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

页码：106 / 112

页数：7

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