Synthesis of novel 16-spiro steroids: Spiro-7′-(aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles

被引：24
|
作者：
Kanchithalaivan, Selvaraj [1 ]
Kumar, Raju Ranjith [1 ]
Perumal, Subbu [1 ]
机构：
[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India
来源：
STEROIDS | 2013年 / 78卷 / 04期
关键词：
Androsterone; 16-Siprosteroids; 1,3-Dipolar cycloaddition; Azomethine ylide; Pyrrolothiazole; 1,3-DIPOLAR CYCLOADDITION; BIOLOGICAL EVALUATION; UNCARIA-RHYNCHOPHYLLA; DERIVATIVES; STEREOCHEMISTRY; FACILE; ISATIN; CELLS;
D O I：
10.1016/j.steroids.2012.12.017
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 1,3-dipolar cycloaddition of azomethine ylide derived in situ from the reaction of acenaphthylene-1,2-dione and 1,3-thiazolane-4-carboxylic acid to various exocyclic dipolarophiles synthesized from trans-androsterone and trans-dehydroandrosterone afforded a library of novel spiro[5'.2 '']acenaphthylene-1 ''-one-spiro[16.6']-(7'-aryl)-tetrahydro-1H-pyrrolo [1,2-c][1,3]thiazolo-trans-androsterone/dehydroandrosterone hybrid heterocycles respectively. These reactions proceeded stereo-specifically affording a single isomer of the 16-spiro steroids in excellent yields. (C) 2013 Elsevier Inc. All rights reserved.
引用
收藏
页码：409 / 417
页数：9
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