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Letters in Drug Design & Discovery

Editor-in-Chief

ISSN (Print): 1570-1808
ISSN (Online): 1875-628X

Review Article

An Active Group with Potential Anti-seizure Activity: A Review on 1,2,4- Triazoles

Author(s): Ying Wang, Zheshan Quan and Dachuan Liu*

Volume 20, Issue 8, 2023

Published on: 26 September, 2022

Page: [1005 - 1019] Pages: 15

DOI: 10.2174/1570180819666220623142537

Price: $65

Abstract

Background: Epilepsy is one of the most common neurological disorders. Many individuals continue to have seizures despite medical and surgical treatments, suggesting that the discovery of novel anti-seizure drugs is vital. Triazole compounds are widely used as pharmaceuticals and have gained significant interest in medicinal chemistry. In this article, the development of triazoles, especially 1,2,4- triazole, in the field of anti-seizure therapeutics is reviewed.

Methods: The relevant literature was investigated, classified, and analysed. This article attempts to systematically review the research of triazole derivatives in the design and development of anti-seizure agents during the past two decades through extensive literature research, which was based on the information accessible in PubMed, Science Direct, Google Scholar and other databases.

Results: Research results demonstrate that triazoles occupy a distinct niche in heterocyclic chemistry and represent a key motif in medicinal chemistry because of their ability to exhibit an array of properties and bioactivities. Therefore, 1,2,4-triazole appears to be an important pharmacophore, especially in the field of anti-seizure therapeutics, where its promising potential value has been explored.

Conclusion: This review presents a summary of the research related to 1,2,4-triazole, which acts as a potential anti-seizure pharmacophore that could be further developed. Compounds with 1,2,4-triazole or related structures had previously shown reasonable anti-seizure activity and safety. After thorough research of this structure, it is believed that 1,2,4-triazole-containing compounds will be further developed as anti-seizure drugs for clinical use.

Keywords: Triazoles, anti-seizure, heterocycles, maximal electroshock test (MES), pentylenetetrazol (PTZ), protective index (PI).

