<abstract xml:lang="en" xmlns="http://www.w3.org/1999/xhtml"><p>Starting from <italic>N</italic>-substituted indole-3-carboxaldehydes (<bold>1a-g</bold>) a series of new 3-[(<italic>N</italic>-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-<italic>c</italic>)pyrazole-5-carbonitriles (<bold>3a-g</bold> and <bold>4a-g</bold>) have been synthesized <italic>via</italic> the acid catalyzed condensation reaction of <bold>1a-g</bold> with 3-amino-5-pyrazolone, followed by the reaction with arylidene malononitriles. A series of new 3,6-diamino-4-(<italic>N</italic>-substituted indol-3-yl)pyrano(2,3-<italic>c</italic>)pyrazole-5-carbonitriles (<bold>7a-g</bold>) have been prepared either <italic>via</italic> the base catalyzed condensation reaction of <bold>1a-g</bold> with 3-amino-5-pyrazolone to give <bold>6a-g</bold>, followed by the reaction with malononitrile or by the reaction of <italic>N</italic>-substituted-3-indolylidene malononitriles (<bold>5a-g</bold>) 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 <italic>Escherichia coli</italic> and <italic>Pseudomonas aeruginosa.</italic></p></abstract>

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.

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

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

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

Acta Pharmaceutica

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

Starting from N-substituted indole-3-carboxaldehydes (1a-g) a series of new 3-[(N-substituted...

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

Published Online: Apr 03, 2012

Page range: 15 - 30

DOI: https://doi.org/10.2478/v10007-012-0007-0

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

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