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

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.

Malononitrile: A Versatile Active Methylene Group

“…Using cyclopentadienones: Andrew T. L. et al [33] have synthesized 6,6-dicyanofulvenes 49, 51 derived from monomeric and dimeric forms of cyclopentadienones 48, 50 with malononitrile 1 by using TiCl 4 …”

“…The malononitrile derivatives exhibits the synergistic toxicity in the toxic-dynamic and toxic-kinetic interactions with aldehyde components [1] . Some of the malononitrile derivatives shows the significant antimicrobial [2] such as antibacterial [3] and antifungal [4] [5] , anti-proliferative activities on human breast adenocarcinoma, ovarian adenocarcinoma and lymphoblastic leukemia cell [6] . They also acts as anticancer [7] , mollucicidal [8] , anti-inflammatory [9] and anti-oxidant [10] agents.…”

Synthesis, Antimicrobial Activity and Molecular Docking Study of Some New N-Benzyl and N-Benzoyl-3-Indolyl Heterocycles

“…Also, chalcones are wellknown intermediates for synthesizing various heterocyclic compounds like pyrazoline and pyrimidine derivatives [7,8]. In addition, indole derivatives which form potent pharmacodynamic nuclei have been reported to possess a wide variety of biological properties, viz., anti-inflammatory, anti-cancer and antimicrobial [9][10][11][12][13][14]. Encouraged by the above observations, and in continuation of our work on the preparation of new bioactive indole derivatives [7,[14][15][16], the present work is designed to synthesize new 3-indolylheterocycles starting from N-benzyl and N-benzoyl-1H-indole-3-carboxaldehyds and evaluating their antimicrobial activity.…”

Nano‐ZnO Catalyzed Green and Efficient One‐Pot Four‐Component Synthesis of Pyranopyrazoles

“…Pyrano [2,3-c]pyrazoles are the medicinally privileged compounds with a wide spectrum of biomedical and pharmaceutical applications [11]. Compound (a) of Figure 1 with pyrano[2,3-c]pyrazole scaffold in its structure has been documented as potential inhibitor of human Chk1 kinase [12].…”