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[1]
Beghi, E.; Giussani, G.; Nichols, E.; Abd-Allah, F.; Abdela, J.; Abdelalim, A.; Abraha, H.N.; Adib, M.G.; Agrawal, S.; Alahdab, F.; Awasthi, A.; Ayele, Y.; Barboza, M.A.; Belachew, A.B.; Biadgo, B.; Bijani, A.; Bitew, H.; Carvalho, F.; Chaiah, Y.; Daryani, A.; Do, H.P.; Dubey, M.; Endries, A.Y.Y.; Eskandarieh, S.; Faro, A.; Farzadfar, F.; Fereshtehnejad, S-M.; Fernandes, E.; Fijabi, D.O.; Filip, I.; Fischer, F.; Gebre, A.K.; Tsadik, A.G.; Gebremichael, T.G.; Gezae, K.E.; Ghasemi-Kasman, M.; Weldegwergs, K.G.; Degefa, M.G.; Gnedovskaya, E.V.; Hagos, T.B.; Haj-Mirzaian, A.; Haj-Mirzaian, A.; Hassen, H.Y.; Hay, S.I.; Jakovljevic, M.; Kasaeian, A.; Kassa, T.D.; Khader, Y.S.; Khalil, I.; Khan, E.A.; Khubchandani, J.; Kisa, A.; Krohn, K.J.; Kulkarni, C.; Nirayo, Y.L.; Mackay, M.T.; Majdan, M.; Majeed, A.; Manhertz, T.; Mehndiratta, M.M.; Mekonen, T.; Meles, H.G.; Mengistu, G.; Mohammed, S.; Naghavi, M.; Mokdad, A.H.; Mustafa, G.; Irvani, S.S.N.; Nguyen, L.H.; Nixon, M.R.; Ogbo, F.A.; Olagunju, A.T.; Olagunju, T.O.; Owolabi, M.O.; Phillips, M.R.; Pinilla-Monsalve, G.D.; Qorbani, M.; Radfar, A.; Rafay, A.; Rahimi-Movaghar, V.; Reinig, N.; Sachdev, P.S.; Safari, H.; Safari, S.; Safiri, S.; Sahraian, M.A.; Samy, A.M.; Sarvi, S.; Sawhney, M.; Shaikh, M.A.; Sharif, M.; Singh, G.; Smith, M.; Szoeke, C.E.I.; Tabarés-Seisdedos, R.; Temsah, M-H.; Temsah, O.; Tortajada-Girbés, M.; Tran, B.X.; Tsegay, A.A.T.; Ullah, I.; Venketasubramanian, N.; Westerman, R.; Winkler, A.S.; Yimer, E.M.; Yonemoto, N.; Feigin, V.L.; Vos, T.; Murray, C.J.L. Global, regional, and national burden of epilepsy, 1990-2016: A systematic analysis for the Global Burden of Disease Study 2016. Lancet Neurol., 2019, 18(4), 357-375.
[http://dx.doi.org/10.1016/S1474-4422(18)30454-X] [PMID: 30773428]
[2]
Fisher, R.S.; Acevedo, C.; Arzimanoglou, A.; Bogacz, A.; Cross, J.H.; Elger, C.E.; Engel, J., Jr; Forsgren, L.; French, J.A.; Glynn, M.; Hesdorffer, D.C.; Lee, B.I.; Mathern, G.W.; Moshé, S.L.; Perucca, E.; Scheffer, I.E.; Tomson, T.; Watanabe, M.; Wiebe, S. ILAE official report: A practical clinical definition of epilepsy. Epilepsia, 2014, 55(4), 475-482.
[http://dx.doi.org/10.1111/epi.12550] [PMID: 24730690]
[3]
Kalilani, L.; Sun, X.; Pelgrims, B.; Noack-Rink, M.; Villanueva, V. The epidemiology of drug-resistant epilepsy: A systematic review and meta-analysis. Epilepsia, 2018, 59(12), 2179-2193.
[http://dx.doi.org/10.1111/epi.14596] [PMID: 30426482]
[4]
Taylor, A.P.; Robinson, R.P.; Fobian, Y.M.; Blakemore, D.C.; Jones, L.H.; Fadeyi, O. Modern advances in heterocyclic chemistry in drug discovery. Org. Biomol. Chem., 2016, 14(28), 6611-6637.
[http://dx.doi.org/10.1039/C6OB00936K] [PMID: 27282396]
[5]
Grover, G.; Nath, R.; Bhatia, R.; Akhtar, M.J. Synthetic and therapeutic perspectives of nitrogen containing heterocycles as anti-convulsants. Bioorg. Med. Chem., 2020, 28(15), 115585.
[http://dx.doi.org/10.1016/j.bmc.2020.115585] [PMID: 32631563]
[6]
Aggarwal, R.; Sumran, G. An insight on medicinal attributes of 1,2,4-triazoles. Eur. J. Med. Chem., 2020, 205, 112652.
[http://dx.doi.org/10.1016/j.ejmech.2020.112652] [PMID: 32771798]
[7]
Kaproń, B.; Łuszczki, J.J.; Siwek, A.; Karcz, T.; Nowak, G.; Zagaja, M.; Andres-Mach, M.; Stasiłowicz, A.; Cielecka-Piontek, J.; Kocki, J.; Plech, T. Preclinical evaluation of 1,2,4-triazole-based compounds targeting voltage-gated sodium channels (VGSCs) as promising anticonvulsant drug candidates. Bioorg. Chem., 2020, 94, 103355.
