Synthesis and Evaluation of Curcuminoid Analogues as Antioxidant and Antibacterial Agents

• Published in: Molecules (Basel, Switzerland) Switzerland), 2017-06, Vol.22 (6), p.971
• Main Authors: Emam, Dalia R, Alhajoj, Ahmad M, Elattar, Khaled M, Kheder, Nabila A, Fadda, Ahmed A
• Format: Article
• Language: English
• Subjects: Acids; Aminopyridines - chemical synthesis; Aminopyridines - chemistry; Ampyrone - chemical synthesis; Ampyrone - chemistry; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; antibacterial activity; Antibacterial agents; Antibacterial materials; antioxidant activity; Antioxidants; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Ascorbic acid; Ascorbic Acid - pharmacology; Chloramphenicol; Chloramphenicol - pharmacology; Chloromycetin; Curcumin; Curcumin - analogs & derivatives; Curcumin - chemical synthesis; Curcumin - chemistry; Curcumin - pharmacology; Diazonium Compounds - chemical synthesis; Diazonium Compounds - chemistry; Gram-Negative Bacteria - drug effects; Gram-Negative Bacteria - pathogenicity; Gram-Positive Bacteria - drug effects; Gram-Positive Bacteria - pathogenicity; Humans; Hydrazines; Hydroxylamine; isoxazole; Microbial Sensitivity Tests; Molecular Structure; p-Toluidine; Pharmacy; pyrazole; Pyrazoles; Pyridines; pyrimidine; Salts; Sodium; Structure-Activity Relationship; Thiourea; Toluidine; Toluidines - chemical synthesis; Toluidines - chemistry; Urea
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules22060971

Diazocoupling reaction of curcumin with different diazonium salts of -toluidine, 2-aminopyridine, and 4-aminoantipyrine in pyridine yielded the arylhydrazones - . Arylhydrazone of -toluidine reacted with urea, thiourea, and guanidine nitrate to produce 5,6-dihydropyrimidines. Further reaction of with 2,3-diaminopyrdine in sodium ethoxide solution yielded 1 -pyrido[2,3- ][1,4]diazepine derivative. (2,5-dihydroisoxazole) is obtained from the reaction of with hydroxylamine hydrochloride, while its reactions with hydrazines afforded the respective 4,5-dihydro-1 -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.