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Review Article

Recent developments on triazole nucleus in anticonvulsant compounds: a review

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Pages 453-478 | Received 14 Nov 2017, Accepted 27 Dec 2017, Published online: 31 Jan 2018

References

  • Chang BS, Lowenstein DH. Epilepsy. N Engl J Med 2003;349:1257–66.
  • Singh SP, Sankaraneni R, Antony AR. Evidence-based guidelines for the management of epilepsy. Neurol India 2017;65:S6–S11.
  • Terrone G, Pauletti A, Pascente R, et al. Preventing epileptogenesis: a realistic goal? Pharmacol Res 2016;110:96–100.
  • Stephen JM, Hammer GD, eds. Pathophysiology of disease: an introduction to clinical medicine. 6th ed. New York: McGraw-Hill; 2010.
  • Goldberg EM, Coulter DA. Mechanisms of epileptogenesis: a convergence on neural circuit dysfunction. Nat Rev Neurosci 2013;14:337–49.
  • Longo DL. “369 Seizures and Epilepsy”. Harrison’s principles of internal medicine. 18th ed. New York: McGraw-Hill; 2012.
  • Pandolfo M. Genetics of epilepsy. Semin Neurol 2011;31:506–18.
  • Weaver DF. Epileptogenesis, ictogenesis and the design of future antiepileptic drugs. Can J Neurol Sci 2003;30:4–7.
  • Abou-Khalil BW. Comparative monotherapy trials and the clinical treatment of epilepsy. Epilepsy Curr 2007;7:127–9.
  • Privitera M. Current challenges in the management of epilepsy. Am J Manag Care 2011;17(Suppl. 7):S195–S203.
  • Brodie MJ. Antiepileptic drug therapy the story so far. Seizure 2010;19:650–5.
  • Stefan H, Feuerstein TJ. Novel anticonvulsant drugs. Pharmacol Ther 2007;113:165–83.
  • Wyllie E. Wyllie’s treatment of epilepsy: principles and practice. Philadelphia: Lippincott Williams & Wilkins; 2012.
  • Flanagan SR, Zaretsky H, Moroz A. Medical aspects of disability; a handbook for the rehabilitation professional. 4th ed. New York: Springer Publishing Co Inc.; 2010.
  • Kwan P, Brodie MJ. Early identification of refractory epilepsy. N Engl J Med 2000;342:314–9.
  • Kupferberg HJ. Antiepileptic drug development program: a cooperative effort of government and industry. Epilepsia 1989;30:S51–S6.
  • Stables JP, Kupferberg HJ. The NIH Anticonvulsant Drug Development (ADD) Program: preclinical anticonvulsant screening project. London: John Libbey & Company Ltd.; 1997.
  • White HS, Johnson M, Wolf HH, et al. The early identification of anticonvulsant activity: role of the maximal electroshock and subcutaneous pentylenetetrazol seizure models. Ital J Neurol Sci 1995;16:73–7.
  • Sarkisian MR. Overview of the current animal models for human seizure and epileptic disorders. Epilepsy Behav 2001;2:201–16.
  • Loscher W. Critical review of current animal models of seizures and epilepsy used in the discovery and development of new antiepileptic drugs. Seizure 2011;20:359–68.
  • Rothan HA, Amini E, Faraj FL, et al. NMDA receptor antagonism with novel indolyl, 2-(1,1-Dimethyl-1,3-dihydro-benzo[e]indol-2-ylidene)-malonaldehyde, reduces seizures duration in a rat model of epilepsy. Sci Rep 2017;30:45540.
  • Bakas T, Van Nieuwenhuijzen PS, Devenish SO, et al. The direct actions of cannabidiol and 2-arachidonoyl glycerol at GABAA receptors. Pharmacol Res 2017;119:358–70.
  • Ayati A, Emami S, Foroumadi A. The importance of triazole scaffold in the development of anticonvulsant agents. Eur J Med Chem 2016;109:380–92.
  • Zhou CH, Wang Y. Recent researches in triazole compounds as medicinal drugs. Curr Med Chem 2012;19:239–80.
  • Bele DS, Singhvi I. A review on 1,2,4-triazoles. Asian J Biochem Pharm Res 2011;1:88–101.
  • Kharb R, Kharb R, Sharma PC, Yar MS. Pharmacological significance of triazole scaffold. J Enzyme Inhib Med Chem 2011;26:1–21.
  • Nath PS, Ashish P, Rupesh M. Triazole: a potential bioactive agent (synthesis and biological activity). Int J Res Ayurveda Pharm 2011;2:1490–4.
  • Wakale VS, Pattan SR, Tambe V. Therapeutic importance of 1,2,4-triazole: a review. Int J Res Pharm Biomed Sci 2013;4:985–1001.
  • Küçükgüzel SG, Çıkla-Süzgün P. Recent advances bioactive 1,2,4-triazole-3-thiones. Eur J Med Chem 2015;97:830–70.
  • Dheer D, Singh V, Shankar R. Medicinal attributes of 1,2,3-triazoles: current developments. Bioorg Chem 2017;71:30–54.
  • Kumudha D, Reddy RR, Kalavathi T. 1,2,4-triazoles: as biologically important agents. J Pharm Sci Res 2012;3:4562–72.