[http://dx.doi.org/10.1016/j.bioorg.2019.103355] [PMID: 31662213]
[8]
Shahzad, S.A.; Yar, M.; Khan, Z.A.; Shahzadi, L.; Naqvi, S.A.R.; Mahmood, A.; Ullah, S.; Shaikh, A.J.; Sherazi, T.A.; Bale, A.T.; Kukułowicz, J.; Bajda, M. Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs. Bioorg. Chem., 2019, 85, 209-220.
[http://dx.doi.org/10.1016/j.bioorg.2019.01.005] [PMID: 30634096]
[9]
El-Sherief, H.A.M.; Youssif, B.G.M.; Abbas Bukhari, S.N.; Abdelazeem, A.H.; Abdel-Aziz, M.; Abdel-Rahman, H.M. Synthesis, anticancer activity and molecular modeling studies of 1,2,4-triazole derivatives as EGFR inhibitors. Eur. J. Med. Chem., 2018, 156, 774-789.
[http://dx.doi.org/10.1016/j.ejmech.2018.07.024] [PMID: 30055463]
[10]
Wittine, K.; Stipković Babić, M.; Makuc, D.; Plavec, J.; Kraljević Pavelić, S.; Sedić, M.; Pavelić, K.; Leyssen, P.; Neyts, J.; Balzarini, J.; Mintas, M. Novel 1,2,4-triazole and imidazole derivatives of L-ascorbic and imino-ascorbic acid: Synthesis, anti-HCV and antitumor activity evaluations. Bioorg. Med. Chem., 2012, 20(11), 3675-3685.
[http://dx.doi.org/10.1016/j.bmc.2012.01.054] [PMID: 22555152]
[11]
Küçükgüzel, I.; Tatar, E.; Küçükgüzel, S.G.; Rollas, S.; De Clercq, E. Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur. J. Med. Chem., 2008, 43(2), 381-392.
[http://dx.doi.org/10.1016/j.ejmech.2007.04.010] [PMID: 17583388]
[12]
Zhang, S.; Xu, Z.; Gao, C.; Ren, Q.C.; Chang, L.; Lv, Z.S.; Feng, L.S. Triazole derivatives and their anti-tubercular activity. Eur. J. Med. Chem., 2017, 138, 501-513.
[http://dx.doi.org/10.1016/j.ejmech.2017.06.051] [PMID: 28692915]
[13]
Barbieri, K.P.; Ercolin, L.D.R.; Louat, T.; Polesi, M.C.; Chin, C.M.; Zeppone, I.C.; Santos, J.L.D. Synthesis and immunosuppressive activity of new mycophenolic acid derivatives. Med. Chem., 2017, 13(2), 159-167.
[http://dx.doi.org/10.2174/1573406412666161207121226] [PMID: 27924728]
[14]
Jin, R.Y.; Zeng, C.Y.; Liang, X.H.; Sun, X.H.; Liu, Y.F.; Wang, Y.Y.; Zhou, S. Design, synthesis, biological activities and DFT calculation of novel 1,2,4-triazole Schiff base derivatives. Bioorg. Chem., 2018, 80, 253-260.
[http://dx.doi.org/10.1016/j.bioorg.2018.06.030] [PMID: 29966871]
[15]
Xu, J.; Cao, Y.; Zhang, J.; Yu, S.; Zou, Y.; Chai, X.; Wu, Q.; Zhang, D.; Jiang, Y.; Sun, Q. Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives. Eur. J. Med. Chem., 2011, 46(7), 3142-3148.
[http://dx.doi.org/10.1016/j.ejmech.2011.02.042] [PMID: 21420761]
[16]
Eswaran, S.; Adhikari, A.V.; Shetty, N.S. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. Eur. J. Med. Chem., 2009, 44(11), 4637-4647.
[http://dx.doi.org/10.1016/j.ejmech.2009.06.031] [PMID: 19647905]
[17]
Kahveci, B.; Yılmaz, F.; Menteşe, E.; Ülker, S. Design, synthesis, and biological evaluation of coumarin-triazole hybrid molecules as potential antitumor and pancreatic lipase agents. Arch. Pharm. (Weinheim), 2017, 350(8), 10.
[http://dx.doi.org/10.1002/ardp.201600369] [PMID: 28543820]
[18]
Meunier, B. Hybrid molecules with a dual mode of action: Dream or reality? Acc. Chem. Res., 2008, 41(1), 69-77.
[http://dx.doi.org/10.1021/ar7000843] [PMID: 17665872]
[19]
Shaveta, M.; Mishra, S.; Singh, P. Hybrid molecules: The privileged scaffolds for various pharmaceuticals. Eur. J. Med. Chem., 2016, 124, 500-536.
[http://dx.doi.org/10.1016/j.ejmech.2016.08.039] [PMID: 27598238]
[20]
