synthesis of novel n-sulfonyl monocyclic β-lactams as potential antibacterial agents合成新型n-sulfonyl单环β-lactams作为潜在的抗菌药物.pdfVIP

Molecules 2006, 11, 49-58 molecules ISSN 1420-3049 Synthesis of Novel N-Sulfonyl Monocyclic β-Lactams as Potential Antibacterial Agents Aliasghar Jarrahpour * and Maaroof Zarei Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran. Tel.: (+98) 711 2284822; Fax: (+98) 711 2280926; * Author to whom correspondence should be addressed; e-mail: jarrah@chem.susc.ac.ir or aliasghar6683@ Received: 9 March 2005 / in revised form: 12 December 2005 / Accepted: 14 December 2005 Published: 31 January 2006 Abstract— New cis monocyclic β-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 β-lactams were then cleaved by ceric ammonium nitrate (CAN) to give NH-monocyclic β-lactams, which in turn were converted to N-sulfonyl monocyclic β-lactams by treatment with four different sulfonyl chlorides in the presence of Et3N and 4,4-dimethyl- aminopyridine (DMAP). Keywords: 2-Azetidinones, N-Sulfonyl β-lactams, Ketene, Imine, CAN, DMAP Introduction Even more than 70 years after the discovery of penicillin, β-lactam antibiotics remain as one of the most important contributions of science to Humanity [1]. The β-lactam skeleton is the common structural element of the widely used penicillins, cephalosporins, thienamycine, nocardicins, aztreonam and carumonam [2]. The first member of this class of compo