  • Saini MS, Dwivedi J. Synthesis and biological significances of 1,2,4-triazole and its derivatives: a review. Int J Pharm Sci Res 2013;4:2866–79.
  • Khatak M, Verma PK. Microwave synthesis and pharmacological importance of 1,2,4-triazole derivatives. World J Pharm Pharm Sci 2014;3:388–409.
  • Kamboj VK, Verma PK, Dhanda A, et al. 1,2,4-Triazole derivatives as potential scaffold for anticonvulsant activity. Cent Nerv Syst Agents Med Chem 2015;15:17–22.
  • Emami S, Kebriaeezadeh A, Zamani MJ, et al. Azolylchromans as a novel scaffold for anticonvulsant activity. Bioorg Med Chem Lett 2006;16:1803–6.
  • Kebriaeezadeh A, Emami S, Ebrahimi M, et al. Anticonvulsant and antiepileptogenic effects of azolylchromanones on lithium-pilocarpine induced seizures and pentylenetetrazole-kindling model of epilepsy. Biomed Pharmacother 2008;62:208–11.
  • Calis U, Dalkara S, Ertan M, et al. The significance of the imidazole ring in anticonvulsant activity of (arylalkyl)imidazoles. Arch Pharm (Weinheim) 1988;321:841–6.
  • Karakurt A, Aytemir MD, Stables JP, et al. Synthesis of some oxime ether derivatives of 1-(2-Naphthyl)-2-(1,2,4-triazol-1-yl)ethanone and their anticonvulsant and antimicrobial activities. Arch Pharm Chem Life Sci 2006;339:513–20.
  • Sari S, Karakurt A, Uslu H, et al. New (arylalkyl)azole derivatives showing anticonvulsant effects could have VGSC and/or GABAAR affinity according to molecular modeling studies. Eur J Med Chem 2016;124:407–16.
  • Srivastava SK, Srivastava S, Srivastava SD. Synthesis of new 1,2,4-triazolylmethylthiadiazolylazetidines as antimicrobial, anticonvulsant and antiinflammatory agents. Indian J Chem 2002;41B:2357–63.
  • Lankau HJ, Unverferth K, Grunwald C, et al. New GABA-modulating 1,2,4-oxadiazole derivatives and their anticonvulsant activity. Eur J Med Chem 2007;42:873–9.
  • Ahangar N, Ayati A, Alipour E, et al. 1-[(2-Arylthiazol-4-yl)methyl]azoles as a new class of anticonvulsants: design, synthesis, in vivo screening, and in silico drug-like properties. Chem Biol Drug Des 2011;78:844–52.
  • Tarikogullari AH, Kilic FS, Erol K, et al. Synthesis and anticonvulsant activity of some alkanamide derivatives. Arzneimittelforschung 2010;60:593–8.
  • Liu DC, Zhang HJ, Jin CM, et al. Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticonvulsant agents. Molecules 2016;21:e164.
  • Wang SB, Deng XQ, Song MX, et al. Synthesis and anticonvulsant activity evaluation of some 1-alkoxy-4-(1H-1,2,4-triazol-1-yl)phthalazines. Lett Drug Des Discov 2012;9:409–14.
  • Wang SB, Jin P, Li FN, et al. Synthesis and anticonvulsant activity of novel purine derivatives. Eur J Med Chem 2014;84:574–83.
  • Kane JM, Baron BM, Dudley MW, et al. 2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents. J Med Chem 1990;33:2772–7.
  • Stocks MJ, Cheshire DR, Reynolds R. Efficient and regiospecific one-pot synthesis of substituted 1,2,4-triazoles. Org Lett 2004;6:2969–71.
  • Bartlett RK, Humphrey IR. Transaminations of N,N-dimethylformamide azine. J Chem Soc C 1967;1664–6.
  • Wei CX, Guan LP, Jia JH, et al. Synthesis of 2-substituted-6-(4H-1,2,4-triazol-4-yl)benzo[d]oxazoles as potential anticonvulsant agents. Arch Pharmacal Res 2009;32:23–31.
  • Song MX, Zeng H, Deng XQ, et al. Synthesis and evaluation of anticonvulsant activities of triazole-incorporated benzothiazoles. Lett Drug Des Discov 2014;11:488–94.
  • Deng XQ, Song MX, Zheng Y, et al. Design, synthesis and evaluation of the antidepressant and anticonvulsant activities of triazole-containing quinolinones. Eur J Med Chem 2014;73:217.
  • Tan YD, He XY, Rao BQ, et al. Synthesis and evaluation of the anticonvulsant activities of triazole-containing benzo[d]oxazoles. Chin J Org Chem 2016;36:2449–55.
  • Song MX, Rao BQ, Cheng BB, et al. Design, synthesis and evaluation of the antidepressant and anticonvulsant activities of triazole-containing benzo[d]oxazoles. CNS Neurol Disord Drug Targets 2017;16:187–98.
  • Wang SB, Deng XQ, Zheng Y, et al. Synthesis and anticonvulsant activity evaluation of 8-alkoxy-5-(4H-1,2,4-triazol-4-yl)quinoline derivative. Arch Pharmacal Res 2013;36:32–40.
