Bors. foe Basic Principles of Medicinal Chemistry Lab Second Exam PHR 143P naMe_DOnS Cox November 21, 2000 SSN Part 1. 14 Questions - HPLC, Crown Ether, Metabolism Labs (80 points) Part 2. 15 Questions — Anatomy Labs (40 points) 1. (G points) From the following list, pick ot ONE example of each of the following: A. An Alkali Metal Now B. An Alkaline Earth Metal C. A Transition Metal Li, Na, K, Ca, Mg, Fe, Cu, Co 2. (10 points) A solution of sodium picrate (3 mL) in dichloromethane was diluted with 3.0 mL of acetonitrile. From the resulting solution a 5.0 mL aliquot was removed and diluted to 25.0 mL with 1:1 dichloromethane/acetonitrile. ‘The absorbance of this solution was determined to be 0.6 at 375 nm. Assuming that the molar extinction coefficient (e) for sodium picrate at this wavelength is 20,000 cm-!M-!, what is the sodium picrate concentration of the original dichloromethane solution? Ae tbe 25eb L oes (roeent MYC) C wom KE Swe owt Vmoe oan Tn epee cz bxe mM Bat san? (4 points) Circle the TWO atoms in the molecule below that could be involved in bidentate binding to a metal ion (chelation) QE Ce Ce I °4. (5 points) Which of the following molecules would run faster (higher R, value) on a normal phase (silica gel stationary phase) TLC experiment with a mobile phase of | % methanol (CH,OH) in chloroform (CHCI)? = Ue molabeig, mare neapiler, sort wail ele feck jin Wee non-poor dun. rites 0. ~ polos ~ atabing . aa ~ non.pler — mile L © Nig 5. (10 points) A barbiturate with a pK, of 7.4 was subjected to a reverse phase HPLC experiment using an aqueous mobile phase of pH 7.4 in order to determine the apparent ). The results of this experiment demonstrated that this barbiturate has a Log(P9) of 1.0. What is the intrinsic partition coefficient (Log(?.,)) for partition coefficient (Log(P,, this compound? _. LogPoop= Ligh + lag Lomuntsed) P a le | Loe Leder ley l5d on | loz Lyd + b, 01) Aa I 7+ 50% vented 250% on ime 6. (5 points) The compound shown below has a retention time of 6.0 min. in a reverse phase 2 HPLC experiment using a mobile phase of 1:2 acetonitrile (CH,CN) / phosphate buffer - (pH 4.0). Would the retention time be shorter or longer for this compound if the mobile phase were changed to 1:1 acetonitrile (CH,CN) / phosphate buffer (pH 4.0)? Explain you answer. reese det ¢ thay = en pabe sia Pot bie ple ~y an LF wold TE Hwee wes ves phosphate bolle teach ot We Comper? deers, Seu Ya mbes paler the mt see) add ney (deere SR (aa Dek westLaboratory Questions (Two Labs) From Dr. Davis i 7, (Spoints) Based on our discussion in the drug metabolism lab, which one of the following is NOT a logical pathway for the metabolism of the parent drug, f Hi—C—CH, OH acetaminophen? A. Amide hydrolysis ‘Glucuronidation on the phenol. _)Glucuronidation on the amide. D. Aryl sulfate formation. 8. (S points) A new cephalosporin, cepfotartrin (shown below) is currently under development. Based on our discussion on the metabolism of similar cephalosporins, what can you conclude about this new antibiotic? (Bscpeatsain may lead to a metabolite that could cause an antabuse reaction if @ patient on this antibiotic consumes alcohol. §-Dealkylation may lead to a metabolite that could cause « bleeding episode in a patient who is also on anticoagulant therapy. §:Dealkyiation may lead to a metabolite that could cause convulsions in a patient who a 7 is on anticonvulsant therapy — D. $-Dealkylation will not cause a probiem in the majority of patients taking B