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Synthesis and antimicrobial activities of 2-azetidinyl-4-quinazolinone derivatives of diclofenac analogue

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Abstract

A new class of 2-azetidinyl-4-quinazolinones 6a–k was synthesized by multi-step process, starting from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetic acid 1. Acid 1 was easily converted to acid chloride 2, which on cyclization reaction with 5-bromo anthranilic acid yielded benzoxazinone 3. The condensation reaction of 3 with benzene-1,4-diamine afforded 4-quinazolinone 4. Finally the title compound 6a–k was synthesized from 4-quinazolinone 4 by Schiff base formation 5a–k with aromatic aldehyde and then cyclization reaction with chloroacetylchloride. The in vitro antimicrobial activity of compounds 5a–k and 6a–k were tested. These compounds showed pronounced antimicrobial activity when 4-Cl and 4-OCH 3 groups were present.

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Acknowledgments

The authors wish to place their thanks to Professor and Head, Department of Chemistry, VNSGU, Surat. Thanks to SAIF, Punjab University, Chandigarh, for spectral analysis.

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  1. Department of Chemistry, Veer Narmad South Gujarat University, Surat, 395 007, Gujarat, India

    Navin B. Patel & Jaymin C. Patel

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  1. Navin B. Patel
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  2. Jaymin C. Patel
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Correspondence to Navin B. Patel.

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Patel, N.B., Patel, J.C. Synthesis and antimicrobial activities of 2-azetidinyl-4-quinazolinone derivatives of diclofenac analogue. Med Chem Res 20, 511–521 (2011). https://doi.org/10.1007/s00044-010-9345-y

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  • DOI: https://doi.org/10.1007/s00044-010-9345-y

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