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Microwave-assisted synthesis and anticonvulsant activity of 5,6-bisaryl-1,2,4-triazine-3-thiol derivatives

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Abstract

A series of 5,6-bisaryl-1,2,4-triazine-3-thiol derivatives were synthesized through microwave-promoted chemistry by condensation of the aromatic 1,2-diketones and thiosemicarbazide in a mixed green solvent. Subsequently, S-alkylation of 1,2,4-triazine-3-thiols afforded S-substituted derivatives. The anticonvulsant activity of the synthesized compounds was evaluated in vivo by electroshock and pentylenetetrazole (PTZ)-induced seizures tests. Among them, compound 4a bearing 4-pyridylmethylthio moiety on the triazine ring showed the highest protection in both electroshock and PTZ-induced seizures tests. Compound 4a showed no sign of neurotoxicity at the dose of 100 mg/kg in both rotarod and chimney tests.

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Acknowledgments

We gratefully acknowledge the financial support from the Research Council of Mazandaran University of Medical Sciences, Sari, Iran.

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Authors and Affiliations

  1. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Mazandaran University of Medical Sciences, Sari, Iran

    Hamid Irannejad, Saeed Emami & Roja Qobadi Ghadikolaei

  2. Department of Pharmacology and Toxicology, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran

    Nima Naderi

  3. Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Alireza Foroumadi

  4. Faculty of Medicine, Shahid Beheshti University of Medical Sciences, Tehran, Iran

    Tina Zafari & Ali Mazar-Atabaki

  5. Student Research Committee, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran

    Sakineh Dadashpour

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  1. Hamid Irannejad
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  2. Nima Naderi
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Correspondence to Hamid Irannejad.

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Irannejad, H., Naderi, N., Emami, S. et al. Microwave-assisted synthesis and anticonvulsant activity of 5,6-bisaryl-1,2,4-triazine-3-thiol derivatives. Med Chem Res 23, 2503–2514 (2014). https://doi.org/10.1007/s00044-013-0843-6

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  • DOI: https://doi.org/10.1007/s00044-013-0843-6

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