title: 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.
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.
authors.affiliation: Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt. ahmandour_z@yahoo.com
authors.forename: Adel Hamed
authors.initials: AH
authors.lastname: Mandour
authors.forename: Eslam Reda
authors.initials: ER
authors.lastname: El-Sawy
authors.forename: Manal Shaaban
authors.initials: MS
authors.lastname: Ebaid
authors.forename: Seham M
authors.initials: SM
authors.lastname: Hassan
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000927:Anticonvulsants / Q000138:chemical synthesis / Q000494:pharmacology; D016227:Benzoquinones; D002351:Carrageenan; D002626:Chemistry, Pharmaceutical; D004195:Disease Models, Animal; D004558:Electric Stimulation; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D005260:Female; D007249:Inflammation / Q000139:chemically induced / Q000517:prevention & control; D008297:Male; D051379:Mice; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000494:pharmacology*; D010146:Pain / Q000139:chemically induced / Q000517:prevention & control; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000254:growth & development; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D012640:Seizures / Q000209:etiology / Q000517:prevention & control; D013329:Structure-Activity Relationship; D013678:Technology, Pharmaceutical / Q000379:methods
chemical_list: D000700:Analgesics; D000900:Anti-Bacterial Agents; D000893:Anti-Inflammatory Agents; D000927:Anticonvulsants; D016227:Benzoquinones; D009570:Nitriles; D011720:Pyrazoles; C004532:quinone; D002351:Carrageenan