Walker, K.A.; Wallach, M.B.; Hirschfeld, D.R. 1-(Naphthylalkyl)-1H-imidazole derivatives, a new class of anticonvulsant agents. J. Med. Chem., 1981, 24(1), 67-74.
[http://dx.doi.org/10.1021/jm00133a015] [PMID: 7205879]
[21]
Wauquier, A.; Fransen, J.; Melis, W.; Ashton, D.; Janssen, P. Loreclezole (r 72 063): An anticonvulsant chemically unrelated to prototype antiepileptic drugs. Drug Dev. Res., 2010, 19(4), 375-392.
[http://dx.doi.org/10.1002/ddr.430190404]
[22]
Karakurt, A.; Aytemir, M.D.; Stables, J.P.; Ozalp, M.; Betül Kaynak, F.; Ozbey, S.; Dalkara, S. 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. (Weinheim), 2006, 339(9), 513-520.
[http://dx.doi.org/10.1002/ardp.200500248] [PMID: 16941729]
[23]
Lankau, H.J.; Unverferth, K.; Grunwald, C.; Hartenhauer, H.; Heinecke, K.; Bernöster, K.; Dost, R.; Egerland, U.; Rundfeldt, C. New GABA-modulating 1,2,4-oxadiazole derivatives and their anticonvulsant activity. Eur. J. Med. Chem., 2007, 42(6), 873-879.
[http://dx.doi.org/10.1016/j.ejmech.2006.12.022] [PMID: 17303289]
[24]
Wang, S.B.; Deng, X.Q.; Song, M.X.; Quan, Z.S. Synthesis and anticonvulsant activity evaluation of some 1-alkoxy-4-(1H-1,2,4-triazol-1-yl)phthalazines. Lett. Drug Des. Discov., 2012, 9(4), 409-414.
[http://dx.doi.org/10.2174/157018012799860024]
[25]
Wang, S.B.; Deng, X.Q.; Zheng, Y.; Zhang, H.J.; Quan, Z.S. Synthesis and anticonvulsant activity evaluation of 8-alkoxy-5-(4H-1,2,4-triazol-4-yl)quinoline derivatives. Arch. Pharm. Res., 2013, 36(1), 32-40.
[http://dx.doi.org/10.1007/s12272-013-0006-9] [PMID: 23328871]
[26]
Wang, S.B.; Jin, P.; Li, F.N.; Quan, Z.S. Synthesis and anticonvulsant activity of novel purine derivatives. Eur. J. Med. Chem., 2014, 84, 574-583.
[http://dx.doi.org/10.1016/j.ejmech.2014.07.074] [PMID: 25062008]
[27]
Wang, S.B.; Piao, G.C.; Zhang, H.J.; Quan, Z.S. 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(4), 6827-6843.
[http://dx.doi.org/10.3390/molecules20046827] [PMID: 25884556]
[28]
Yuan, Y.P.; Wang, S.B.; Gong, G.H.; Quan, Z.S. Synthesis and Studies on Anticonvulsant and Antibacterial Activities of 1-Alkyl-4-(4H-1,2,4-triazol-4-yl)piperidine Derivatives. Lett. Drug Des. Discov., 2014, 11(9), 1070-1078.
[http://dx.doi.org/10.2174/1570180811666140623204022]
[29]
Deng, X.Q.; Song, M.X.; Zheng, Y.; Quan, Z.S. Design, synthesis and evaluation of the antidepressant and anticonvulsant activities of triazole-containing quinolinones. Eur. J. Med. Chem., 2014, 73, 217-224.
[http://dx.doi.org/10.1016/j.ejmech.2013.12.014] [PMID: 24412497]
[30]
Fang, Y.Q.; Sun, C.L.; Liu, D.C.; Wang, S.B.; Quan, Z.S. Synthesis and Anticonvulsant Activity Evaluation of 3-alkoxy-4-(4-(hexyloxy/heptyloxy)phenyl)-4H-1,2,4 -triazole. Iran. J. Pharm. Res., 2015, 14(1), 77-87.
[PMID: 25561914]
[31]
Liu, C.F.; Zhang, H.J.; Quan, Z.S. 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(8), 833-839.
[http://dx.doi.org/10.2174/1570180813666160324173717]
[32]
Song, M.X.; Rao, B.Q.; Cheng, B.B.; Wu, Y.; Zeng, H.; Luo, Y.G.; Deng, X.Q. Design, Synthesis and Evaluation of the Antidepressant and Anticonvulsant Activities of Triazole-Containing Benzo[d]oxazoles. CNS Neurol. Disord. Drug Targets, 2017, 16(2), 187-198.
[http://dx.doi.org/10.2174/1871527315666160822112501] [PMID: 27549143]
[33]
Dehestani, L.; Ahangar, N.; Hashemi, S.M.; Irannejad, H.; Honarchian Masihi, P.; Shakiba, A.; Emami, S. Design, synthesis, in vivo and in silico evaluation of phenacyl triazole hydrazones as new anticonvulsant agents. Bioorg. Chem., 2018, 78, 119-129.
