Abstract
Diazocoupling reaction of curcumin with different diazonium salts of p-toluidine, 2-aminopyridine, and 4-aminoantipyrine in pyridine yielded the arylhydrazones 2a-c. Arylhydrazone of p-toluidine reacted with urea, thiourea, and guanidine nitrate to produce 5,6-dihydropyrimidines. Further reaction of 2a with 2,3-diaminopyrdine in sodium ethoxide solution yielded 1H-pyrido[2,3-b][1,4]diazepine derivative. Bis(2,5-dihydroisoxazole) is obtained from the reaction of 2a with hydroxylamine hydrochloride, while its reactions with hydrazines afforded the respective 4,5-dihydro-1H-pyrazoles. The target compounds were evaluated as antioxidant and antibacterial agents. The tested compounds showed good to moderate activities compared to ascorbic acid and chloramphenicol, respectively.
Keywords:
antibacterial activity; antioxidant activity; curcumin; isoxazole; pyrazole; pyrimidine.
MeSH terms
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Aminopyridines / chemical synthesis
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Aminopyridines / chemistry
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Ampyrone / chemical synthesis
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Ampyrone / chemistry
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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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Antioxidants / chemical synthesis
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Antioxidants / chemistry
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Antioxidants / pharmacology*
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Ascorbic Acid / pharmacology
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Chloramphenicol / pharmacology
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Curcumin / analogs & derivatives
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Curcumin / chemical synthesis
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Curcumin / chemistry
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Curcumin / pharmacology*
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Diazonium Compounds / chemical synthesis
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Diazonium Compounds / chemistry
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Gram-Negative Bacteria / drug effects*
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Gram-Negative Bacteria / pathogenicity
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Gram-Positive Bacteria / drug effects*
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Gram-Positive Bacteria / pathogenicity
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Humans
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Microbial Sensitivity Tests
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Molecular Structure
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Structure-Activity Relationship
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Toluidines / chemical synthesis
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Toluidines / chemistry
Substances
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Aminopyridines
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Anti-Bacterial Agents
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Antioxidants
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Diazonium Compounds
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Toluidines
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Ampyrone
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Chloramphenicol
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4-toluidine
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Curcumin
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Ascorbic Acid
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alpha-aminopyridine