Synthesis of novel N-sulfonyl monocyclic beta-lactams as potential antibacterial agents

Aliasghar Jarrahpour; Maaroof Zarei

doi:10.3390/11010049

Synthesis of novel N-sulfonyl monocyclic beta-lactams as potential antibacterial agents

Molecules. 2006 Jan 31;11(1):49-58. doi: 10.3390/11010049.

Authors

Aliasghar Jarrahpour¹, Maaroof Zarei

Affiliation

¹ Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran. jarrah@susc.ac.ir

Abstract

New cis monocyclic beta-lactams were synthesized by [2+2] Staudinger cycloaddition reactions of the imine (3,4-dimethoxybenzylidene)-(4-methoxyphenyl)-amine and ketenes derived from different acyl chlorides and Et3N. These monocyclic beta-lactams were then cleaved by ceric ammonium nitrate (CAN) to give NH-monocyclic beta-lactams, which in turn were converted to N-sulfonyl monocyclic beta-lactams by treatment with four different sulfonyl chlorides in the presence of Et3N and 4,4-dimethyl-aminopyridine (DMAP).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Models, Biological
Molecular Conformation
Monobactams / chemical synthesis*
Monobactams / chemistry

Substances

Anti-Bacterial Agents
Monobactams