[http://dx.doi.org/10.1016/j.bioorg.2018.03.001] [PMID: 29550532]
[34]
Song, M.; Yan, R.; Zhang, Y.; Guo, D.; Zhou, N.; Deng, X. Design, synthesis, and anticonvulsant effects evaluation of nonimidazole histamine H3 receptor antagonists/inverse agonists containing triazole moiety. J. Enzyme Inhib. Med. Chem., 2020, 35(1), 1310-1321.
[http://dx.doi.org/10.1080/14756366.2020.1774573] [PMID: 32529860]
[35]
Cao, X.; Deng, X.Q.; Shu, B.; Wang, S.B.; Quan, Z.S. 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. (Stuttg.), 2013, 63(6), 319-325.
[http://dx.doi.org/10.1055/s-0033-1337978] [PMID: 23539424]
[36]
Song, M.X.; Huang, Y.S.; Zhou, Q.G.; Deng, X.Q.; Yao, X.D. Synthesis of ring-opened derivatives of triazole-containing quinolinones and their antidepressant and anticonvulsant activities. Bioorg. Chem., 2021, 106, 104505.
[http://dx.doi.org/10.1016/j.bioorg.2020.104505] [PMID: 33279249]
[37]
Shu, B.; Zheng, Y.; Wang, S.B.; Deng, X.Q.; Quan, Z.S. 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(2), 127-133.
[http://dx.doi.org/10.1002/ardp.201200201] [PMID: 23239508]
[38]
Zheng, Y.; Deng, X.Q.; Shu, B.; Wang, S.B.; Cao, X.; Quan, Z.S. Synthesis and Evaluation of the Anticonvulsant Activity of 5-alkylthio-4-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one Derivatives. Lett. Drug Des. Discov., 2013, 10(6), 543-549.
[http://dx.doi.org/10.2174/1570180811310060011]
[39]
Zheng, Y.; Wang, S.B.; Cao, X.; Liu, D.C.; Shu, B.; Quan, Z.S. Design, synthesis and anticonvulsant activity evaluation of novel 4-(4-substitutedphenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones. Drug Res. (Stuttg.), 2014, 64(1), 40-46.
[PMID: 23965799]
[40]
Shen, Q.K.; Wang, S.B.; Gong, G.H.; Yin, X.M.; Quan, Z.S. Synthesis and Analysis of Anticonvulsant Activities of New 4-[2-(4-alkoxybenzylamino)ethyl]- 2H-1,2,4-triazol-3(4H)-one Derivatives. Lett. Drug Des. Discov., 2015, 12(5), 430-438.
[http://dx.doi.org/10.2174/1570180812666141111235746]
[41]
Kahveci, B.; Menteşe, E.; Akkaya, E.; Yılmaz, F.; Doğan, I.S.; Ozel, A. Synthesis of some novel 1,2,4-triazol-3-one derivatives bearing the salicyl moiety and their anticonvulsant activities. Arch. Pharm. (Weinheim), 2014, 347(6), 449-455.
[http://dx.doi.org/10.1002/ardp.201300427] [PMID: 24623369]
[42]
Cui, J.; Yin, X.M.; Yuan, M.H.; Cao, X.; Quan, Z.S. Synthesis and anticonvulsant activity evaluation of novel 4-(4-alkoxyphenyl)-3-ethyl-1H-1,2,4-triazol-5(4H)-ones. Zhongguo Yaowu Huaxue Zazhi, 2014, 3(24), 188-195.
[43]
Zhi, H.; Yuan, Y.P.; Quan, Z.S. Synthesis and anticonvulsant activity of 4-(4-alkoxy-benzyl/phenylethyl)-2H-1,2,4-triazole-3(4H)-ones. Zhongguo Yaowu Huaxue Zazhi, 2015, 5(25), 361-368.
[44]
Song, M.X.; Wang, Z.Y.; He, S.H.; Yu, S.W.; Chen, S.L.; Guo, D.F.; Zhao, W.H.; Deng, X.Q. Synthesis and Evaluation of the Anticonvulsant Activities of 4-(2-(Alkylthio)benzo[d]oxazol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ones. Molecules, 2018, 23(4), 756.
[http://dx.doi.org/10.3390/molecules23040756] [PMID: 29587394]
[45]
Song, M.X.; Huang, Y.; Wang, S.; Wang, Z.T.; Deng, X.Q. Design, synthesis, and evaluation of anticonvulsant activities of benzoxazole derivatives containing the 1,2,4-triazolone moiety. Arch. Pharm. (Weinheim), 2019, 352(8), e1800313.
[http://dx.doi.org/10.1002/ardp.201800313] [PMID: 31330092]
[46]
Siddiqui, N.; Alam, M.S.; Ahsan, W. Synthesis, anticonvulsant and toxicity evaluation of 2-(1H-indol-3-yl)acetyl-N-(substituted phenyl)hydrazine carbothioamides and their related heterocyclic derivatives. Acta Pharm., 2008, 58(4), 445-454.
