含多芳族亚胺的β-内酰胺的立体选择性合成：通向新型抗癌剂之路。

Stereoselective synthesis of beta-lactams with polyaromatic imines: entry to new and novel anticancer agents.

作者信息

Banik Indrani, Becker Frederick F, Banik Bimal K

机构信息

The University of Texas M. D. Anderson Cancer Center, Department of Molecular Pathology, Box 89, 1515 Holcombe Boulevard, Houston, Texas 77030, USA.

出版信息

J Med Chem. 2003 Jan 2;46(1):12-5. doi: 10.1021/jm0255825.

DOI:10.1021/jm0255825

PMID:12502355

Abstract

We present herein stereoselective synthesis of novel beta-lactams using polyaromatic imines following the Staudinger reaction. Consistent mechanisms for these results have been advanced. As a measure of cytotoxicity, some of these compounds have been assayed against nine human cancer cell lines. Structure-activity study has revealed that 1-N-chrysenyl and 1-N-phenanthrenyl 3-acetoxy-4-aryl-2-azetidinones have potent anticancer activity. The presence of the acetoxy group at C(3) of the beta-lactams has proven to be obligatory for their anticancer activity.

摘要

我们在此展示了利用多芳族亚胺通过施陶丁格反应进行新型β-内酰胺的立体选择性合成。针对这些结果提出了一致的机理。作为细胞毒性的一种衡量标准，已对其中一些化合物针对九种人类癌细胞系进行了测定。构效关系研究表明，1-N- Chryseryl和1-N-菲基3-乙酰氧基-4-芳基-2-氮杂环丁酮具有强大的抗癌活性。事实证明，β-内酰胺C(3)位上乙酰氧基的存在对其抗癌活性至关重要。