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Design, synthesis and biological evaluation of some novel benzylidene-2-(4-phenylthiazol-2-yl) hydrazines as potential anti-inflammatory agents

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Abstract

A series of substituted benzylidene-2-(4-phenylthiazol-2-yl) hydrazines (2a–q) have been synthesized, characterized and evaluated for their anti-inflammatory activity by carrageenin-induced hind paw edema (acute inflammation) and cotton pellet granuloma (chronic inflammation) methods in rats. In carrageenin-induced hind paw edema method, compounds 2a, 2b, 2c, 2d, 2h, 2k and 2p at a dose of 20 mg kg−1 body weight, p.o. showed excellent inhibitions (51.80–86.74 %) in between 1 and 4 h. Similarly, in cotton pellet granuloma method, compounds 2a, 2b, 2c, 2d, 2h, 2k and 2p at a dose of 20 mg kg−1 body weight, p.o. inhibited the granuloma formation (71.71–90.19 % inhibition) which was comparable to that of standard drug, ibuprofen (90.36 % inhibition of paw volume at 3 h and 94.02 % inhibition of granuloma formation). Structure activity relationship studies showed excellent activity of the compounds containing electron withdrawing group (fluoro, chloro, bromo or nitro) in phenyl ring at C2 and/or C4 position of thiazole ring.

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Acknowledgments

The authors are grateful to the Head, Department of Chemistry, Faculty of Science, Banaras Hindu University (BHU), Varanasi, India for 1H and 13C NMR spectrometry, Indian Institute of Chemical Technology (IICT), Hyderabad for mass spectrometry. S.K. Bharti is grateful to University Grants Commission (UGC), New Delhi for the award of senior research fellowship.

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  1. Department of Medicinal Chemistry, Institute of Pharmaceutical Sciences, Guru Ghasidas Vishwavidyalaya (G.G.V.), Bilaspur, 495009, India

    Sanjay Kumar Bharti

  2. Department of Pharmaceutics, Indian Institute of Technology (Banaras Hindu University), Varanasi, 221005, India

    Sushil Kumar Singh

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  1. Sanjay Kumar Bharti
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Correspondence to Sanjay Kumar Bharti.

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Bharti, S.K., Singh, S.K. Design, synthesis and biological evaluation of some novel benzylidene-2-(4-phenylthiazol-2-yl) hydrazines as potential anti-inflammatory agents. Med Chem Res 23, 1004–1015 (2014). https://doi.org/10.1007/s00044-013-0708-z

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