[http://dx.doi.org/10.2478/v10007-008-0025-0] [PMID: 19103578]
[47]
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(4), 1536-1543.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.062] [PMID: 20116140]
[48]
Bhat, M.A.; Al-Omar, M.A. Coumarin incorporated triazoles: A new class of anticonvulsants. Acta Pol. Pharm., 2011, 68(6), 889-895.
[PMID: 22125954]
[49]
Plech, T.; Luszczki, J.J.; Wujec, M.; Flieger, J.; Pizoń, M. Synthesis, characterization and preliminary anticonvulsant evaluation of some 4-alkyl-1,2,4-triazoles. Eur. J. Med. Chem., 2013, 60, 208-215.
[http://dx.doi.org/10.1016/j.ejmech.2012.11.026] [PMID: 23291122]
[50]
Plech, T.; Kaproń, B.; Luszczki, J.J.; Wujec, M.; Paneth, A.; Siwek, A.; Kołaczkowski, M.; Zołnierek, M.; Nowak, G. Studies on the anticonvulsant activity and influence on GABA-ergic neurotransmission of 1,2,4-triazole-3-thione- based compounds. Molecules, 2014, 19(8), 11279-11299.
[http://dx.doi.org/10.3390/molecules190811279] [PMID: 25090118]
[51]
Plech, T.; Kaproń, B.; Luszczki, J.J.; Paneth, A.; Siwek, A.; Kołaczkowski, M.; Żołnierek, M.; Nowak, G. 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, 690-699.
[http://dx.doi.org/10.1016/j.ejmech.2014.09.034] [PMID: 25226229]
[52]
Kaproń, B.; Łuszczki, J.J.; Płazińska, A.; Siwek, A.; Karcz, T.; Gryboś, A.; Nowak, G.; Makuch-Kocka, A.; Walczak, K.; Langner, E.; Szalast, K.; Marciniak, S.; Paczkowska, M.; Cielecka-Piontek, J.; Ciesla, L.M.; Plech, T. Development of the 1,2,4-triazole-based anticonvulsant drug candidates acting on the voltage-gated sodium channels. Insights from in-vivo, in-vitro, and in-silico studies. European journal of pharmaceutical sciences, 2019, 129, 42-57.
[53]
Kaproń, B.; Czarnomysy, R.; Wysokiń,ski, M.; Andrys, R.; Musilek, K.; Angeli, A.; Supuran, C.T.; Plech, T. 1,2,4-Triazole-based anticonvulsant agents with additional ROS scavenging activity are effective in a model of pharmacoresistant epilepsy. J. Enzyme Inhib. Med. Chem., 2020, 35(1), 993-1002.
[http://dx.doi.org/10.1080/14756366.2020.1748026] [PMID: 32253957]
[54]
Makuch-Kocka, A.; Andres-Mach, M.; Zagaja, M.; Śmiech, A.; Pizoń, M.; Flieger, J.; Cielecka-Piontek, J.; Plech, T. Effect of Chronic Administration of 5-(3-chlorophenyl)-4-Hexyl-2,4 -Dihydro-3H-1,2,4-Triazole-3-Thione (TP-315)-A New Anticonvulsant Drug Candidate-On Living Organisms. Int. J. Mol. Sci., 2021, 22(7), 3358.
[http://dx.doi.org/10.3390/ijms22073358] [PMID: 33805962]
[55]
Drabik, M.; Głuszak, M.; Wróblewska-Łuczka, P.; Plewa, Z.; Jankiewicz, M.; Kozińska, J.; Florek-Łuszczki, M.; Plech, T.; Łuszczki, J.J. Anticonvulsant Effectiveness and Neurotoxicity Profile of 4-butyl-5-[(4-chloro-2-methylphenoxy)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione (TPL-16) in Mice. Neurochem. Res., 2021, 46(2), 396-410.
[http://dx.doi.org/10.1007/s11064-020-03175-z] [PMID: 33206316]
[56]
Husain, A.; Naseer, M.A.; 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(2), 135-140.
[PMID: 19719046]
[57]
Guan, L.P.; Sui, X.; Deng, X.Q.; Quan, Y.C.; Quan, Z.S. Synthesis and anticonvulsant activity of a new 6-alkoxy-[1,2,4]triazolo[4,3-b]pyridazine. Eur. J. Med. Chem., 2010, 45(5), 1746-1752.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.077] [PMID: 20116141]
[58]
Deng, X.Q.; Quan, L.N.; Song, M.X.; Wei, C.X.; Quan, Z.S. 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(7), 2955-2963.