  • Davood A, Azimidoost L, Shafaroodi H, et al. Docking and synthesis of 2-arylisoindoline-1,3-dione derivatives as anticonvulsant agents. Pharm Chem J 2014;48:175–80.
  • Fhid ONR, Saad SEA, Zeglam TH, et al. Synthesis, characterization and antiepileptic activity of some new N-substituted phthalimide analogs. J Life Sci 2014;4:373–7.
  • Liu CF, Zhang HJ, Quan ZS. Synthesis and anticonvulsant activity of novel 3-(2-(4H-1,2,4-triazol-4-yl)ethyl)-1-alkyl-1H-indole derivatives. Lett Drug Des Discov 2016;13:833–9.
  • Gall M, Hester JB, Jr, Rudzik AD, et al. Synthesis and pharmacology of novel anxiolytic agents derived from 2-[(dialkylamino)methyl-4H-triazol-4-yl]benzophenones and related heterocyclic benzophenones. J Med Chem 1976;19:1057–64.
  • Arora VK, Knaus EE. Synthesis and anticonvulsant activity of 3-[3-[(dimethylamino)methyl]-5-methyl-4H-1,2,4-triazol-4-yl]-4-(o-chlorobenzoyl)pyridine. J Heterocycl Chem 1999;36:201–3.
  • Akbarzadeh T, Tabatabai SA, Khoshnoud MJ, et al. Design and synthesis of 4H-3-(2-phenoxy)phenyl-1,2,4-triazole derivatives as benzodiazepine receptor agonists. Bioorg Med Chem 2003;11:769–73.
  • Almasirad A, Tabatabai SA, Faizi M, et al. Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg Med Chem Lett 2004;14:6057–9.
  • Almasirad A, Vousooghi N, Tabatabai SA, et al. Synthesis, anticonvulsant and muscle relaxant activities of substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole. Acta Chim Slov 2007;54:317–24.
  • Mahdavi M, Akbarzadeh T, Sheibani V, et al. Synthesis of two novel 3-Amino-5-[4-chloro-2-phenoxyphenyl]-4H-1,2,4-triazoles with anticonvulsant activity. Iran J Pharm Res 2010;9:265–9.
  • Bineshmarvasti M, Jalilian AR, Soltaninejada K, et al. Syntheses and anticonvulsant activity of N4-substituted triazolylthiazoles. Daru J Pharm Sci 2003;11:74–8.
  • Modzelewska-banachiewicz B, Banachiewicz J, Chodkowska A, et al. Synthesis and biological activity of new derivatives of 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid. Eur J Med Chem 2004;39:873–7.
  • Chen J, Sun XY, Chai KY, et al. Synthesis and anticonvulsant evaluation of 4-(4-alkoxylphenyl)-3-ethyl-4H-1,2,4-triazoles as open-chain analogues of 7-alkoxyl-4,5-dihydro[1,2,4]triazolo[4,3-a]quinolines. Bioorg Med Chem 2007;15:6775–81.
  • Cui XS, Chen J, Chai KY, et al. Synthesis and anticonvulsant evaluation of 3-substituted-4-(4-hexyloxyphenyl)-4H-1,2,4-triazoles. Med Chem Res 2007;18:49–58.
  • Wei CX, Wu D, Sun ZG, et al. Synthesis of 6-(3-substituted-4H-1,2,4-triazol-4-yl)-2-phenylbenzo[d]oxazoles as potential anticonvulsant agents. Med Chem Res 2010;19:925–35.
  • Sahoo PK, Purohit S, Sahoo P. Synthesis and biological evaluation of some new [1,2,4]triazole derivatives as anticonvulsant agent. J Pharm Res 2011;4:145–7.
  • Khanage SG, Raju SA, Mohite PB, et al. Synthesis and pharmacological evaluation of some new pyrimidine derivatives containing 1,2,4-triazole. Adv Pharm Bull 2012;2:213–22.
  • Saidov NB, Kadamov IM, Georgiyants VA, et al. Planning, synthesis, and pharmacological activity of alkyl derivatives of 3-mercapto-4-phenyl-5-arylaminomethyl-1,2,4-triazole-(4H). Pharm Chem J 2014;47:581–5.
  • Küçükgüzel I, Küçükgüzel SG, Rollas S, et al. Synthesis of some 3-(arylalkylthio)-4-alkyl/aryl-5-(4-aminophenyl)-4H-1,2,4-triazole derivatives and their anticonvulsant activity. Farmaco 2004;59:893–901.
  • Kehne JH, Kane JM, Chaney SF, et al. Preclinical characterization of MDL 27,192 as a potential broad spectrum anticonvulsant agent with neuroprotective properties. Epilepsy Res 1997;27:41–54.
  • Erdeniz H, Güniz KS, Rollas S, et al. Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines. Eur J Med Chem 2000;35:761–71.
  • Shalini M, Yogeeswari P, Sriram D, et al. Cyclization of the semicarbazone template of aryl semicarbazones: synthesis and anticonvulsant activity of 4,5-diphenyl-2H-1,2,4-triazol-3(4H)-one. Biomed Pharmacother 2009;63:187–93.
  • Yogeeswari P, Patel SK, Reddy IV, et al. GABA derivatives for the treatment of epilepsy and neuropathic pain: a synthetic integration of GABA in 1, 2, 4-Triazolo-2H-one nucleus. Biomed Aging Pathol 2012;2:31–40.
