Synthesis and anticonvulsant activity of Schiff’s bases of 3-{[2-({(E)-[(substituted) phenyl] methylidene} amino) ethyl] amino} quinoxalin-2(1H)-one

  • Ratnadeep V. Ghadage Department of Pharmaceutical Chemistry, Appasaheb Birnale College of Pharmacy, South Shivaji Nagar, Sangli 416416
  • Pramod J. Shirote Department of Pharmaceutical Chemistry, Appasaheb Birnale College of Pharmacy, South Shivaji Nagar, Sangli 416416
Keywords: Anti-covulsant, Microwave method, Phillips condensation, Quinoxaline, Schiff’s bases,

Abstract

In an effort to develop potent anticonvulsant agents, we have synthesized some novel schiffs bases of 3-{[2-({(E)-[substituted) phenyl] methylidene} amino) ethyl] amino} quinoxalin-2(1H)-one and evaluated for in vivo anticonvulsant activity. All the compounds were characterized by IR, 1H NMR data. This activity was carried out on pentylenetetrazole-induced seizure model. Compounds (IIIb) and (IIIc) Showed maximum time for straub tail and clonic convulsions. That means they possess good activity compared with standard. Animals treated with compounds (IIIb) and (IIIe) were recovered from this activity.

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Author Biography

Ratnadeep V. Ghadage, Department of Pharmaceutical Chemistry, Appasaheb Birnale College of Pharmacy, South Shivaji Nagar, Sangli 416416
Reasech student

References

Antoniottia S, Duach E. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines, Tetrahedron Lett. 2002; 43; 3971-73.

Cai JJ, Zou JP, Pan XQ, Zhang W. Gallium (III) triflate-catalyzed synthesis of quinoxaline derivatives. Tetrahedron Lett. 2008; 49; 7386-90.

Carta A, Paglietti G, Sanna P, Sechi L. Novel substituted quinoxaline 1,4-dioxides with in vitro antimycobacterial and anticandida activity. Eur J Med Chem. 2002; 37; 355-66.

Chung H, Jung O, Hong S, Chung KH, Lee SK, Ryu CK. Synthesis and biological evaluation of quinoxaline-5,8-diones that inhibit vascular smooth muscle cell proliferation, Bioorg Med Chem Lett. 2005; 15: 3380-84.

Faham AE, Massry1, Adel Amer AM, Gohar YM. A versatile synthetic route to chiral quinoxaline derivatives from amino acids precursors. Lett Pept Sci. 2002; 9: 49-54.

Harmenberg J, Wahren B, Bergman J, Lundblad L, Antiherpesvirus activity and mechanism of action of indolo-(2,3-b)quinoxaline and analogs. Antimicrob Agents Chemother. 1988; 32: 1720-24.

Hashem AA, Gouda MA, Badria FA. Synthesis of some new pyrimido [20,10:2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents. Eur J Med Chem. 2010; 45; 1976-81.

Jeon MK, Kim DS, La HJ, Gong YD. Solid-phase synthesis of quinoxaline derivatives using 6-amino-2,3-dichloroquinoxaline loaded on AMEBA resin. Tetrahedron Lett. 2005; 46: 4979-83.

Moarbess G, Masquefa CD, Bonnard V, Paniagua SG, Vidal JR, Pinguet F, Bonnet PA. In vitro and in vivo anti-tumoral activities of imidazo[1,2-a]quinoxaline, imidazo [1,5-a] quinoxaline, and pyrazolo[1,5-a] quinoxaline derivatives, Bioorg Med Chem. 2008; 16: 6601-10.

Refaat HM. Moneer AA, Khalil OM. Synthesis and antimicrobial activity of certain novel quinoxalines. Archives Pharm Res. 2004; 27: 1093-98.

Sridevi CH, Balaji K, Sudhakaran R. Synthesis of some phenyl pyrazolo benzimidazolo quinoxaline derivatives as potent antihistaminic agents. E-J Chem. 2010; 7: 234-38.

Urquiola C, Vieites M, Aguirre G, Solano B, Arrambide G. Improving anti-trypanosomal activity of 3-aminoquinoxaline-2-carbonitrile N1,N4-dioxide derivatives by complexation with vanadium. Bioorg Med Chem. 2006; 14: 5503-09.

Vicente E, Villar R, Burguete A, Solano B, Aldana I, Maddry JA, Franzblau SG, Cho SG Monge A, Robert C. Efficacy of quinoxaline-2-carboxylate 1,4-di-N-oxide derivatives in experimental tuberculosis. Antimicrob Agents Chemother. 2008; 52: 3321-26.

Xia H, Wang F, Yu KQ, Chen J, Bai D, Shen KX. Novel cyclophilin D inhibitors derived from quinoxaline exhibit highly inhibitory activity against rat mitochondrial swelling and Ca2+ uptake/release. Acta Pharmacologica Sinica 2005; 26: 1201-11.

Zarranz B, Jaso B, Lima LM, Aldana I, Monge A, Sauvain M. Antiplasmodial activity of 3-trifluoromethyl-2-carbonylquinoxaline di-N-oxide derivatives. Rev Bras Cienc Farm. 2006; 42: 1321-30.

Published
2011-11-13
How to Cite
Ghadage, R., & Shirote, P. (2011). Synthesis and anticonvulsant activity of Schiff’s bases of 3-{[2-({(E)-[(substituted) phenyl] methylidene} amino) ethyl] amino} quinoxalin-2(1H)-one. Bangladesh Journal of Pharmacology, 6(2), 92-99. https://doi.org/10.3329/bjp.v6i2.8671
Section
Research Articles