Investigations of regio- and stereoselectivities in the synthesis of cytotoxic isoxazolidines through 1,3-dipolar cycloadditions of nitrones to dipolarophiles bearing an allylic oxygen

被引：30
|
作者：
Singh, Rajinder
Bhella, Surinderjit Singh
Sexana, A. K.
Shanmugavel, M.
Faruk, Abdul
Ishar, M. P. S. [1 ]
机构：
[1] Guru Nanak Dev Univ, Dept Pharmaceut Sci, Bioorgan & Photochem Lab, Amritsar 143005, Punjab, India
[2] Reg Res Lab, Div Pharmacol, Jammu 184001, Jammu & Kashmir, India
来源：
TETRAHEDRON | 2007年 / 63卷 / 10期
关键词：
cycloadditions; nitrone; stereoselectivities; secondary interactions; isoxazolidines; anticancer activity;
D O I：
10.1016/j.tet.2006.12.076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regio- and stereoselectivities in cycloadditions of nitrones to dipolarophiles bearing an allylic oxygen, which furnishes substituted-isoxazolidine analogs of the furanose ring of nucleosides, have been investigated. Although the obtained regioselectivities are anticipated, a rationalization of the preferred formation of endo-cycloadducts necessitates the involvement of an allylic oxygen in secondary interaction. The obtained isoxazolidines display cytotoxic activities against a number of human cancer cell lines. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2283 / 2291
页数：9
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