  • Shu B, Zheng Y, Wang SB, et al. Design, synthesis, and anticonvulsant activity evaluation of 4-(3-Alkoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-ones. Arch Pharm (Weinheim) 2013;346:127–33.
  • Cao X, Wang SB, Shu B, et al. Synthesis and anticonvulsant activity evaluation of 4-(2-alkoxy-phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-ones in various experimental seizure models in mice. Drug Res 2013;63:319.
  • Cui J, Yin XM, Yuan MH, et al. Synthesis and anticonvulsant activity evaluation of novel 4-(4-alkoxyphenyl)-3-ethyl-1H-1,2,4-triazol-5(4H)-ones. Chin J Med Chem 2014;24:188–95.
  • Zheng Y, Wang SB, Cao X, et al. Design, synthesis and anticonvulsant activity evaluation of novel 4-(4-substitutedphenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones. Drug Res 2014;64:40–6.
  • Zhu ZS, Wang SB, Deng XQ, et al. Synthesis and anticonvulsant activity evaluation of 4-butyl-5-(4-alkoxyphenyl)-2H-1,2,4-triazol-3(4H)-ones. Lett Drug Des. Discovery 2014;11:628–35.
  • Zhi H, Yuan YP, Quan ZS. Synthesis and anticonvulsant activity evaluation of novel 4-(4-methoxybenzyl/phenethyl)-2H-1,2,4-triazol-3(4H)-ones. Chin J Med Chem 2015;25:361–8.
  • Kahveci B, Menteşe E, Akkaya E, et al. Synthesis of some novel 1,2,4-triazol-3-one derivatives bearing the salicyl moiety and their anticonvulsant activities. Arch Pharm 2014;347:449–55.
  • Gülerman N, Rollas S, Kiraz M, et al. Evaluation of antimycobacterial and anticonvulsant activities of new 1-(4-fluorobenzoyl)-4-substituted-thiosemicarbazide and 5-(4-fluorophenyl)-4-substituted-2,4-dihydro-3H-1,2,4-triazole-3-thione derivatives. Farmaco 1997;52:691–5.
  • Khanum SA, Shashikanth S, Sudha BS. Synthesis and biological evaluation of 3-(2-aroylaryloxy)methyl-5-mercapto-4H-1,2,4-triazole analogues. Indian J Pharm Sci 2004;66:293–9.
  • Pandeya SN, Sriram D, Yogeeswari P, et al. Anticonvulsant and neurotoxicity evaluation of 5-(un)-substituted isatinimino derivatives. Pharmazie 2008;56:875–6.
  • Siddiqui N, Alam MS, Ahsan W. Synthesis, anticonvulsant and toxicity evaluation of 2-(1H-indol-3-yl)acetyl-N-(substituted phenyl)hydrazine carbothioamides and their related heterocyclic derivative. Acta Pharm 2008;58:445–54.
  • Siddiqui N, Ahsan W. Triazole incorporated thiazoles as a new class of anticonvulsants: Design, synthesis and in vivo screening. Eur J Med Chem 2010;45:1536–43.
  • Bhat MA, Al-Omar MA. Coumarin incorporated triazoles: a new class of anticonvulsants. Acta Pol Pharm 2011;68:889–95.
  • Kumudha D, Venkatanarayanan R, Kalavathi T, et al. Synthesis and pharmacological investigation of some Schiff’s bases, 4-thiazolidinones having 1, 2, 4-triazole moiety. World J Pharm 2015;4:1339–56.
  • Botros S, Khalil NA, Naguib BH, et al. Synthesis and anticonvulsant activity of new phenytoin derivatives. Eur J Med Chem 2013;60:57–63.
  • Kumudha D, Leonard JT, Muthumani M, et al. Synthesis and evaluation of 1,2,4-triazole derivatives as anticonvulsant, anti-inflammatory and antimocrobial agents. Asian J Pharm Clin Res 2013;6:5–8.
  • Plech T, Luszczki JJ, Wujec M, et al. Synthesis, characterization and preliminary anticonvulsant evaluation of some 4-alkyl-1,2,4-triazoles. Eur J Med Chem 2013;60:208–15.
  • Kumudha D, Kalavathi T, Venkatanarayanan R, et al. Synthesis and evaluation of pharmacological activities of some 1,3,4-oxadiazoles,1,2,4-triazoles possessing s-triazolemoiety. World J Pharm Res 2014;3:526–37.
  • Kumudha D, Reddy RR, Kalavathi T. Synthesis and evaluation of some 1,3,4-thiadiazoles having substituted 1, 2, 4-triazole moiety for anticonvulsant and CNS depressant activity. World J Pharm Pharm Sci 2014;3:728–40.
  • Plech T, Kaproń B, Luszczki JJ, et al. Studies on the anticonvulsant activity and influence on GABA-ergic neurotransmission of 1,2,4-triazole-3-thione-based compounds. Molecules 2014;19:11279–99.
  • Plech T, Kaproń B, Luszczki JJ, et al. Studies on the anticonvulsant activity of 4-alkyl-1,2,4-triazole-3-thiones and their effect on GABAergic system. Eur J Med Chem 2014;86:690–9.
