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Synthesis and Evaluation of Anticonvulsant Activity of Some 5,5-Disubstituted-N3-[(2-aryl thiazolidine-4-one-3-yl)amino]hydantoins
Corresponding Author(s) : Dinesh Rishipathak
Asian Journal of Chemistry,
Vol. 35 No. 3 (2023): Vol 35 Issue 3, 2023
Abstract
According to the World Health Organization, the majority of people with epilepsy who live in developing countries do not have access to high-quality treatment. Modern anticonvulsants are in high demand since the unwanted effects of those compounds already in use make therapy difficult. The synthesis of derivatives of 5,5-disubstituted-N3-[(2-aryl thiazolidine-4-one-3-yl)amino]hydantoins has been reported. The position N3 of the hydantoin nucleus was substituted with 4-thiazolidinone moiety containing aryl substituent at 2nd position with the goal of achieving the enhanced anticonvulsant effect. Compounds 5c, 5d, 5l, 5r showed significant activity among the evaluated compounds compared to control at dose of 45 mg/kg. The analysis of structural features revealed that the substitution of p-hydroxy phenyl and cinnamyl substituted at 2nd position of thiazolidinone ring in 5,5-diphenyl-2,4-imidazolidinedione and p-chloro phenyl, p-methoxy phenyl substituted at 2nd position of thiazolidinone ring in (5,5-dialkyl)/(5-alkyl-5-substitutedphenyl)-2,4-imidazolidinedione skeleton enhanced the anticonvulsant potentiality of the synthesized compounds.
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- J.I. Sirven, Cold Spring Harb Perspect. Med., 5, a022848 (2015); https://doi.org/10.1101/cshperspect.a022848
- M. D’Antuono, R. Köhling, S. Ricalzone, J. Gotman, G. Biagini and M. Avoli, Epilepsia, 51, 423 (2010); https://doi.org/10.1111/j.1528-1167.2009.02273.x
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- P.N. Patsalos, D.J. Berry, B.F.D. Bourgeois, J.C. Cloyd, T.A. Glauser, S.I. Johannessen, I.E. Leppik, T. Tomson and E. Perucca, Epilepsa, 49, 1239 (2008); https://doi.org/10.1111/j.1528-1167.2008.01561.x
- S.H. Cho, S.-H. Kim and D. Shin, Eur. J. Med. Chem., 15, 517 (2019); https://doi.org/10.1016/j.ejmech.2018.12.066
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- W. Fischer, R. Bodewei and G. Satzinger, Naunyn Schmiedebergs Arch. Pharmacol., 346, 442 (1992); https://doi.org/10.1007/BF00171088
- V. Angelova, V. Karabeliov, P.A. AndreevaGateva and J. Tchekalarova, Drug Dev. Res., 77, 379 (2016); https://doi.org/10.1002/ddr.21329
- F.A. Neshan, M.S. Al-Rawi and J.H. Tomma, Int. J. Drug Deliv. Technol., 9, 587 (2019).
- D.D. Rishipathak, K.V. Patil, P.S. Wajpeyi and M.J. Daryani, Int. J. Pharm. Sci. Res., 7, 5044 (2016).
References
J.I. Sirven, Cold Spring Harb Perspect. Med., 5, a022848 (2015); https://doi.org/10.1101/cshperspect.a022848
M. D’Antuono, R. Köhling, S. Ricalzone, J. Gotman, G. Biagini and M. Avoli, Epilepsia, 51, 423 (2010); https://doi.org/10.1111/j.1528-1167.2009.02273.x
G.L. Birbeck, Epilepsy Curr., 10, 75 (2010); https://doi.org/10.1111/j.1535-7511.2010.01362.x
S. Cho, S.H. Kim and D. Shin, Eur. J. Med. Chem., 164, 517 (2019); https://doi.org/10.1016/j.ejmech.2018.12.066
P.N. Patsalos, D.J. Berry, B.F.D. Bourgeois, J.C. Cloyd, T.A. Glauser, S.I. Johannessen, I.E. Leppik, T. Tomson and E. Perucca, Epilepsa, 49, 1239 (2008); https://doi.org/10.1111/j.1528-1167.2008.01561.x
S.H. Cho, S.-H. Kim and D. Shin, Eur. J. Med. Chem., 15, 517 (2019); https://doi.org/10.1016/j.ejmech.2018.12.066
A.C. Tripathi, S.J. Gupta, G.N. Fatima, P.K. Sonar, A. Verma and S.K. Saraf, Eur. J. Med. Chem., 72, 52 (2014); https://doi.org/10.1016/j.ejmech.2013.11.017
A. Adhikari, B. Kalluraya, K.V. Sujith, K. Gouthamchandra and R. Mahmood, J. Adv. Res., 3, 325 (2012); https://doi.org/10.1016/j.jare.2011.10.003
H. Kaur, S. Kumar, P. Vishwakarma, M. Sharma, K.K. Saxena and A. Kumar, Eur. J. Med. Chem., 45, 2777 (2010); https://doi.org/10.1016/j.ejmech.2010.02.060
W. Fischer, R. Bodewei and G. Satzinger, Naunyn Schmiedebergs Arch. Pharmacol., 346, 442 (1992); https://doi.org/10.1007/BF00171088
V. Angelova, V. Karabeliov, P.A. AndreevaGateva and J. Tchekalarova, Drug Dev. Res., 77, 379 (2016); https://doi.org/10.1002/ddr.21329
F.A. Neshan, M.S. Al-Rawi and J.H. Tomma, Int. J. Drug Deliv. Technol., 9, 587 (2019).
D.D. Rishipathak, K.V. Patil, P.S. Wajpeyi and M.J. Daryani, Int. J. Pharm. Sci. Res., 7, 5044 (2016).