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Article

Synthesis and Anticonvulsant Activity of Novel 2- and 3-14-(Trisubstituted Pyridy1)-phenylaminol- and 2-[3- and 4-(Trisubstituted Pyridy1)-phenoxylquinoxaline Derivatives

by 1,*, 1 and 2
1
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, EGYPT
2
Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, EGYPT
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2003, 71(1), 9-18; https://doi.org/10.3797/scipharm.aut-03-02
Received: 16 August 2002 / Revised: 4 November 2002 / Accepted: 4 November 2002 / Published: 1 February 2003

Abstract

A series of novel quinoxaline derivatives linked to a pyridine moiety through phenylamino or phenoxy residue was synthesized and evaluated as candidate anticonvulsants. The synthesis was achieved through reaction of 2,3-dichloroquinoxaline (1) with an equimolar amount of 4-aminoacetophenone to give compound 2 which is considered as an important synthon for the construction of a pyridine ring via several synthetic routs. Some compounds were synthesized through formation of the intermediate α,β-unsaturated compounds which, in turn, were allowed to react with malononitrile to give the corresponding alkoxypyridines (8-17). Compounds 18-21 were synthesized by a one-pot simple reaction between 2, the appropriate aldehyde, and malononitrile in sodium alkoxide solution. Moreover, they can be synthesized through reaction of compound 2 and arylidenemalononitrile in sodium alkoxide. The phenoxy analogues were prepared by reaction of 1 with 4-hydroxyacetophenone or 3-hydroxybenzaldehyde to give 22 and 27, respectively. These compounds, in turn, were allowed to react with malononitrile and the proper carbonyl compound in presence of sodium alkoxide in a one-pot reaction technique to give the target compounds. Biological evaluation of the prepared compounds showed that some of them are potent anticonvulsant agents. The detailed synthesis, spectroscopic and biological data are reported.
Keywords: quinoxaline derivatives; alkoxypyridines; phenylamino and phenoxyquinoxalines; anticonvulsant activity quinoxaline derivatives; alkoxypyridines; phenylamino and phenoxyquinoxalines; anticonvulsant activity

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MDPI and ACS Style

Nasr, M.N.; Gineinaha, M.M.; Maarouf, A.R. Synthesis and Anticonvulsant Activity of Novel 2- and 3-14-(Trisubstituted Pyridy1)-phenylaminol- and 2-[3- and 4-(Trisubstituted Pyridy1)-phenoxylquinoxaline Derivatives. Sci. Pharm. 2003, 71, 9-18. https://doi.org/10.3797/scipharm.aut-03-02

AMA Style

Nasr MN, Gineinaha MM, Maarouf AR. Synthesis and Anticonvulsant Activity of Novel 2- and 3-14-(Trisubstituted Pyridy1)-phenylaminol- and 2-[3- and 4-(Trisubstituted Pyridy1)-phenoxylquinoxaline Derivatives. Scientia Pharmaceutica. 2003; 71(1):9-18. https://doi.org/10.3797/scipharm.aut-03-02

Chicago/Turabian Style

Nasr, Magda N., Magdy M. Gineinaha, and Azza R. Maarouf. 2003. "Synthesis and Anticonvulsant Activity of Novel 2- and 3-14-(Trisubstituted Pyridy1)-phenylaminol- and 2-[3- and 4-(Trisubstituted Pyridy1)-phenoxylquinoxaline Derivatives" Scientia Pharmaceutica 71, no. 1: 9-18. https://doi.org/10.3797/scipharm.aut-03-02

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