Skip to main content
Log in

Synthesis and anticonvulsant activity of some potent 5,6-bis aryl 1,2,4-triazines

  • Published:
Journal of Zhejiang University SCIENCE B Aims and scope Submit manuscript

Abstract

In the present research, a series of 5,6-bis aryl 1,2,4-triazines 5a5f were synthesized by condensation of various benzils 4a4f with aminoguanidine bicarbonate and were screened in vivo, for their anticonvulsant and neurotoxicity studies. Compounds 5a, 5b and 5d were found to be potent molecules of this series, when compared with the reference drugs phenytoin sodium, diazepam and lamotrigine. The structures of these compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopic data.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Chang, B.S., Lowenstein, D.H., 2003. Mechanisms of disease: epilepsy. N. Eng. J. Med., 349(13):1257–1262. [doi:10.1056/NEJMra022308]

    Article  Google Scholar 

  • Danny, D.S., René, H.L., Jill, L.S., Alan, V., 1992. Comparative anticonvulsant potency and pharmacokinetics of (+)-and (−)-enantiomers of stiripentol. Epilepsy Res., 1(11): 29–36.

    Google Scholar 

  • Dimmock, J.R., Sidhu, K.K., Tumber, D.F., 1995a. Some aryl semicarbazones possessing anticonvulsant activitie. Eur. J. Med. Chem., 30(4):287–301. [doi:10.1016/0223-5234(96)88237-7]

    Article  CAS  Google Scholar 

  • Dimmock, J.R., Vashishtha, S.C., Stables, J.P., 1995b. Evaluation of the semicarbazones, thiosemicarbazones and bis-carbohydrazones of some aryl alicycylic ketones for anticonvulsant and other biological propertie. Eur. J. Med. Chem., 30(4):303–314. [doi:10.1016/0223-5234(96)88238-9]

    Article  CAS  Google Scholar 

  • Duncan, J.S., 2002. The promise of new antiepileptic drugs. Br. J. Clin. Pharmacol., 53(2):123–131. [doi:10.1046/j.0306-5251.2001.01540.x]

    Article  PubMed  CAS  Google Scholar 

  • Erickson, J.G., 1952. 3-Amino-as-triazines. J. Am. Chem. Soc., 74(18):4706. [doi:10.1021/ja01138a506]

    Article  CAS  Google Scholar 

  • Fisher, R.S., 1989. Animal models of the epilepsies. Brain Research Reviews, 14(3):245–278. [doi:10.1016/0165-0173(89)90003-9]

    Article  PubMed  CAS  Google Scholar 

  • Grundmann, C., Kreutzberger, A., 1954. 1,3,5-Triazine. J. Am. Chem. Soc., 76(2):632–633. [doi:10.1021/ja01631a107]

    Article  CAS  Google Scholar 

  • Hosford, D.A., Wang, Y., 1997. Utility of the lethargic (lh/lh) mouse model of absence seizures in predicting the effects of lamotrigine, vigabatrin, tiagabine, gabapentin, and topiramate against human absence seizures. Epilepsia, 38(4):408–414. [doi:10.1111/j.1528-1157.1997.tb01729.x]

    Article  PubMed  CAS  Google Scholar 

  • Kubicki, M., Codding, P.W., 2001. Hydrogen bonding patterns in 3,5-diamino-6-aryl triazines. Journal of Molecular Structure, 570(1–3):53–60. [doi:10.1016/S0022-2860(01)00477-X]

    Article  CAS  Google Scholar 

  • McNamara, J.O., 2001. Drugs Effective in the Therapy of the Epliepsies. In: Hardman, L.G., Limbird, L.E. (Eds.), Goodman and Gilman’s the Pharmacological Basis of Therapeutics. McGraw Hill, New York, p.521–547.

    Google Scholar 

  • Pandeya, S.N., Yogeswari, P., Stables, J.P., 2000. Synthesis and anticonvulsant activity of 4-bromophenyl substituted aryl semicarbazones. Eur. J. Med. Chem., 35(10):879–886. [doi:10.1016/S0223-5234(00)01169-7]

    Article  PubMed  CAS  Google Scholar 

  • Pastalos, P.N., 1999. Synthesis of some oxime ether derivatives of 1-(2-naphthyl)-2-(1,2,4-triazol-1-yl)ethanone and their anticonvulsant and antimicrobial activities. Curr. Opin. CPNS Invest. Drugs, 1(64):549–555.

    Google Scholar 

  • Petroff, O.A., Rothman, D.L., Behar, K.L., Mattson, R.H., 1995. Initial observations on effect of vigabatrin on in vivo 1H spectroscopic measurements of γ-aminobutyric acid, glutamate, and glutamine in human brain. Epilepsia, 36(5):457–464. [doi:10.1111/j.1528-1157.1995.tb00486.x]

    Article  PubMed  CAS  Google Scholar 

  • Porsolt, R.D., Anton, G., Blavet, N., Jalfre, M., 1978. Behavioural despair in rats: a new model sensitive to antidepressant treatments. Eur. J. Pharmacol., 47(4):379–391. [doi:10.1016/0014-2999(78)90118-8]

    Article  PubMed  CAS  Google Scholar 

  • Richard, W.A., Peter, B.R., Theodre, J.F., 1972. Antimalarial activities of some 3,5-diamino-as-triazine derivatives. J. Med. Chem., 15(4):859–871.

    Google Scholar 

  • Sander, J.W.A.S., 1993. Some aspects of prognosis in the epilepsies: a review. Epilepsia, 34(6):1007–1016. [doi:10.1111/j.1528-1157.1993.tb02126.x]

    Article  PubMed  CAS  Google Scholar 

  • Sawyer, D.A., Copp, F.C., 1992. Synthesis of novel triazoles as potent anticonvulsants. Chem. Abstr., 108:1125.

    Google Scholar 

  • Smith, Q.E., 1960. Pharmacological Screening Tests Progress in Medicinal Chemistry. 1: Butterworths. London, p.1–33.

    Google Scholar 

  • Stephani, U., 1989. The natural history of myoclonic astatic epilepsy the natural history of myoclonic astatic epilepsy. Epilepsia, 47(Suppl. 1):S53–S55.

    Google Scholar 

  • Taylor, C.P., 1996. Voltage-gated Na+ channels as targets for anticonvulsant, analgesic and neuroprotective drugs. Curr. Pharm. Des., 2(4):375–379.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mallikarjuna, B.P., Suresh Kumar, G.V., Sastry, B.S. et al. Synthesis and anticonvulsant activity of some potent 5,6-bis aryl 1,2,4-triazines. J. Zhejiang Univ. - Sci. B 8, 526–532 (2007). https://doi.org/10.1631/jzus.2007.B0526

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1631/jzus.2007.B0526

Key words

CLC number

Navigation