A comparative structural study of the steroid epimers:: 17β-amino-1,3,5(10)-estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol and some derivatives by 1H NMR, and x-ray diffraction analysis

被引：13

作者：

Lemini, C

Cruz-Ramos, E

Toscano, RA

Cruz-Almanza, R

机构：

[1] Univ Nacl Autonoma Mexico, Fac Med, Dept Farmacol, Mexico City 04510, DF, Mexico

[2] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico

来源：

STEROIDS | 1998年 / 63卷 / 11期

关键词：

17-aminosteroids; 17; alpha-aminoestrogens; beta-aminoestrogens; H-1; NMR; x-ray; epimers;

D O I：

10.1016/S0039-128X(98)00063-4

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 epimers 17 beta-amino-1,3,5(10)-estratrien-3-ol and 17 alpha-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17 beta-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone-oxime. The 17 alpha-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17 alpha-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-alpha-amino-1,3,5(10)-estratriene hydrochloride, 17 beta-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17 beta-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17 alpha and 17 beta amino epimers for the first time. (Steroids 63:556-563, 1998) (C) 1998 by Elsevier Science Inc.

引用

页码：556 / 564

页数：9

共 26 条

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