Synthesis and reactivity of azobenzene-based bispropargyl sulfones: Interesting comparison between cyclic and acyclic systems

被引：5

作者：

Mitra, Debarati ^{[1
]}

Kar, Mournita ^{[1
]}

Pal, Rhitankar ^{[1
]}

Basak, Amit ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 731302, W Bengal, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 16期

关键词：

azobenzene; bispropargyl; sulfone; DNA-cleavage; photoisomerization;

D O I：

10.1016/j.bmcl.2007.06.001

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Azobenzene-based bispropargyl bissulfone 3 containing stable E-azo moiety has been synthesized. Upon irradiation with long wavelength UV it isomerized to the Z-form 4, which can be thermally reisomerized to the E-isomer. Reactivity towards isomerization to the allenic system as well as DNA-cleaving efficiency under basic conditions was found to be significantly lower as compared to the previously synthesized cyclic sulfones 1 and 2. This lowering of reactivity can be explained in terms of low conversion to the allenic form and hence the lower extent of alkylation of DNA-bases, the only possible DNA-cleavage pathway for 3 and 4. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：4514 / 4517

页数：4

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