Design, Synthesis and Anticonvulsant Evaluation of N-[(Substituted 1H-pyrazol-3-yl)amino]-2-(4-methylphenyl)quinazolin-4(3H)-one Derivatives

Sachin Kumar; K.K. Jha; Rati K.P. Tripathi; M. Shahar Yar

doi:10.14233/ajchem.2017.20523

Issue

Vol. 29 No. 6 (2017): Vol 29 Issue 6

Issue Published : April 10, 2017

This work is licensed under a Creative Commons Attribution 4.0 International License.

Design, Synthesis and Anticonvulsant Evaluation of N-[(Substituted 1H-pyrazol-3-yl)amino]-2-(4-methylphenyl)quinazolin-4(3H)-one Derivatives

https://doi.org/10.14233/ajchem.2017.20523

Sachin Kumar

Department of Pharmaceutical Chemistry, Teerthanker Mahaveer College of Pharmacy, Teerthanker Mahaveer University, Moradabad-244 001, India

K.K. Jha

Department of Pharmaceutical Chemistry, Teerthanker Mahaveer College of Pharmacy, Teerthanker Mahaveer University, Moradabad-244 001, India

Rati K.P. Tripathi

Department of Pharmaceutical Chemistry, Teerthanker Mahaveer College of Pharmacy, Teerthanker Mahaveer University, Moradabad-244 001, India

M. Shahar Yar

Department of Pharmaceutical Chemistry, Jamia Hamdard, New Delhi-110 062, India

Corresponding Author(s) : Sachin Kumar

sachin.pharmacy@tmu.ac.in

Asian Journal of Chemistry, Vol. 29 No. 6 (2017): Vol 29 Issue 6
Article Published : April 9, 2017

Abstract

A series of quinazolinone derivatives (7a-7e) have been designed, synthesized and evaluated for the anticonvulsant activity using maximal electroshock seizure (MES) model. The compound 3-[(5-(4-chloro)phenyl-4,5-dihydro-1H-pyrazol-3-yl)amino]-2-(4-methylphenyl)quinazolin-4(3H)-one (7c) was found to be most active compound showing 85.23 % protection and was found to be non-neurotoxic up to 4 h. This study indicates that the quinazolinone based derivatives could be further exploited for the discovery of newer and more effective anticonvulsant agents.

Keywords

Anticonvulsants Quinazolinone Maximal electroshock seizure (MES) model Neurotoxicity

Kumar, S., Jha, K., Tripathi, R. K., & Yar, M. S. (2017). Design, Synthesis and Anticonvulsant Evaluation of N-[(Substituted 1H-pyrazol-3-yl)amino]-2-(4-methylphenyl)quinazolin-4(3H)-one Derivatives. Asian Journal of Chemistry, 29(6), 1375–1379. https://doi.org/10.14233/ajchem.2017.20523

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References

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References

C.E. Stafstrom, J. Cereb. Blood Flow Metab., 26, 983 (2006); https://doi.org/10.1038/sj.jcbfm.9600265.

R. Hess, in eds. H.H. Frey and D. Janz, Electroencephalography, In: Antiepileptic Drugs, Series Handbook of Experimental Pharmacology, Springer-Verlag, Berlin, vol. 74, pp. 35-54 (1985).

M. Namara, G.J. Hardman, L.E. Limbird and A.G. Gilman, Drugs Effective in the Therapy of Epilepsies, McGraw-Hill, New York, pp. 521–548 (2001).

Z.P. Lin and K. Kadaba, Med. Res. Rev., 17, 537 (1997); https://doi.org/10.1002/(SICI)1098-1128(199711)17:6<537::AIDMED3>3.0.CO;2-2.

E. Vitaku, D.T. Smith and J.T. Njardarson, J. Med. Chem., 57, 10257 (2014); https://doi.org/10.1021/jm501100b.

M. Zappalã, S. Grasso, N. Micale, G. Zuccalã, F.S. Menniti, G. Ferreri, G. De Sarro and C. De Micheli, Bioorg. Med. Chem. Lett., 13, 4427 (2003); https://doi.org/10.1016/j.bmcl.2003.09.032.

J.K. Padia, M. Field, J. Hinton, K. Meecham, J. Pablo, R. Pinnock, B.D. Roth, L. Singh, N. Suman-Chauhan, B.K. Trivedi and L. Webdale, J. Med. Chem., 41, 1042 (1998); https://doi.org/10.1021/jm970373j.

A.R. El-Naser Ossman and S. El-Sayed Barakat, Arzneimittelforsch., 44, 915 (1994).

G. Grover and S.G. Kini, Eur. J. Med. Chem., 41, 256 (2006); https://doi.org/10.1016/j.ejmech.2005.09.002.

A.K. Tiwari, V.K. Singh, A. Bajpai, G. Shukla, S. Singh and A.K. Mishra, Eur. J. Med. Chem., 42, 1234 (2007); https://doi.org/10.1016/j.ejmech.2007.01.002.

N.M. Raghavendra, P. Thampi, P.M. Gurubasavarajaswamy and D. Sriram, Chem. Pharm. Bull. (Tokyo), 55, 1615 (2007); https://doi.org/10.1248/cpb.55.1615.

S.E.S. Abbas and A.E.M. Saafan, Bull. Pharm. Sci. Assuit Univ., 30, 51 (2007).

V. Alagarsamy, K. Dhanabal, P. Parthiban, G. Anjana, G. Deepa, B. Murugesan, S. Rajkumar and A.J. Beevi, J. Pharm. Pharmacol., 59, 669 (2007); https://doi.org/10.1211/jpp.59.5.0007.

V. Alagarsamy, V. Raja Solomon and K. Dhanabal, Bioorg. Med. Chem., 15, 235 (2007); https://doi.org/10.1016/j.bmc.2006.09.065.

V. Alagarsamy, V.R. Solomon and S. Murugesan, Arzneimittelforsch., 58, 174 (2008); https://doi.org/10.1055/s-0031-1296489.

E.B. Skibo, X. Huang, R. Martinez, R.H. Lemus, W.A. Craigo and R.T. Dorr, J. Med. Chem., 45, 5543 (2002); https://doi.org/10.1021/jm020285l.

S.N. Pandeya, Acta Pharm., 62, 263 (2012); https://doi.org/10.2478/v10007-012-0030-1.

M.F. Zayed, E.A. Ahmed, A.M. Omar, A.S. Abdelrahim and K. El-Adl, Med. Chem. Res., 22, 5823 (2013); https://doi.org/10.1007/s00044-013-0569-5.

N.W. Dunham and T.S. Miya, J. Am. Pharm. Assoc., 46, 208 (1957); https://doi.org/10.1002/jps.3030460322.

Issue

Vol. 29 No. 6 (2017): Vol 29 Issue 6

Design, Synthesis and Anticonvulsant Evaluation of N-[(Substituted 1H-pyrazol-3-yl)amino]-2-(4-methylphenyl)quinazolin-4(3H)-one Derivatives

Corresponding Author(s) : Sachin Kumar

Abstract

Keywords

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