Novel synthesis of β-lactams and their biological evaluation

被引:0
作者
Banik, Bimal K. [1 ]
机构
[1] Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78539 USA
基金
美国国家卫生研究院;
关键词
beta-Lactams; Staudinger reaction; stereochemistry; mechanism of action; microwave-induced reactions; glycosylation; heterocycles; anticancer agents; POLYCYCLIC AROMATIC-COMPOUNDS; CATALYTIC TRANSFER HYDROGENOLYSIS; INDUCED REDUCTIVE DIMERIZATION; ORGANIC-REACTION ENHANCEMENT; ONE-POT SYNTHESIS; ALPHA-AMINO; STEREOSPECIFIC GLYCOSYLATION; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AMMONIUM FORMATE;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Stereoselective synthesis of racemic and optically active novel beta-lactams using Staudinger cycloaddition reaction with imines and ketenes has been achieved. Microwave induced-reactions have been performed for the preparation of these types of beta-lactams and products derived from them. The formation of trans-beta-lactams has been rationalized via isomerization of the enolates formed between the reactions of acid chloride (equivalent) with imines in the presence of a tertiary base. A donor-acceptor complex formation has been found to be the intermediate occurred in the formation of cis-beta-lactams. A peri hydrogen in the aromatic rings has been proved to be crucial in controlling the isomer distribution of the products. Glycosylation reaction has been performed to prepare a few intermdeaites that are useful for anticancer agents. Cell-growth inhibition study has identified a few beta-lactams that demonstrates anticancer activity. Microwave-induced reactions have been conducted for the synthesis of diverse heterocycles using beta-lactams as the starting compounds.
引用
收藏
页码:1837 / 1860
页数:24
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