  • Garg N, Chandra T, Lata S, et al. Synthesis and evaluation of some newer indole derivatives as anticonvulsant agents. Org Chem Indian J 2009;5:208–14.
  • Prakash CR, Raja S, Saravanan G. Synthesis and anti-epileptic activity of some novel 3-(4-(4-(substituted benzylideneamino)-5-mercapto-4-1,2,4-triazole-3-yl)phenylimino)-1-((dimethyl amino)methyl)-5-fluoroindolin-2-one derivatives. Int J Pharm Pharm Sci 2014;6:539–44.
  • Ulloora S, Shabaraya R, Adhikari AV. New 6-bromoimidazo[1,2-a]pyridine-2-carbohydrazide derivatives: synthesis and anticonvulsant studies. Med Chem Res 2013;23:3019–28.
  • Said SA, Said SA, Amr A-G, Sabry NM, et al. Analgesic, anticonvulsant and anti-inflammatory activities of some synthesized benzodiazipine, triazolopyrimidine and bis-imide derivatives. Eur J Med Chem 2009;44:4787–92.
  • Guan LP, Sui X, Chang Y, et al. Design, synthesis and anticonvulsant activity evaluation of 7-substituted-[1,2,4]-triazolo[4,3-f]pyrimidine derivatives. Med Chem 2012;8:1076–83.
  • Divate VA, Dhongade-Desai S. An efficient microwave assisted multicomponent synthesis of some 7-amino-3-(substituted phenyl)-5-(substituted phenyl)-[1,2,4]triazolo[4,3a] pyrimidine-6-carbonitrile derivatives. Int J Curr Pharm Res 2014;6:20–4.
  • Faizi M, Dabirian S, Tajali H, et al. Novel agonists of benzodiazepine receptors: design, synthesis, binding assay and pharmacological evaluation of 1,2,4-triazolo[1,5-a]pyrimidinone and 3-amino-1,2,4-triazole derivatives. Bioorg Med Chem 2015;23:480–7.
  • Jiang N, Deng XQ, Li FN, et al. Synthesis of novel 7-substituted-5-phenyl-[1,2,4]triazolo [1,5-a] pyrimidines with anticonvulsant activity. Iran J Pharm Res 2012;11:799–806.
  • Guan LP, Sui X, Deng XQ, et al. Synthesis and anticonvulsant activity of a new 6-alkoxy-[1,2,4]triazolo[4,3-b]pyridazine. Eur J Med Chem 2010;45:1746–52.
  • Guan LP, Zhang RP, Chang Y, et al. Synthesis and Studies on Anticonvulsant Activity of 8-Alkoxy-[1,2,4]triazolo[4,3-a]pyrazine. Asian J Chem 2013;25:3660–4.
  • Guan LP, Zhang RP, Sun Y, et al. Synthesis and studies on the anticonvulsant activity of 5-alkoxy-[1,2,4]triazolo[4,3-a]pyridine derivatives. Arzneimittelforschung 2012;62:372–7.
  • Vijaya Raj KK, Narayana B. The one step synthesis of 2-(2-Bromo-5-methoxyphenyl)-5-(3-arylidene)-1,3-thiazolo[3,2-b]-1,2,4-triazol-6-(5H)-ones and the evaluation of the anticonvulsant activity. Phosphorus Sulfur Silicon Relat Elem 2006;181:1971–81.
  • Song MX, Zhang CB, Deng XQ, et al. Synthesis and anticonvulsant activity evaluation of 6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines. Lett Drug Des Discov 2011;8:769–73.
  • Deng XQ, Song MX, Gong GH, et al. Synthesis and anticonvulsant evaluation of some new 6-(substituted-phenyl)thiazolo[3,2-b][1,2,4]triazole derivatives in mice[J]. Iran J Pharm Res 2014;13:459–69.
  • Husain A, Naseer MA, Sarafroz M. Synthesis and anticonvulsant activity of some novel fused heterocyclic 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives. Acta Pol Pharm 2009;66:135–40.
  • Deng XQ, Dong ZQ, Song MX, et al. Synthesis and anticonvulsant activities of some triazolothiadiazole derivatives. Arch Pharm Chem Life Sci 2012;345:565–73.
  • Kamble RR, Sudha BS, Ravindra RK, Belagur SS. An efficient synthesis of pharmacologically active derivatives of 1,3,4-oxadiazoles. J Heterocycl Chem 2006;43:345–51.
  • Cui LJ, Xie ZF, Piao HR, et al. Synthesis and anticonvulsant activity of 1-substituted-7-benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline. Biol Pharm Bull 2005;28:1216–20.
  • Xie ZF, Chai KY, Piao HR, et al. Synthesis and anticonvulsant activity of 7-alkoxyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolines. Bioorg Med Chem Lett 2005;15:4803–5.
  • Jin YZ, Guan LP, Zhao LM, et al. Synthesis and anticonvulsant activity study of 7-substituted phenoxyl-4,5-dihydro[1,2,4]triazolo[4,3-a]quinolines and quinoline-1(2H)-ones. Chin J Org Chem 2007;27:1567–72.
  • Cui XS, Guan LP, Li HL, et al. Synthesis and anticonvulsant activity of 7-benzylamino-4,5-dihydro-[1,2,4] triazolo[4,3-a] quinolines. Prog Nat Sci 2007;17:1104–8.
