通过施陶丁格反应进行抗癌β-内酰胺的立体控制合成。

Stereocontrolled synthesis of anticancer beta-lactams via the Staudinger reaction.

作者信息

Banik Bimal K, Banik Indrani, Becker Frederick F

机构信息

Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541, USA.

出版信息

Bioorg Med Chem. 2005 Jun 1;13(11):3611-22. doi: 10.1016/j.bmc.2005.03.044.

DOI:10.1016/j.bmc.2005.03.044

PMID:15862989

Abstract

Stereocontrolled synthesis of novel beta-lactams using polyaromatic imines following the Staudinger reaction has been accomplished. The effects of domestic microwave irradiation on this type of reaction have been investigated. Formation of trans-beta-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride (equivalent) with imines in the presence of triethylamine. A donor-acceptor complex pathway is believed to be involved in the formation of cis-beta-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the resulting beta-lactams. SAR has identified beta-lactams with anticancer activity. The presence of an acetoxy group has proven obligatory for their anticancer activity.

摘要

通过施陶丁格反应，利用多芳族亚胺完成了新型β-内酰胺的立体控制合成。研究了家用微波辐射对这类反应的影响。通过在三乙胺存在下，酰氯（当量）与亚胺反应过程中形成的烯醇化物的异构化，解释了反式β-内酰胺的形成。供体-受体络合物途径被认为参与了顺式β-内酰胺的形成。已发现周位氢在控制所得β-内酰胺的立体化学方面具有显著作用。构效关系已确定具有抗癌活性的β-内酰胺。已证明乙酰氧基的存在对其抗癌活性至关重要。