链黑菌素抗生素类似物的合成与细胞毒性
Synthesis and cytotoxicity of leinamycin antibiotic analogues.
作者信息
Szilagyi Akos, Fenyvesi Ferenc, Majercsik Orsolya, Pelyvas Istvan F, Bacskay Ildikó, Fehér Palma, Varadi Judit, Vecsernyés Miklós, Herczegh Pal
机构信息
Department of Pharmaceutical Chemistry and Research Group for Antibiotics of the Hungarian Academy of Sciences, University of Debrecen, Egyetem tér 1, P.O. Box 70 H-4010 Debrecen, Hungary.
出版信息
J Med Chem. 2006 Sep 7;49(18):5626-30. doi: 10.1021/jm060471h.
A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-d-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.
报道了一种由α,β-不饱和硫苯基酯简单合成1,2-二硫杂环戊烷-3-酮的方法。将链黑菌素具有生物活性的1,2-二硫杂环戊烷-3-酮-1-氧化物部分引入醛基-d-阿拉伯糖11、尿苷衍生物16和脱氧胸苷21中得以实现。还合成了带有碳-碳三键的链黑菌素的扩展生物活性部分。所有这些链黑菌素类似物均对HeLa3肿瘤细胞表现出细胞毒性活性。有趣的是，含亲脂性硅烷基的衍生物被证明比亲水性对应物更具活性。
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