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Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

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Synthesis and potential biological activity of some novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles

Adel Mandour1 / Eslam El-Sawy1 / Manal Ebaid1 / Seham Hassan1

Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt1

Department of Drug Radiation Research, National Centre for Radiation Research and Technology, Cairo, Egypt2

This content is open access.

Citation Information: Acta Pharmaceutica. Volume 62, Issue 1, Pages 15–30, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: 10.2478/v10007-012-0007-0, April 2012

Publication History

Published Online:
2012-04-03

Synthesis and potential biological activity of some novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles

Starting from N-substituted indole-3-carboxaldehydes (1a-g) a series of new 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles (3a-g and 4a-g) have been synthesized via the acid catalyzed condensation reaction of 1a-g with 3-amino-5-pyrazolone, followed by the reaction with arylidene malononitriles. A series of new 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles (7a-g) have been prepared either via the base catalyzed condensation reaction of 1a-g with 3-amino-5-pyrazolone to give 6a-g, followed by the reaction with malononitrile or by the reaction of N-substituted-3-indolylidene malononitriles (5a-g) with 3-amino-5-pyrazolone. According to the obtained results, the newly synthesized compounds possess significant anti-inflammatory, analgesic and anticonvulsant activities. The anticonvulsant potency of certain tested compounds was more pronounced than both anti-inflammatory and analgesic activities. Moreover, most of the newly synthesized compounds possess potential antimicrobial activity against Escherichia coli and Pseudomonas aeruginosa.

Sinteza i potencijalno biološko djelovanje novih 3-((N-supstituiranih indol-3-il)metilenamino)-6-amino-4-aril-pirano(2,3-c)pirazol-5-karbonitrila i 3,6-diamino-4-(N-supstituiranih indol-3-il)pirano(2,3-c)pirazol-5-karbonitrila

U radu se opisuje sinteza novih 3-[N-supstituiranih indol-3-il)metilenamino]6-amino-4-aril-pirano(2,3-c) pirazol-5-karbonitrila (3a-g i 4a-g) kiselo-kataliziranom kondenzacijom N-supstituiranih indol-3-karboksaldehida (1a-g) s 3-amino-5-pirazolonom iza koje slijedi reakcija s ariliden malononitrilom. Serija novih 3,6-diamino-4-(N-supstituiranih indol-3-il)pirano(2,3-c)pirazol-5-karbonitrila (7a-g) sintetizirana je reakcijom malononitrila s produktima 6a-g, koji su pripravljeni bazno-kataliziranom kondenzacijom 1a-g s 3-amino-5-pirazolonom. Neki spojevi iz serije 7a-g dobiveni su reakcijom N-supstituiranih 3-indolidin malononitrila (5a-g) s 3-amino-5-pirazolonom. Novosintetizirani spojevi imaju značajno protuupalno, analgetsko i antikonvulzivno djelovanje. Antikonvulzivno djelovanje pojedinih testiranih spojeva bilo je jače izraženo nego protuupalno i analgetsko djelovanje. Većina ispitivanih spojeva pokazuje antimikrobno djelovanje na Escherichia coli i Pseudomonas aeruginosa.

Keywords: indole; pyrano(2,3-c)pyrazole; anti-inflammatory; analgesic; anticonvulsant; antimicrobial activity

Keywords: indol; pirano(2,3-c)pirazol; protuupalno; analgetsko; antikonvulzivno; antimikrobno djelovanje

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