Chemical synthesis of the 17-propanamide derivatives of stereoisomeric Δ14-17α- and 17β-estradiols: potential 17β-hydroxysteroid dehydrogenase inhibitors

被引：3
|
作者：
Iida, Takashi [1 ]
Ogawa, Shoujiro [1 ]
Tamegai, Hideyuki [1 ]
Adachi, Yuuki [1 ]
Saito, Hiroaki [2 ]
Ikegawa, Shigeo [3 ]
Konishi, Hiroaki [4 ]
Takagi, Akimitsu [4 ]
Matsuzaki, Takeshi [4 ]
机构：
[1] Nihon Univ, Dept Chem, Coll Humanities & Sci, Setagaya Ku, Tokyo 3291151, Japan
[2] Nihon Univ, Coll Pharm, Chiba 2748555, Japan
[3] Kinki Univ, Fac Pharmaceut Sci, Higashiosaka, Osaka 5778502, Japan
[4] Yakult Honsha Co Ltd, Yakult Cent Inst Microbiol Res, Tokyo 1868650, Japan
来源：
CHEMISTRY AND PHYSICS OF LIPIDS | 2011年 / 164卷 / 02期
关键词：
Steroid; Estrogen; Estradiol; Estrone; Chemical synthesis; Spiro-gamma-lactone; Propanamide; NMR; 17; beta-HSD; Inhibitor; BILE-ACID; D-RING; DEHYDROGENASE; METABOLITES; ESTRADIOL; STEROIDS;
D O I：
10.1016/j.chemphyslip.2010.11.005
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The 17-propanamide derivatives of diastereomeric Delta(14)-17 alpha- and 17 beta-estradiols, the potential candidates of a 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) inhibitor, were synthesized in 11 steps from estrone. The principal reactions employed involved in (1) conversion of estrone to the corresponding Delta(14)-estrone, (2) Grignard reaction of Delta(14)-estrone with allylmagnesium bromide followed by regioselective hydroboration of the resulting stereoisomeric 17 xi-allyl-Delta(14)-17 xi-ols with 9-borabicyclo[3.3.1]nonane (9-BBN), and (3) direct amidation of the 17 xi-O-/17 xi-C-spiro-gamma-lactones with NH3 under positive pressure of Hz. (C) 2010 Elsevier Ireland Ltd. All rights reserved.
引用
收藏
页码：106 / 112
页数：7
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