Synthesis of Some Novel 2-{Pyrano[2,3-c]Pyrazoles-4-Ylidene}Malononitrile Fused with Pyrazole, Pyridine, Pyrimidine, Diazepine, Chromone, Pyrano[2,3-c]Pyrazole and Pyrano[2,3-d]Pyrimidine Systems as Anticancer Agents

An unexpected efficient basic catalyzed heterocyclization reactions were carried out to build blocks of potentially bioactive 2-{pyrano[2,3-c]pyrazoles-4-ylidene}malononitrile skeleton fused with pyrazole, pyridine, pyrimidine, diazepine, chromone, pyrano[2,3-c]pyrazole, and pyrano[2,3-d]pyrimidine...

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Bibliographic Details
Published in:Polycyclic aromatic compounds 2022-05, Vol.42 (5), p.2136-2150
Main Authors: Bakhotmah, Dina A., Ali, Tarik E., Assiri, Mohammed A., Yahia, Ibrahim S.
Format: Article
Language:English
Subjects:
Anticancer properties
Antitumor agents
Biocompatibility
Chemical reactions
chromone
Cytotoxicity
Malononitrile
nitrogen heterocycles
Nucleophiles
Pyranopyrazole
Pyrazole
Pyrazoles
Pyridines
Spectral methods
Toxicity
Tumor cell lines
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Summary:An unexpected efficient basic catalyzed heterocyclization reactions were carried out to build blocks of potentially bioactive 2-{pyrano[2,3-c]pyrazoles-4-ylidene}malononitrile skeleton fused with pyrazole, pyridine, pyrimidine, diazepine, chromone, pyrano[2,3-c]pyrazole, and pyrano[2,3-d]pyrimidine systems in novel molecular frames. The method depended on treatment of 6-amino-4-(4-oxo-4H-chromen-3-yl)-3-phenyl-1,4-dihydro-pyrano[2,3-c]pyrazole-5-carbonitrile (1) with different nitrogen and carbon nucleophiles in ethanolic sodium ethoxide. Possible mechanisms for the reactions were suggested. Elemental analyses and spectral techniques confirmed the structures of the isolated products. The compounds were evaluated for cytotoxic activities. Among the synthesized compounds, both 4 and 11 exhibited the most potent cytotoxicity against all used cancer cell lines.
ISSN:1040-6638
1563-5333
DOI:10.1080/10406638.2020.1827445