"ram A %' >ia"ram 0 c' >ia"ram C d' >ia"ram > Type: multiple choice question Title: Chapter 22 + Question )2 )2) /he ollo!in" dia"ram sho!s the synthetic route to omepra1ole' What !ere the unctional "roups L and M# Feedback: /he thiol "roup is con&erted to a thiolate ion in the presence o sodium hydro3ide and acts as a nucleophile to displace a chloride ion rom the alkyl chloride' Page reference: )90 a' L28.$ M2Cl ,%' L2Cl$ M28. c' L28Cl$ M2Ci d' L2Ci$ M28Cl Type: multiple choice question Title: Chapter 22 + Question )3 )3) /he ollo!in" dia"ram sho!s &arious conormations or the cyano"uanidine "roup o cimetidine' A study !as carried out to ind out the most sta%le conormations' Which o the ollo!in" statements is true# Feedback: /he study sho!ed that the =N and N= tautomers !ere a&oured and that the NN and == tautomers !ere not' /his demonstrated that t!o hydro"en %ondin" interactions !ere takin" place to t!o dierent hydro"en %ondin" "roups in the %indin" site$ thus dispro&in" the chelation %ondin" theory' Page reference: )4)+)4: a' /he study sho!ed that only the Z,E tautomer is a&oured' %' /he study esta%lished that there is only one hydro"en %ondin" interaction %et!een the "uanidine unit and the %indin" re"ion' c' /he study sho!ed that only the E,Z tautomer is a&oured' ,d' /he study dispro&ed the chelation theory o hydro"en %ondin"' Type: matching question OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Title: Chapter 22 J Question )* )*) /he ollo!in" dia"ram sho!s a parietal cell releasin" .Cl into the stomach' Identiy A+>' Feedback: /he proton pump is responsi%le or pumpin" protons out o the parietal cell and potassium ions into the parietal cell' Acetylcholine is a neurotransmitter that interacts !ith choliner"ic receptors on parietal cells to increase the release o hydrochloric acid into the stomach' /he hormone "astrin and the local hormone histamine ha&e the same eect !hen they interact !ith their correspondin" receptors' Page reference: ))*+))4 a' -astrin 2 > %' .istamine 2 0 c' Proton pump 2 A d' Acetylcholine 2 C Type: multiple choice question Title: Chapter 22 + Question )4 )4) /he ollo!in" dia"ram illustrates a parietal cell' What is the eature la%elled A# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: Aeature A is the proton pump responsi%le or pumpin" protons into the lumen o the stomach' Potassium ions are %rou"ht into the parietal cell in e3chan"e and the process is po!ered %y the hydrolysis o A/P' Page reference: ))*+))4 a' /he histamine receptor %' Adenylate cyclase c' An ion channel or chloride ions ,d' /he proton pump Type: matching question Title: Chapter 22 + Question )) ))) /he ollo!in" dia"ram illustrates a parietal cell !here eature A is the proton pump' What are the species la%elled A+># Feedback: Aeature A is the proton pump responsi%le or pumpin" protons into the lumen o the stomach' Potassium ions are %rou"ht into the parietal cell in e3chan"e and the process is po!ered %y the hydrolysis o A/P' Chloride and potassium ions depart the parietal cells throu"h ion channels !hich are separate rom the proton pump' Page reference: ))*+))4 a' .ydrochloric acid 2 > %' Chloride ions 2 C OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e c' Potassium ions 2 0 d' Protons 2 A Type: multiple choice question Title: Chapter 22 + Question )9 )9) /he ollo!in" dia"ram illustrates a parietal cell !here eature A is the proton pump' What is the space indicated %y the la%el =# Feedback: Aeature A is the proton pump responsi%le or pumpin" protons into the lumen o the stomach' Potassium ions are %rou"ht into the parietal cell in e3chan"e and the process is po!ered %y the hydrolysis o A/P' Chloride and potassium ions depart the parietal cells throu"h ion channels !hich are separate rom the proton pump' /he canaliculus is the channel into !hich these ions enter and lea&e' .Cl is released rom the canaliculus into the stomach lumen' Page reference: ))*+))4 a' 8tomach lumen %' Parietal channel ,c' Canaliculus d' Parietal outlet Type: multiple choice question Title: Chapter 22 + Question ): ):) /he ollo!in" structure is the proton pump inhi%itor omepra1ole 6mepra1ole under"oes a series o arran"ements in the acid conditions o the canaliculus %eore reactin" !ith cysteine residues o the the proton pump' Which o the ollo!in" structures is the structure responsi%le or that alkyation# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: /he thiol "roup o cysteine acts as a nucleophile and reacts !ith structure A to produce a disulide co&alent %ond %et!een the amino acid and the dru"' /he other structures sho!n are ormed in the mechanism %y !hich omepra1ole is con&erted to structure A' Page reference: )))+))9 ,a' 8tructure A %' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question ); );) /he ollo!in" mechanism sho!s ho! proton pump inhi%itors are acti&ated' Which arro! is incorrect# Feedback: Arro! 0 is pointin" the !ron" !ay' Curly arro!s represent the mo&ement o electrons' A proton has no electrons and so it ne&er makes sense to dra! an arro! rom a proton' Page reference: )))+))9 a' A ,%' 0 c' C d' > Type: matching question Title: Chapter 22 + Question 90 90) Match the ollo!in" structures !ith the named dru"s: OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: All the e3amples "i&en are proton pump inhi%itors' Page reference: ))4 a' Fa%epra1ole 2 8tructure > %' Cansopra1ole 2 8tructure C c' 6mepra1ole 2 8tructure 0 d' Pantopra1ole 2 8tructure A Type: matching question Title: Chapter 22 Question 91 91) /he ollo!in" dia"ram sho!s some o the structures that !ere rele&ant to the de&elopment o an important antiulcer dru"' Match the structures to the ollo!in" names: Feedback: All the e3amples "i&en are proton pump inhi%itors' Page reference: ))9+)); a' CM(131 2 8tructure 0 %' /imopra1ole 2 8tructure A c' Picopra1ole 2 8tructure > d' 6mepra1ole 2 8tructure C Type: multiple choice question Title: Chapter 22 + Question 92 92) /he ollo!in" dia"ram sho!s some o the structures that !ere rele&ant to the de&elopment o an important antiulcer dru"' Which o these structures !as the lead compound# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: 8tructure 0 is CM(131 !hich !as the lead compound$ %ut suered rom li&er to3icity' Page reference: ))9+)); a' 8tructure A ,%' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 J Question 93 93) /he ollo!in" dia"ram sho!s some o the structures that !ere rele&ant to the de&elopment o an important antiulcer dru"' In !hat order !ere they disco&ered# Feedback: 8tructure 0 is CM(131 !hich !as the lead compound or the study' 8tructures A$ C and > are timopra1ole$ omepra1ole and picopra1ole respecti&ely Page reference: ))9+)); a' A$ 0$ C$ > ,%' 0$ A$ >$ C c' 0$ >$ A$ C d' C$ >$ A$ 0 Type: multiple choice question Title: Chapter 22 + Question 9* 9*) /he ollo!in" dia"ram sho!s some o the structures that !ere rele&ant to the de&elopment o an important antiulcer dru"' Which o these structures !as disco&ered ollo!in" dru" meta%olism studies# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: 8tructure 0 is CM(131 !hich !as the lead compound or the study' 8tructures A$ C and > are timopra1ole$ omepra1ole and picopra1ole respecti&ely' >ru" meta%olism studies led to the reco"nition that the sulur atom in timopra1ole under!ent meta%olic o3idation to produce an acti&e meta%olite' Page reference: ))9+)); ,a' 8tructure A %' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question 94 94) /he ollo!in" dia"ram sho!s some o the structures that !ere rele&ant to the de&elopment o an important antiulcer dru"' Which o these structures !as ound to ha&e a side eect !hich in&ol&ed inhi%ition o iodine uptake %y the thyroid "land# Feedback: 8tructure 0 is CM(131 !hich !as the lead compound or the study' 8tructures A$ C and > are timopra1ole$ omepra1ole and picopra1ole respecti&ely' Page reference: ))9+)); ,a' 8tructure A %' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question 9) 9)) /he ollo!in" molecule is omepra1ole$ an important proton pump inhi%itor' OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Which o the ollo!in" structures is a meta%olite# Feedback: /he t!o maOor meta%olites o omepra1ole are sho!n %elo!' Page reference: )); ,a' 8tructure A %' 8tructure 0 c' 8tructure C d' 8tructure > Type: multiple choice question Title: Chapter 22 + Question 99 99) /he ollo!in" molecule is omepra1ole$ an important proton pump inhi%itor' Which o the ollo!in" structures is a meta%olite# OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed' Patrick: An Introduction to Medicinal Chemistry 3e Feedback: /he t!o maOor meta%olites o omepra1ole are sho!n %elo!' Page reference: )); ,a' 8tructure A %' 8tructure 0 c' 8tructure C d' 8tructure > OXFORD H i g h e r E d u c a t i o n 5 63ord 7ni&ersity Press$ 200)' All ri"hts reser&ed'