Abstract
2-Dimethylaminomethylene-1-benzosuberone 1 was coupled with diazotized aniline derivatives to afford a series of the hitherto unreported 2-arylazo-1-benzosuberones 3a-i. The tautomeric structure and the effect of substituents on the tautomeric form (s) of the products 3a-i were discussed. Similar coupling of the enaminone 1 with diazonium salts of heterocyclic amines gave the respective fused azolotriazino-benzosuberones. Some of the newly synthesized compounds showed potent antimicrobial, anti-HCV, antioxidant, antitumor (as topoisomerase I inhibitors), and antimicrobial activities.
MeSH terms
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Animals
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Antioxidants / chemical synthesis*
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Antioxidants / chemistry
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Antioxidants / pharmacology
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology
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Azo Compounds / chemical synthesis*
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Azo Compounds / chemistry
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Azo Compounds / pharmacology
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Biphenyl Compounds / metabolism
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Cricetinae
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Hepacivirus / growth & development
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Hydrazones / chemical synthesis*
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Hydrazones / chemistry
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Hydrazones / pharmacology
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Inhibitory Concentration 50
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Mice
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Microbial Sensitivity Tests
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Neoplasms, Experimental / drug therapy
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Picrates / metabolism
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SSPE Virus / growth & development
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Spectrophotometry, Infrared
Substances
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Anti-Bacterial Agents
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Antineoplastic Agents
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Antioxidants
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Antiviral Agents
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Azo Compounds
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Biphenyl Compounds
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Hydrazones
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Picrates
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1,1-diphenyl-2-picrylhydrazyl