  • Wei CX, Deng XQ, Chai KY, et al. Synthesis and anticonvulsant activity of 1-formamide-triazolo[4,3-a]quinoline derivatives. Arch Pharm Res 2010;33:655–62.
  • Guan LP, Jin QH, Tian GR, et al. Synthesis of some quinoline-2(1H)-one and 1, 2, 4-triazolo [4,3 -a] quinoline derivatives as potent anticonvulsants. J Pharm Pharm Sci 2007;10:254–62.
  • Guan LP, Sun XY, Tian GR, et al. The synthesis and anticonvulsant activity of 1-substituted-7-methoxy-1,2,4-triazolo [4, 3-a]quinoline. Turk J Chem 2008;32:181–9.
  • Guan LP, Jin QH, Wang SF, et al. Synthesis and anticonvulsant activity of 5-phenyl-[1,2,4]-triazolo[4,3-a]quinolines. Arch Pharm (Weinheim) 2008;341:774–9.
  • Guan LP, Zhao DH, Jiang Z, et al. Evaluation of anticonvulsant activity of QUAN-0806 in various murine experimental seizure models. Pharmazie 2009;64:248–51.
  • Guo LJ, Wei CX, Jia JH, et al. Design and synthesis of 5-alkoxy-[1,2,4]triazolo[4,3-a] quinoline derivatives with anticonvulsant activity. Eur J Med Chem 2009;44:954–8.
  • Deng XQ, Quan ZS, Xiao CR, et al. Synthesis and anticonvulsant activity of substituted[1,2,4]triazolo[4,3-a]quinazolines. Chin J Org Chem 2011;31:2082–7.
  • Deng XQ, Quan LN, Song MX, et al. Synthesis and anticonvulsant activity of 7-phenyl-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones and their derivatives. Eur J Med Chem 2011;46:2955–63.
  • Kawade DP, Khedekar PB. Synthesis and anticonvulsant activity of some new 1,6-diphenyl-10,10a-dihydropyrido [2,3-d]-1,2,4- triazolo[4,3-a]pyrimidin-5(1H)-one derivatives. Int J Pharm Sci Res 2014;8:3409–17.
  • Zheng Y, Bian M, Deng XQ, et al. Synthesis and anticonvulsant activity evaluation of 5-phenyl-[1,2,4]triazolo[4,3-c]quinazolin-3-amines. Arch Pharm Chem Life Sci 2013;346:119–26.
  • Zhang CB, Yang CW, Deng XQ, et al. Design and synthesis of 6-alkyoxyl[1,2,4]triazolo [1,5-a]quinazoline derivatives with anticonvulsant activity. Med Chem Res 2012;21:3294–300.
  • Zhang HJ, Jin P, Wang SB, et al. Synthesis and anticonvulsant activity evaluation of 4-phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one and its derivatives. Arch Pharm (Weinheim) 2015;348:564–74.
  • Wang SB, Piao GC, Zhang HJ, et al. Synthesis of 5-alkoxythieno[2,3-e][1,2,4]triazolo [4,3-c]pyrimidine derivatives and evaluation of their anticonvulsant activities. Molecules 2015;20:6827–43.
  • Zhang L, Guan LP, Sun XY, et al. Synthesis and anticonvulsant activity of 6-alkoxy-[1,2,4]triazolo[3,4-a]phthalazines. Chem Biol Drug Des 2009;73:313–9.
  • Bian M, Deng XQ, Wei CX, et al. Synthesis and anticonvulsant activity evaluation of 6-substituted-[1,2,4]triazolo[3,4-a](tetrazolo[5,1-a])phthalazine derivatives. J Enzyme Inhib Med Chem 2013;28:792.
  • Dong ZQ, Liu XM, Wei CX, et al. Design, synthesis of 6-substituted-pyrido[3,2-d] pyridazine derivatives with anticonvulsant activity. Med Chem 2015;11:595–601.
  • Catarzi D, Lenzi O, Colotta V, et al. Pharmacological characterization of some selected 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates and 3-hydroxyquinazoline-2,4-diones as (S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)-propionic acid receptor antagonists. Chem Pharm Bull 2010;58:908–11.
  • Bayoumi A, Ghiaty A, El-Morsy A, et al. Synthesis and evaluation of some new (1,2,4) triazolo(4,3-a)quinoxalin-4(5H)-one derivatives as AMPA receptor antagonists. Bull Fac Pharm (Cairo Univ.) 2012;50:141–6.
  • Wagle S, Adhikari AV, Kumaris NS. Synthesis of some new 4-styryltetrazolo[1,5-a] quinoxaline and 1-substituted-4-styryl[1,2,4]triazolo[4,3-a]quinoxaline derivatives as potent anticonvulsants. Eur J Med Chem 2009;44:1135–43.
  • Alswah M, Ghiaty A, El-Morsy A, et al. Synthesis and biological evaluation of some [1,2,4]triazolo[4,3-a]quinoxaline derivatives as novel anticonvulsant agents. ISRN Org Chem 2013;article ID:587054.
