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Regioselective Synthesis of the FXR Antagonist E ‐Guggulsterone from Three Natural Steroids
Author(s) -
Chin Jungwook,
Hahn Dongyup,
Won Dong Hwan,
Cho Sung Jin,
Kim KyungHee,
Ham Jungyeob,
Kang Heonjoong
Publication year - 2017
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11120
Subject(s) - farnesoid x receptor , transactivation , chemistry , stereochemistry , testosterone (patch) , antagonist , yield (engineering) , steroid , nuclear receptor , pharmacology , receptor , biochemistry , endocrinology , transcription factor , hormone , biology , physics , gene , thermodynamics
In our attempt to develop a method to synthesize E ‐ and Z ‐guggulsterones [antagonists of farnesoid X receptor ( FXR )], we have succeeded in synthesizing E ‐guggulsterone selectively from three steroids, viz , 4‐androsten‐3, 17‐dione ( 2 ), 5‐androsten‐3β‐ol‐17‐one ( DHEA ) ( 3 ), and testosterone ( 4 ), in 68, 86 and 62% overall yield, respectively. We also investigated the biological effects of the synthetic E ‐ and Z ‐guggulsterones and found that E ‐guggulsterone was more potent than Z ‐guggulsterone in inhibiting FXR transactivation
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