STRUCTURE AND CONFORMATION OF CORTISONE SIDE CHAIN

被引：13

作者：

COOPER, A

DUAX, WL

机构：

[1] Medical Foundation of Buffalo, Buffalo, New York

[2] Computer Task Group Inc., Buffalo, New York

来源：

JOURNAL OF PHARMACEUTICAL SCIENCES | 1969年 / 58卷 / 09期

关键词：

Cortisone side chain–structure; conformation; Crystalline structure data–cortisone side chain conformation; C‐17 side chain conformation–4‐chloro‐derivative; cortisone;

D O I：

10.1002/jps.2600580933

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The results of a recent crystal structure analysis of the 4‐chloro‐derivative of cortisone have been used to describe the exact conformation of the C‐17 side chain in this molecule. The results of this analysis are compared with those obtained from molecular orbital calculations, and from optical rotatory dispersion, circular dichroism, infrared and nuclear magnetic resonance measurements. The C‐17 side chain shows no evidence of internal hydrogen bonding, either with the C‐17 or with the C‐21 hydroxyl groups, and it is shown that such hydrogen bonding is unfeasible, both in the crystal and in solution. Evidence regarding the preferred conformation of C‐17 acyl side chains in general, is also presented. Copyright © 1969 Wiley‐Liss, Inc., A Wiley Company

引用

页码：1159 / &

共 13 条

[1] CONFORMATION OF NON-AROMATIC RING COMPOUNDS .25. GEOMETRY AND CONFORMATION OF RING D IN SOME STEROIDS FROM X-RAY STRUCTURE DETERMINATIONS [J].