  • Zhang LQ, Guan LP, Wei CX, et al. Synthesis and anticonvulsant activity of some 7-alkoxy-2H-1,4-benzothiazin-3(4H)-ones and 7-alkoxy-4H-[1,2,4]triazolo[4, 3-d]benzo[b][1,4]thiazines. Chem Pharm Bull 2010;58:326–31.
  • Deng XQ, Song MX, Wei CX, et al. Synthesis and anticonvulsant activity of 7-alkoxy-triazolo-[3, 4-b]benzo[d]thiazoles. Med Chem 2010;6:313–20.
  • Walser A, Benjamin LE, Flynn T, et al. Quinazolines and 1,4-benzodiazepines. 84. Synthesis and reactions of imidazo[1,5-a][1,4]benzodiazepines. J Org Chem 1978;43:936–44.
  • Phillips OA, Keshava Murthy KS, Fiakpui CY, et al. Synthesis of 6-phenyl-10-methyl-7H -pyrimido[4,5-f][1,2,4]triazolo[4,3-a][1,4]diazepine and its evaluation as an anticonvulsant agent. Can J Chem 1999;77:216–22.
  • Fiakpui CY, Phillips OA, Keshava Murthy KS, et al. Synthesis and anticonvulsant activities of 5-(2-chlorophenyl)-7H-pyrido[4,3-f][1,2,4]triazolo[4,3-a][1,4]diazepines. J Heterocycl Chem 1999;6:377–80.
  • Narayana B, Vijaya Raj KK, Ashalatha BV, et al. Synthesis of some new substituted triazolo[4,3-a][1,4]benzodiazepine derivatives as potent anticonvulsants. Eur J Med Chem 2006;41:417–22.
  • Caccia S, Grossi G, Fracasso C, et al. Acid-catalysed hydrolysis and benzodiazepine-like properties of 5-(dialkylamino)- and 5-(alkylthio)-substituted 8-chloro-6-phenyl-6H-[1,2,4]triazolol[4,3-a][1,5]benzodiazepines in mice. J Pharm Pharmacol 1998;50:723–8.
  • Shekarchi M, Marvasti MB, Sharifzadeh M, et al. Anticonvulsant activities of 7-phenyl-5H-thiazolo[5,4-e][1,2,3,4]tetrazolo[5,1-c]pyrrolo[1,2-a][1,4]diazepine and 7-phenyl-5H-thiazolo[5,4-e][1,3,4]triazolo[5,1-c] pyrrolo[1,2-a][1,4]diazepines. Iran J Pharm Res 2005;4:33–6.
  • Deng XQ, Wei CX, Li FN, et al. Design and synthesis of 10-alkoxy-5,6-dihydro-triazolo [4,3-d]benzo[f][1,4]oxazepine derivatives with anticonvulsant activity. Eur J Med Chem 2010;45:3080–6.
  • Deng XQ, Song MX, Wang SB, et al. Synthesis and evaluation of the anticonvulsant activity of 8-alkoxy-4,5-dihydrobenzo[b][1,2,4]triazolo[4,3-d][1,4]thiazepine derivatives. J Enzyme Inhib Med Chem 2014;29:272–80.
  • Zhang WB, Han RB, Zhang W, et al. Synthesis and anticonvulsant activity of 8-alkoxy-5,6-dihydro-4Hbenzo[f][1,2,4]triazolo[4,3-a]azepine derivatives. Med Chem Res 2012;21:2587–94.
  • Wu HF, Han RB, Jin CZ, et al. Synthesis of novel 8-alkylamino-5, 6-dihydro-4H-benzo[f][1,2,4]triazolo [4,3-a]azepines as anticonvulsant agents. CNS Neurol Disord Drug Targets 2016;15:1333–43.
  • Gill R, Lodge D. Pharmacology of AMPA antagonists and their role in neuroprotection. Int Rev Neurobiol. 1997;40:197–232.
  • Lees GJ. Therapeutic potential of AMPA/Kainate receptor ligands and their therapeutic potential in neurological disorders. Drugs 2000;59:33–78.
  • Lin Z, Kadaba PK. Molecular targets for the rational design of antiepileptic drugs and related neuroprotective agents. Med Res Rev 1997;17:537–72.
  • Rogawski MA, Donevan SD. AMPA receptors in epilepsy and as targets for antiepileptic drugs. Adv Neurol 1999;79:947–63.
  • De Sarro G, Chimirri A, De Sarro A, et al. GYKI 52466 and related 2,3-benzodiazepines as anticonvulsant agents in DBA/2 mice. Eur J Pharmacol 1995;294:411–22.
  • Chimirri A, De Sarro G, De Sarro A, et al. 1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists. J Med Chem 1997;40:1258–69.
  • Chimirri A, De Sarro G, De Sarro A, et al. 3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists. J Med Chem 1998;41:3409–16.
  • Chimirri A, Bevacqua F, Gitto R, et al. Synthesis and anticonvulsant activity of new 11H-triazolo[4,5-c][2,3]benzodiazepines. Med Chem Res 1999;9:203–12.
  • Zappalà M, Gitto R, Bevacqua F, et al. Synthesis and evaluation of pharmacological and pharmacokinetic properties of 11H-[1,2,4]Triazolo[4,5-c][2,3]benzodiazepin-3(2H)-ones. J Med Chem 2000;43:4834–9.
