Synthesis and biological evaluation of some novel diastereoselective benzothiazole β-lactam conjugates

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-...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2018-01, Vol.143 (C), p.283-291
Main Authors: Alborz, Maryam, Jarrahpour, Aliasghar, Pournejati, Roya, Karbalaei-Heidari, Hamid Reza, Sinou, Véronique, Latour, Christine, Brunel, Jean Michel, Sharghi, Hashem, Aberi, Mahdi, Turos, Edward, Wojtas, Lukasz
Format: Article
Language:English
Subjects:
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AJEHOWKEUWWAAJ-WUFINQPMSA-N
Antimalarial
Antimicrobial
AWEPBXMJYNMWLO-RRPNLBNLSA-N
Benzothiazole
FIIGOEKKBIIFSC-IOWSJCHKSA-N
KIIUICHYKBLOPA-OIDHKYIRSA-N
LCNVSNYMGOIXTA-RRPNLBNLSA-N
LHNBYDZGUNHWGH-LMSSTIIKSA-N
Life Sciences
LWJMTMVCGJWJLQ-FAWOHUEESA-N
Mammalian cell toxicity
MSHIECGZYNJLBL-URLMMPGGSA-N
SCXWGOGBADRNEV-RRPNLBNLSA-N
Staudinger reaction
TWSJLWKNAUXJCT-WUFINQPMSA-N
UNJFXXCHHNOQMJ-RRPNLBNLSA-N
VFXQOZCBIUFTJW-RRPNLBNLSA-N
XTXRPHWFUAIUCP-RRPNLBNLSA-N
YKFBERQWADEGCU-XZWHSSHBSA-N
YYUZOMMGLLXURW-RRPNLBNLSA-N
β-Lactam
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Summary: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. [Display omitted] •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.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2017.11.053