Synthesis and biological evaluation of some novel diastereoselective benzothiazole β-lactam conjugates
Abstract Highly diastereoselective synthesis of some novel benzothiazole-substituted β-lactam hybrids was achieved starting from (benzo[ d ]thiazol-2-yl)phenol as an available precursor. This is the first time (benzo[ d ]thiazol-2-yl)phenoxyacetic acid has been used as ketene source in synthesizing monocyclic 2-azetidinones. These compounds were evaluated for their antimicrobial activities against a large panel of Gram-positive and Gram-negative bacterial strains and moderate activities were encountered. Antimalarial data revealed that adding methoxyphenyl or ethoxyphenyl group on the β–lactam ring makes compounds that are more potent. Moreover, hemolytic activity and mammalian cell toxicity survey of the compounds showed their potential as a medicine. Highlights A new series of cis benzothiazole β-lactam conjugates have been synthesized. Good activities against chloroquine resistant P. falciparum K1 strain. Less cytotoxicity effect on hepatocellular carcinoma cell line (HepG2). Red blood cells stability as hemolysis assay exhibited excellent results. A single crystal X-ray structure of 5n has been determined. Graphical abstract [DISPLAY OMISSION]
β-Lactam . Benzothiazole . Antimicrobial . Antimalarial . Staudinger reaction . Mammalian cell toxicity . AWEPBXMJYNMWLO-RRPNLBNLSA-N . XTXRPHWFUAIUCP-RRPNLBNLSA-N . KIIUICHYKBLOPA-OIDHKYIRSA-N . LWJMTMVCGJWJLQ-FAWOHUEESA-N . UNJFXXCHHNOQMJ-RRPNLBNLSA-N . VFXQOZCBIUFTJW-RRPNLBNLSA-N . TWSJLWKNAUXJCT-WUFINQPMSA-N . FIIGOEKKBIIFSC-IOWSJCHKSA-N . LCNVSNYMGOIXTA-RRPNLBNLSA-N . YYUZOMMGLLXURW-RRPNLBNLSA-N . LHNBYDZGUNHWGH-LMSSTIIKSA-N . AJEHOWKEUWWAAJ-WUFINQPMSA-N . ABAXCWPRJWJICS-RRPNLBNLSA-N . YKFBERQWADEGCU-XZWHSSHBSA-N . SCXWGOGBADRNEV-RRPNLBNLSA-N . MSHIECGZYNJLBL-URLMMPGGSA-N.
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