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Synthesis, characterization and pharmacological evaluation of some new 1,3,4-oxadiazole derivatives bearing 3-chloro-2-fluoro phenyl moiety

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Abstract

A new series of 2-(3-chloro-2-fluorophenyl)-5-aryl-1,3,4-oxadiazole (3a–j) and 2-(aryl sulfanyl)-5-(3-chloro-2-fluorophenyl)-1,3,4-oxadiazole (5a–e) were synthesized via a multistep reaction from 3-chloro-2-fluoro benzoic acid. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis. They were also screened for their in vivo anti-convulsant and anti-inflammatory activities. Some of them exhibited significant biological activities and were well supported by in silico molecular docking studies for the inhibition of cyclooxygenase-2 (PDB ID: 1CX2) and voltage-gated sodium channels (PDB ID: 4F4L) comparable with the standard drugs. Thus, they were believed to be good inhibitors of cyclooxygenase-2 (PDB ID: 1CX2) and voltage-gated sodium channels (PDB ID: 4F4L).

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Acknowledgments

One of the authors, Manjunatha Bhat, is grateful to the management of SeQuent Scientific Ltd., New Mangalore, India, for encouraging research work. Manjunatha Bhat is also grateful to Prof. A. Srikrishna, Department of Organic Chemistry, IISc, Bangalore, for providing 1H NMR and 13C NMR spectral facilities. We are also grateful to Dayanandsagar College of Pharmacy, Bangalore, for providing sincere help for the biological activity studies. The authors are also grateful to the Chairman, Dept. of Chemistry, Mangalore University.

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Authors and Affiliations

  1. Department of Post Graduate Studies and Research in Chemistry, Mangalore University, Mangalagangothri, Mangalore, Karnataka, 574199, India

    Manjunatha Bhat, G. K. Nagaraja & Reshma Kayarmar

  2. SeQuent Scientific Limited, No: 120 A&B, Industrial Area, Baikampady, New Mangalore, Karnataka, 575011, India

    Manjunatha Bhat & Reshma Kayarmar

  3. Dayanand Sagar College of Pharmacy, Bangalore, Karnataka, India

    S. V. Raghavendra

  4. Department of PG Studies and Research in Biotechnology and Bioinformatics, Kuvempu University, Jnanasahyadri, Shankaraghatta, Karnataka, 577451, India

    K. P. Rajesh & H. Manjunatha

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  1. Manjunatha Bhat
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  2. G. K. Nagaraja
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  3. Reshma Kayarmar
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  4. S. V. Raghavendra
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  5. K. P. Rajesh
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  6. H. Manjunatha
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Correspondence to G. K. Nagaraja.

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Bhat, M., Nagaraja, G.K., Kayarmar, R. et al. Synthesis, characterization and pharmacological evaluation of some new 1,3,4-oxadiazole derivatives bearing 3-chloro-2-fluoro phenyl moiety. Res Chem Intermed 42, 7771–7792 (2016). https://doi.org/10.1007/s11164-016-2561-4

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