Abstract
A new class of 4-arylhydrazono-1-benzothiazolyl-3-methylpyrazolin-5-ones (3a–j) and 4-arylazo-1-benzothiazolyl-3,5-dimethylpyrazoles (4a–j) were designed as pharmacophore hybrids between pyrazolinone/pyrazole and benzothiazole moiety. The target molecules were efficiently synthesized by the cyclization of various oxobutyrates/pentane-2,4-dione derivatives with 6-chloro-2-hydrazinobenzothiazole in the presence of glacial acetic acid. The compounds were evaluated for their in vitro antimicrobial activity. Preliminary study of the structure–activity relationship revealed that electron-withdrawing groups in phenyl ring had a promising effect on the antimicrobial activity. Also, correlation study has been used to establish the relationships between the antibacterial activity and physicochemical parameter clogP.
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Acknowledgments
The authors wish to express their thanks to University Grant Commission-New Delhi, India for the UGC fellowship and Majeedia Hospital, Hamdard University, New Delhi, India for providing antimicrobial research facilities.
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Amir, M., Javed, S.A. & Zaheen Hassan, M. Synthesis and antimicrobial activity of pyrazolinones and pyrazoles having benzothiazole moiety. Med Chem Res 21, 1261–1270 (2012). https://doi.org/10.1007/s00044-011-9642-0
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DOI: https://doi.org/10.1007/s00044-011-9642-0