[http://dx.doi.org/10.1016/j.ejmech.2011.04.020] [PMID: 21536355]
[59]
Song, M.X.; Zhang, C.B.; Deng, X.Q.; Sun, Z.G.; Quan, Z.S. 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(8), 769-773.
[http://dx.doi.org/10.2174/157018011796575962]
[60]
Deng, X.Q.; Dong, Z.Q.; Song, M.X.; Shu, B.; Wang, S.B.; Quan, Z.S. Synthesis and anticonvulsant activities of some triazolothiadiazole derivatives. Arch. Pharm. (Weinheim), 2012, 345(7), 565-573.
[http://dx.doi.org/10.1002/ardp.201100326] [PMID: 22532235]
[61]
Deng, X.Q.; Song, M.X.; Gong, G.H.; Wang, S.B.; Quan, Z.S. Synthesis and Anticonvulsant Evaluation of some New 6-(Substituted-phenyl)thiazolo[3,2-b][1,2,4]triazole Derivatives in Mice. Iran. J. Pharm. Res., 2014, 13(2), 459-469.
[PMID: 25237341]
[62]
Jiang, N.; Deng, X.Q.; Li, F.N.; Quan, Z.S. Synthesis of Novel 7-Substituted-5-phenyl-[1,2,4]triazolo[1,5-a] Pyrimidines with Anticonvulsant Activity. Iran. J. Pharm. Res., 2012, 11(3), 799-806.
[PMID: 24250507]
[63]
Guan, L.P.; Sui, X.; Chang, Y.; Yan, Z.S.; Tong, G.Z.; Qu, Y.L. Design, synthesis and anticonvulsant activity evaluation of 7-substituted-[1,2,4]-triazolo[4,3-f]pyrimidine derivatives. Med. Chem., 2012, 8(6), 1076-1083.
[PMID: 22779795]
[64]
Guan, L.P.; Zhang, R.P.; Sun, Y.; Chang, Y.; Sui, X. Synthesis and studies on the anticonvulsant activity of 5-alkoxy-[1,2,4]triazolo[4,3-a]pyridine derivatives. Arzneimittelforschung, 2012, 62(8), 372-377.
[http://dx.doi.org/10.1055/s-0032-1314821] [PMID: 22782505]
[65]
Huang, L.J.; Tian, Y.; Teng, D.W.; Li, X.F. A class of [1,2,4]- triazole[1,5-a]pyrimidone hetero cyclic compounds, their preparation methods and uses. China Patent CN106749271B 2019.
[66]
Ding, J.; Cao, F.D.; Geng, Y.R.; Tian, Y.; Li, P.; Li, X.F.; Huang, L.J. Synthesis and in vitro anti-epileptic activities of novel [1,2,4]-triazolo[1,5-a]pyrimidin-7(4H)-one derivatives. J. Asian Nat. Prod. Res., 2019, 21(12), 1190-1204.
[http://dx.doi.org/10.1080/10286020.2018.1529030] [PMID: 30593254]
[67]
Huang, L.; Ding, J.; Li, M.; Hou, Z.; Geng, Y.; Li, X.; Yu, H. Discovery of [1,2,4]-triazolo [1,5-a]pyrimidine-7(4H)-one derivatives as positive modulators of GABAA1 receptor with potent anticonvulsant activity and low toxicity. Eur. J. Med. Chem., 2020, 185, 111824.
[http://dx.doi.org/10.1016/j.ejmech.2019.111824] [PMID: 31708184]
[68]
Wagle, S.; Adhikari, A.V.; Kumari, N.S. 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(3), 1135-1143.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.006] [PMID: 18672315]
[69]
Havyarimana, L.; Ndendoung, S.T.; Tamokou, J.D.; Atchadé, A.T.; Tanyi, J.M. Chemical constituents of Millettia barteri and their antimicrobial and antioxidant activities. Pharm. Biol., 2012, 50(2), 141-146.
[http://dx.doi.org/10.3109/13880209.2011.579618] [PMID: 22338120]
[70]
Deng, X.Q.; Xiao, C.R.; Wei, X.C.; Quan, Z.S. Synthesis and anticonvulsant activity of substituted[1,2,4]triazolo[4,3-a]quinazolines. Youji Huaxue, 2011, 31(12), 2082-2087.
[71]
Zhang, H.J.; Jin, P.; Wang, S.B.; Li, F.N.; Guan, L.P.; Quan, Z.S. 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(8), 564-574.
[http://dx.doi.org/10.1002/ardp.201500115] [PMID: 26053879]
[72]
Dong, Z.Q.; Liu, X.M.; Wei, C.X.; Quan, Z.S. Design, synthesis of 6-substituted-pyrido[3,2-d]pyridazine derivatives with anticonvulsant activity. Med. Chem., 2015, 11(6), 595-601.
[http://dx.doi.org/10.2174/1573406411666150313152925] [PMID: 25770755]
