Steroids Synthesis

Steroids are natural chemicals widely found in nature. It is a kind of lipid

compound and characterized by a four ring parent nucleus of all
steroids derived from the acetyl coenzyme A synthesis pathway.
Different steroids are only diverse in their functional groups that
attached to their rings, and their basic structure is the cyclopentane
polyhydric phenanthrene. Commonly used steroids include
phytosterols, bile acids, C21 steroids, insect metamorphic hormones,
cardiac glycosides, steroidal saponins, steroid alkaloids, and toad
venom. Steroids are one of the most important substances in biological
systems, and steroid hormones are combined with their receptor
proteins to produce physiological responses, causing changes in gene
transcription and cell function. In human physiology and pharmacology,
the most important steroids are cholesterol, steroid hormones,
precursors and metabolites, and steroids are responsible for
transporting proteins in the blood. Given the significant importance of
steroids, the synthesis and application of steroids is attracting more and
more attention in pharmaceutical industry.

Fig 1. The general structure of

steroids

 Novel Steroidal Bioconjugates

 Steroids are a class of biomolecules that exist widely and have
important functions in organisms. Its special structure makes the
compounds have lipophilicity, membrane affinity and specific binding
with low density lipoprotein. Using these characteristics, we design and
synthesize steroid conjugates of various drug molecules, which can
increase the liposoluble and improve the transmembrane permeability
of drug molecules. The distribution in specific tissues and the unique
biological activity of steroid conjugates are of great significance for
exploring new bioactive molecules.

Fig 2. Bile acid-ß-amino acid ester conjugates (Peiyuan Jin et al. 2007)

 3-oxo-△4’6 Steroids

3-oxo-△4’6 Steroids are important intermediates in the synthesis of

steroid drugs. The synthesis of this compound is of great significance.
The synthetic methods of 3-oxo-△4’6 Steroids are manganese dioxide
dehydrogenation method, palladium carbon dehydrogenation method
and so on. These methods either involve low overall yield or cause
environmental pollution. Moreover, two chloro two cyanogen quinone
(DDQ) dehydrogenation is not suitable for the synthesis of compounds
with acid sensitive groups on steroid rings. In order to solve the
shortcomings of the above methods, a simple process for one-step
synthesis of 3-oxo-△4’6 Steroids.
 Fig 3.

One-step synthesis of 3-oxo-△4,6 steroids (Xiafei Deng et al. 2007)

 Steroidal Angiogenesis Inhibitors

Steroid alkaloid Cortistatin compounds are another new type of

angiogenesis inhibitor after the marine amino sterol compound
squalamine. Since their unique chemical structure and significant
biological activity have aroused great interest in organic synthesis
chemists, the synthesis of Cortistatin A in more than two years has been
made. It was completed by semi synthesis and total synthesis, and
many strategies for constructing Cortistatin class B marine natural
products were also reported.

Fig 4. Synthesis Route Design of Cortistatin A (Yong Shi et al. 2010)

 Hydroxylated Steroids
 Hydroxylated steroids play an important role in improving drug activity,
cytotoxicity and metabolism of exogenous compounds. However, as an
important pharmaceutical intermediate, hydroxysteroids have a large
market demand, complicated extraction processes, and difficult
chemical synthesis, which is not conducive to the development of
innovative drugs. We hope to solve these problems through
biocatalysis (here refers to Enzymology). Enzyme catalyzed methods
have attracted more and more attention because of the advantages of
short production cycle, high yield, mild reaction conditions, high
regional selectivity and stereoselectivity.

Fig 5.

Synthesis Route Design of androstenedione (1) to 1α-OH-androstenedione (1a) (Xing

Liu et al. 2017)

BOC Sciences is proud to provide you high-quality chemical synthesis

service. Our experts and chemists have been developing and
implementing a wide variety of drug synthesis pathways. We have a
dedicated custom synthesis team, as well as starting materials and
intermediates for various synthetic compounds. In addition, various
techniques (NMR, LCMS, GCMS, HPLC, IR, and X-ray) are used to
analyze the synthesis of the completed compound, and synthesis is in
a short turnaround time. Glad to hear your comments and look forward
to cooperating with you.

References

1. Peiyuan, J. and Yong, J. (2007) ‘Design, synthesis and biological activity of

novel steroidal bioconjugates’, PROGRESS IN CHEMISTRY-BEIJING, 19(12):
1883.
2. Xiafei D., et al. (2007) ‘one-step synthesis of 3-oxo -△4’6 steroids’, Chin Pharm
J, 42: 548-549.
3. Yong, S. and Weisheng, T. (2010) ‘Structure, Bioactivity and Synthesis of
Cortistatin, a New Kind of Steroidal Angiogenesis Inhibitors’, CHINESE
JOURNAL OF ORGANIC CHEMISTRY, 30(4): 515-527.
4. Liu, X. and Kong, J. Q. (2017) ‘Steroids hydroxylation catalyzed by the
monooxygenase mutant 139-3 from Bacillus megaterium BM3’, Acta
Pharmaceutica Sinica B, 7(4): 510-516.