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Efficient synthesis, anticonvulsant and muscle relaxant activities of new 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6-phenyl-4,5-dihydropyridazin-3(2H)-one derivatives

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Abstract

A series of 2-(2-(3-(4-chlorophenyl)-6-oxo-5,6-dihydropyridazin-1(4H)yl)acetyl)hydrazine carbothioamide and 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6-(4-chlorophenyl)-4,5-dihydropyridazin-3(2H)-one derivatives were synthesized, characterized, and evaluated for anticonvulsant activity and muscle relaxant activity. The synthesized compounds 5d (82.75 %) and 5e (85.44 %) showed promising anticonvulsant activity by protection against tonic hind limb extensor phase in maximal electroshock model (MES) at (50 mg/kg) compared to standard drug phenytoin and also compounds 5d (82.75 %), and 5e (85.44 %) showed significant anticonvulsant activity by protection against pentylenetetrazole-induced generalized convulsions in pentylenetetrazole model (PTZ) at (100 mg/kg) compared to standard drug diazepam. On the other hand, compound 5e showed significant muscle relaxant activity (84.57 %) by rotarod and traction test model comparing with diazepam as a standard drug.

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Acknowledgments

The authors are thankful to the Director, SAIF, Punjab University, Chandigarh for IR, 1H NMR, 13C NMR, and Mass spectroscopy, Authors are also thankful to the Director and Head of the department, Institute of pharmacy, Bundelkhand University, Jhansi for providing facilities to conduct the research work and Mrs. Shalini pathak, department of pharmacology, for her support during the pharmacological screening.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Institute of Pharmacy, Bundelkhand University, Jhansi, India

    Bhawna Sharma

  2. Department of Pharmaceutical Sciences, Faculty of Health Sciences, Sam Higginbottom Institute of Agriculture, Technology and Sciences, Allahabad, 211007, India

    Amita Verma

  3. Department of Pharmaceutics, Bundelkhand University, Jhansi, India

    Upendra Kumar Sharma

  4. Department of Pharmaceutics, Institute of Pharmacy, Bundelkhand University, Jhansi, India

    Sunil Prajapati

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  1. Bhawna Sharma
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  2. Amita Verma
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  3. Upendra Kumar Sharma
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  4. Sunil Prajapati
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Correspondence to Bhawna Sharma.

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Sharma, B., Verma, A., Sharma, U.K. et al. Efficient synthesis, anticonvulsant and muscle relaxant activities of new 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6-phenyl-4,5-dihydropyridazin-3(2H)-one derivatives. Med Chem Res 23, 146–157 (2014). https://doi.org/10.1007/s00044-013-0618-0

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