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One pot synthesis of thiazolo[2,3-b]dihydropyrimidinone possessing pyrazole moiety and evaluation of their anti-inflammatory and antimicrobial activities

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Abstract

A series of pyrazole integrated thiazolo[2,3-b]dihydropyrimidinone derivatives were synthesized as dual anti-inflammatory and antimicrobial agents. Among the compounds studied, 3-fluoro-4-methylphenyl analogues (3a, 3e, and 3i) are considered to be promising leads for novel anti-inflammatory agents compared with the standard drug. The superior antimicrobial property of the compounds 3a, 3b, and 3d indicates that 3-(3,4-dichlorophenyl)-1-phenyl-1H-pyrazole substitution is a favourable site for high activity. Molecular docking studies were carried out in order to predict the hypothetical binding mode of these compounds to the COX-2 isoenzyme. The results of the present study suggest that 1,3-diaryl pyrazole substitution on thiazolo[2,3-b]dihydropyrimidinone derivatives might potentially constitute a novel class of anti-inflammatory agents with antimicrobial property and could be an interesting approach for the design of new selective COX-2 inhibitory agents.

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Acknowledgements

The authors gratefully acknowledge the UGC, SAP, and DST-PURSE for the financial assistance. We are grateful to IISC Bangalore, Mysore University and USIC Mangalore University for providing the spectral analysis. We gratefully acknowledge Prasanna Shama, N.G.S.M. Institute of Pharmaceutical Sciences, Paneer Deralakatte, Mangalore, for anti-inflammatory activity and Guru Basavarajaswamy from Acharya & B.M. Reddy College of Pharmacy for molecular docking study. Also, thankful to Poornachandra Rao K and Sreenivasa MY from the Department of Microbiology Manasagangothri, Mysore University, Mysore, for antimicrobial study.

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Authors and Affiliations

  1. Department of Studies in Chemistry, Mangalore University, Mangalagangotri, 574199, Karnataka, India

    Shivapura Viveka,  Dinesha & Gundibasappa Karikannar Nagaraja

  2. Department of Pharmacology, N.G.S.M. Institute of Pharmaceutical Sciences, Paneer Deralakatte, Mangalore, 574160, Karnataka, India

    Prasanna Shama

  3. Acharya & B.M. Reddy College of Pharmacy, Soldevanahalli, Chikkabanavara Post, Bangalore, 560 090, Karnataka, India

    Guru Basavarajaswamy

  4. Department of Microbiology, Manasagangothri, Mysore University, Mysore, 570006, Karnataka, India

    K. Poornachandra Rao & Marikunte Yanjarappa Sreenivasa

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  1. Shivapura Viveka
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Correspondence to Gundibasappa Karikannar Nagaraja.

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Viveka, S., Dinesha, Nagaraja, G.K. et al. One pot synthesis of thiazolo[2,3-b]dihydropyrimidinone possessing pyrazole moiety and evaluation of their anti-inflammatory and antimicrobial activities. Med Chem Res 27, 171–185 (2018). https://doi.org/10.1007/s00044-017-2058-8

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  • DOI: https://doi.org/10.1007/s00044-017-2058-8

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