Original scientific paper

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

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 HAMED MANDOUR ; Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt
ESLAM REDA EL-SAWY ; Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt
MANAL SHAABAN EBAID ; Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt
SEHAM M. HASSAN ; Department of Drug Radiation Research, National Centre for Radiation Research and Technology, Cairo, Egypt

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-indolydine 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.

Keywords

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

Hrčak ID:

76601

URI

https://hrcak.srce.hr/76601

Publication date:

31.3.2012.

Article data in other languages: croatian

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