Synthesis of New N-Sulfonyl Monocyclic β-Lactams and the Investigation of Their Antibacterial Activities

被引：31

作者：

Jarrahpour, Aliasghar ^{[1
]}

Motamedifar, Mohammad ^{[2
]}

Zarei, Maaroof ^{[1
]}

Mimouni, Mostafa ^{[3
]}

机构：

[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

[2] Shiraz Univ Med Sci, Shiraz Med Sch, Dept Bacteriol & Virol, Shiraz, Iran

[3] Univ Mohammed Premier, Lab Chim Mat, Oujda, Morocco

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2010年 / 185卷 / 02期

关键词：

Antibacterial activity; 2-azetidinones; imines; ketenes; Staudinger reaction; N-sulfonyl; -lactams; USEFUL BUILDING-BLOCKS; SOLID-PHASE SYNTHESIS; PROTEASE CATHEPSIN-K; 3,4-DISUBSTITUTED AZETIDINONES; ANTIMICROBIAL ACTIVITY; SELECTIVE INHIBITORS; ASYMMETRIC-SYNTHESIS; MECHANISM; EFFICIENT; ELASTASE;

D O I：

10.1080/10426500902773161

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New monocyclic -lactams 4-6 were synthesized by a ketene-imine [2+2] cycloaddition reaction. The prepared monocyclic -lactams 4-6 were cleaved by ceric ammonium nitrate (CAN) to give NH--lactams 7-9. The NH--lactams were converted to N-sulfonyl -lactams 10-21 by treatment with four different sulfonyl chlorides in the presence of Et3N and 4-N,N-dimethylaminopyridine (DMAP). Some of these monocyclic -lactams were active against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

引用

页码：287 / 297

页数：11

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