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Microwave Assisted Synthesis and Evaluation of Anticonvulsant Activity of Some 3-(3-(Substituted benzylidine)amino)phenyl-2-phenylquinazolin-4(3H)-ones
Corresponding Author(s) : Dinesh Rishipathak
Asian Journal of Chemistry,
Vol. 35 No. 1 (2023): Vol 35 Issue 1
Abstract
Herein, the synthesis of 3-(3-(substituted benzylidine)amino)phenyl-2-phenylquinazolin-4(3H)-ones from 3-aminophenyl-2-phenyl-quinazolin-4(3H)-ones is reported. The chemical structures of the synthesized compounds were confirmed by FT-IR, 1H NMR and 13C NMR studies. All compounds were evaluated for their anticonvulsant activity against maximal electroshock seizure method. The LD50 value was found to be 550 mg/Kg and the duration of tonic phase was reduced upto 1.1 s and that of stupor phase was reduced upto 70 s. The structure activity relationship of the compounds revealed that Schiff bases viz. 3-(3-benzylidineamino)phenyl-2-phenylquinazolin-4(3H)-one, 3-(3-(3-chlorobenzylidine)amino)phenyl-2-phenylquinazolin-4(3H)-one, 3-(3-(3-nitrobenzylidine)amino)phenyl-2-phenylquinazolin-4(3H)-one by significantly shorten the tonic and stupor phases of convulsions compared to controls, thus thereby these compounds demonstrated strong anticonvulsant potential.
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- A. Cano, E. Fonseca, M. Ettcheto, E. Sánchez-López, I. de Rojas, S. Alonso-Lana, X. Morató, E.B. Souto, M. Toledo, M. Boada, M. Marquié and A. Ruíz, Pharmaceuticals, 14, 1057 (2021); https://doi.org/10.3390/ph14101057
- S.J. Nevitt, A.G. Marson, J. Weston and C.T. Smith, Cochrane Database Syst. Rev., 2017, CD001911 (2017); https://doi.org/10.1002/14651858.CD001911.pub3
- P. Satishchandra, N.S. Santhosh and S. Sinha, Ann. Indian Acad. Neurol., 17(Suppl 1), S3 (2014); https://doi.org/10.4103/0972-2327.128643
- R.D. Amrutkar, S.V. Amrutkar and M.S. Ranawat, Curr. Bioact. Comp., 16, 370 (2020); https://doi.org/10.2174/1573407215666181120115313
- M. Faisal and A. Saeed, Front. Chem., 8, 594717 (2021); https://doi.org/10.3389/fchem.2020.594717
- M. Rudrapal and B. De, Int. Res. J. Pure Appl. Chem., 3, 232 (2014); https://doi.org/10.9734/IRJPAC/2014/3996
- N. Jain, J. Jaiswal, A. Pathak and P.K. Singour, Cent. Nerv. Syst. Agents Med. Chem., 18, 63 (2018); https://doi.org/10.2174/1871524917666170104142033
- V.G. Ugale and S.B. Bari, Arch. Pharm., 349, 864 (2016); https://doi.org/10.1002/ardp.201600218
- Z. Chen, M.J. Brodie, D. Liew and P. Kwan, JAMA Neurol., 75, 279 (2018); https://doi.org/10.1001/jamaneurol.2017.3949
- E. Perucca, Acta Epileptol., 3, 22 (2021); https://doi.org/10.1186/s42494-021-00055-z
- A. Fattorusso, S. Matricardi, E. Mencaroni, G.B. Dell'Isola, G. Di Cara, P. Striano and A. Verrotti, Front. Neurol., 12, 674483 (2021); https://doi.org/10.3389/fneur.2021.674483
References
A. Cano, E. Fonseca, M. Ettcheto, E. Sánchez-López, I. de Rojas, S. Alonso-Lana, X. Morató, E.B. Souto, M. Toledo, M. Boada, M. Marquié and A. Ruíz, Pharmaceuticals, 14, 1057 (2021); https://doi.org/10.3390/ph14101057
S.J. Nevitt, A.G. Marson, J. Weston and C.T. Smith, Cochrane Database Syst. Rev., 2017, CD001911 (2017); https://doi.org/10.1002/14651858.CD001911.pub3
P. Satishchandra, N.S. Santhosh and S. Sinha, Ann. Indian Acad. Neurol., 17(Suppl 1), S3 (2014); https://doi.org/10.4103/0972-2327.128643
R.D. Amrutkar, S.V. Amrutkar and M.S. Ranawat, Curr. Bioact. Comp., 16, 370 (2020); https://doi.org/10.2174/1573407215666181120115313
M. Faisal and A. Saeed, Front. Chem., 8, 594717 (2021); https://doi.org/10.3389/fchem.2020.594717
M. Rudrapal and B. De, Int. Res. J. Pure Appl. Chem., 3, 232 (2014); https://doi.org/10.9734/IRJPAC/2014/3996
N. Jain, J. Jaiswal, A. Pathak and P.K. Singour, Cent. Nerv. Syst. Agents Med. Chem., 18, 63 (2018); https://doi.org/10.2174/1871524917666170104142033
V.G. Ugale and S.B. Bari, Arch. Pharm., 349, 864 (2016); https://doi.org/10.1002/ardp.201600218
Z. Chen, M.J. Brodie, D. Liew and P. Kwan, JAMA Neurol., 75, 279 (2018); https://doi.org/10.1001/jamaneurol.2017.3949
E. Perucca, Acta Epileptol., 3, 22 (2021); https://doi.org/10.1186/s42494-021-00055-z
A. Fattorusso, S. Matricardi, E. Mencaroni, G.B. Dell'Isola, G. Di Cara, P. Striano and A. Verrotti, Front. Neurol., 12, 674483 (2021); https://doi.org/10.3389/fneur.2021.674483