  • Gitto R, Orlando V, Quartarone S, et al. Synthesis and evaluation of pharmacological properties of novel annelated 2,3-benzodiazepine derivatives. J Med Chem 2003;46:3758–61.
  • Chimirri A, Gitto R, Quartarone S, et al. Synthesis and pharmacological properties of new 3-ethoxycarbonyl-11H-[1,2,4]triazolo[4,5-c][2,3]benzodiazepines. Farmaco 2002;57:759–63.
  • Nalbandyan GK, Mkrtchyan AP, Noravyan AS, et al. Condensed furopyrimidine derivatives. Part III. Synthesis and psychotropic activity of pyrano[4′,3′ : 4,5]furo[3,2-a]-1,2,4-triazolo-(tetrazolo)[4,3-a]pyrimidines. Pharm Chem J 1999;33:74–7.
  • Thore SN, Gupta SV, Baheti KG. Synthesis and pharmacological evaluation of novel triazolo [4, 3-a] tetrahydrobenzo (b) thieno [3, 2-e] pyrimidine-5(4 H)-ones. J Heterocycl Chem 2015;52:142–9.
  • Oganisyan AK, Noravyan AS, Dzhagatspanyan IA, et al. Derivatives of condensed thienopyrimidines: synthesis and neurotropic activity of new pyrano[4′,3′:4,5]thieno[3,2-e]triazolo[3,4-b]pyrimidine derivatives. Pharm Chem J 2003;37:13–4.
  • Jin HG, Sun XY, Chai KY, et al. Anticonvulsant and toxicity evaluation of some 7-alkoxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline-1(2H)-ones. Bioorg Med Chem 2006;14:6868–73.
  • Sun XY, Jin YZ, Li FN, et al. Synthesis of 8-alkoxy-4,5-dihydro-[1,2,4]triazole[4,3-a]quinoline-1-ones and evaluation of their anticonvulsant properties. Arch Pharm Sci Res 2006;29:1080–5.
  • Wei CX, Li FN, Zhao LX, et al. Synthesis of 2-substituted-7-heptyloxy-4,5-dihydro-[1,2,4]-triazolo[4,3-a]quinolin-1(2H)-ones with anticonvulsant activity. Arch Pharm (Weinheim) 2007;340:491–5.
  • Piao FY, Han RB, Zhang W, et al. Synthesis and anticonvulsant activity of 8-alkoxy-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1]benzazepin-1-one derivatives. Eur J Med Chem 2011;46:1050–5.
  • Piao FY, Han RB, Zhang W, et al. Synthesis and anticonvulsant activity of 9-alkoxy-6,7-dihydro-2H-benzo[c][1,2,4]triazolo[4,3-a]azepin-3[5H]-ones. Synth Commun 2012;43:2337–45.
  • Wei CX, Guo Z, Li FN, et al. Synthesis and anticonvulsant activity 6-alkoxy-[1,2,4]triazolo[3,4-a]phthalazin-3(2H)-ones. Asian J Chem 2011;23:127–31.
  • Cao X, Wang SB, Deng XQ, et al. Synthesis and anticonvulsant activity evaluation of 7-alkoxy-2, 4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-1-ones in various murine experimental seizure models. Med Chem Res 2014;23:1829–38.
  • Liu DC, Deng XQ, Wang SB, et al. Synthesis and anticonvulsant activity evaluation of 7-alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones. Arch Pharm (Weinheim) 2014;347:268–75.
  • Li H, Kang DZ, Wang SB, et al. Synthesis and evaluation of the anticonvulsant activity of 9-alkyl-2,9-dihydro-3H-1,2,4-triazolo[4,3-a]benzimidazole-3-one derivatives. Lat Am J Pharm 2015;34:5–12.
  • Zhang HJ, Shen QK, Jin CM, et al. Synthesis and pharmacological evaluation of new 3,4-dihydroisoquinolin derivatives containing heterocycle as potential anticonvulsant agents. Molecules 2016;21:e1635.
  • Brodie MJ, Rosenfeld WE, Vazquez B, et al. Rufinamide for the adjunctive treatment of partial seizures in adults and adolescents: a randomized placebo-controlled trial. Epilepsia 2009;50:1899–909.
  • Shukla JD, Arif Ali Khan PM, Deo K. Synthesis and pharmacological evaluation of novel 1-(2, 6-difluorobenzyl)-1H-1,2,3-triazole derivatives for CNS depressant and anticonvulsant profile. Am J PharmTech Res 2015;5:423–33.
  • Rivara M, Patel MK, Amori L, et al. Inhibition of NaV1.6 sodium channel currents by a novel series of 1,4-disubstituted-triazole derivatives obtained via copper-catalyzed click chemistry. Bioorg Med Chem Lett 2012;22:6401–4.
  • Ulloora S, Shabaraya R, Adhikari AV. Facile synthesis of new imidazo[1,2-a]pyridines carrying 1,2,3-triazoles via click chemistry and their antiepileptic studies. Bioorg Med Chem Lett 2013;23:3368–72.
  • Nassar EM, Abdelrazek FM, Ayyad RR, et al. Synthesis and some reactions of 1-aryl-4-acetyl-5-methyl-1,2,3-triazole derivatives with anticonvulsant activity. Mini-Rev Med Chem 2016;16:926–36.