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Asymmetric Synthesis and Antimicrobial Activity of Some New Mono and Bicyclic β-Lactams
Chemistry Department, College of Sciences, Shiraz University, Shiraz 71454, Iran
Institute of Standards and Industrial Research of Iran, Shiraz 71447, Iran
* Author to whom correspondence should be addressed.
Received: 24 September 2004; Accepted: 31 August 2004 / Published: 30 November 2004
Abstract: Reaction of the amino acid D-phenylalanine ethyl ester (4) with cinnamaldehyde gave chiral Schiff base 5, which underwent an asymmetric Staudinger [2+2] cycloaddition reaction with phthalimidoacetyl chloride to give the monocyclic β-lactam 6 as a single stereoisomer. Ozonolysis of 6 followed by reduction with lithium aluminum tri(tert-butoxy) hydride afforded the hydroxymethyl β-lactam 8. Treatment of 8 with methansulfonyl chloride gave the mesylated monocyclic β-lactam 9, which was converted to the bicyclic β-lactam 10 upon treatment with 1,8-diazabicyclo[5,4.0] undec- 7-ene (DBU). Deprotection of the phthalimido group in β-lactams 6 and 10 by methylhydrazine and subsequent acylation of the free amino β-lactams with different acyl chlorides in the presence of pyridine afforded mono and bicyclic β-lactams 14a-d and 15a-d respectively. The compounds prepared were tested against Escherichia coli, Staphilococcus citrus, Klebsiella pneumanie and Bacillus subtillis. Some of these compounds showed potential antimicrobial activities.
Keywords: D-Phenylalanine; asymmetric induction; chiral Schiff base; DBU; antimicrobial
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Jarrahpour, A.A.; Shekarriz, M.; Taslimi, A. Asymmetric Synthesis and Antimicrobial Activity of Some New Mono and Bicyclic β-Lactams. Molecules 2004, 9, 939-948.
Jarrahpour AA, Shekarriz M, Taslimi A. Asymmetric Synthesis and Antimicrobial Activity of Some New Mono and Bicyclic β-Lactams. Molecules. 2004; 9(11):939-948.
Jarrahpour, A. A.; Shekarriz, M.; Taslimi, A. 2004. "Asymmetric Synthesis and Antimicrobial Activity of Some New Mono and Bicyclic β-Lactams." Molecules 9, no. 11: 939-948.