[73]
Deng, X.Q.; Wei, C.X.; Li, F.N.; Sun, Z.G.; Quan, Z.S. 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(7), 3080-3086.
[http://dx.doi.org/10.1016/j.ejmech.2010.03.041] [PMID: 20416982]
[74]
Liu, X.J.; Zhang, H.J.; Quan, Z.S. Synthesis and evaluation of the anticonvulsant activities of 2,3-dihydrophthalazine-1,4-dione derivatives. Med. Chem. Res., 2017, 26(9), 1935-1946.
[http://dx.doi.org/10.1007/s00044-017-1896-8]
[75]
Zhang, G.R.; Ren, Y.; Yin, X.M.; Quan, Z.S. Synthesis and Evaluation of the Anticonvulsant Activities of New 5-substitued-[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one Derivatives. Lett. Drug Des. Discov., 2018, 15(4), 406-413.
[http://dx.doi.org/10.2174/1570180814666170619094408]
[76]
Deng, X.Q.; Song, M.X.; Wang, S.B.; Quan, Z.S. 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(2), 272-280.
[http://dx.doi.org/10.3109/14756366.2013.776555] [PMID: 23477412]
[77]
Wu, H.F.; Han, R.B.; Jin, C.Z.; Piao, F.Y. 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(10), 1333-1343.
[http://dx.doi.org/10.2174/1871527315666160321111211] [PMID: 26996166]
[78]
Jin, H.G.; Sun, X.Y.; Chai, K.Y.; Piao, H.R.; Quan, Z.S. 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(20), 6868-6873.
[http://dx.doi.org/10.1016/j.bmc.2006.06.044] [PMID: 16843667]
[79]
Sun, X.Y.; Jin, Y.Z.; Li, F.N.; Li, G.; Chai, K.Y.; Quan, Z.S. 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. Res., 2006, 29(12), 1080-1085.
[http://dx.doi.org/10.1007/BF02969295] [PMID: 17225454]
[80]
Piao, F.Y.; Han, R.B.; Zhang, W.; Zhang, W.B.; Jiang, R.S. 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(4), 1050-1055.
[http://dx.doi.org/10.1016/j.ejmech.2011.01.017] [PMID: 21303724]
[81]
Zhang, H.J.; Shen, Q.K.; Jin, C.M.; Quan, Z.S. Synthesis and Pharmacological Evaluation of New 3,4-Dihydroisoquinolin Derivatives Containing Heterocycle as Potential Anticonvulsant Agents. Molecules, 2016, 21(12), 1635.
[http://dx.doi.org/10.3390/molecules21121635] [PMID: 27916842]
[82]
Cao, X.; Wang, S.B.; Deng, X.Q.; Liu, D.C.; Quan, Z.S. 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(4), 1829-1838.
[http://dx.doi.org/10.1007/s00044-013-0778-y]
[83]
Liu, D.C.; Deng, X.Q.; Wang, S.B.; Quan, Z.S. Synthesis and anticonvulsant activity evaluation of 7-alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones. Arch. Pharm. (Weinheim), 2014, 347(4), 268-275.
[http://dx.doi.org/10.1002/ardp.201300277] [PMID: 24448887]
[84]
Mahdavi, M.; Akbarzadeh, T.; Sheibani, V.; Abbasi, M.; Firoozpour, L.; Tabatabai, S.A.; Shafiee, A.; Foroumadi, A. 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(3), 265-269.
[PMID: 24363736]
[85]
Zheng, Y.; Bian, M.; Deng, X.Q.; Wang, S.B.; Quan, Z.S. Synthesis and anticonvulsant activity evaluation of 5-phenyl-[1,2,4]triazolo[4,3-c]quinazolin-3-amines. Arch. Pharm. (Weinheim), 2013, 346(2), 119-126.
[http://dx.doi.org/10.1002/ardp.201200376] [PMID: 23255333]
[86]
Li, Y.C.; Deng, X.Q.; Quan, Z.S. Synthesis and anticonvulsant activity of 1,2,4-triazolo- 4-triazo[4,3-a]quinazolines. Zhongguo Yaowu Huaxue Zazhi, 2011, 21(1), 12-18.
[87]
Wang, S.; Liu, H.; Wang, X.; Lei, K.; Li, G.; Li, X.; Wei, L.; Quan, Z. Synthesis and evaluation of anticonvulsant activities of 7-phenyl-4,5,6,7-tetrahydrothieno[3,2-b]pyridine derivatives. Arch. Pharm. (Weinheim), 2019, 352(10), e1900106.
[http://dx.doi.org/10.1002/ardp.201900106] [PMID: 31364202]

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