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One‐Pot Multi‐Component Synthesis of 1,4‐Dihydropyridines Using Zn2+@KSF and Evaluating Their Antibacterial and Antioxidant Activities

New 5‐aryl‐10‐(4‐(4‐methoxyphenyl)thiazole‐2‐yl)‐9,10‐dihydropyrido[2,3‐d:5,6‐d′]dipyrimidinone‐2,4,6,8‐(1H,3H,5H,7H)‐tetraones 6a–d were synthesized through one‐pot four‐component reaction of aldehydes, barbituric acid, and thiazole using Zn2+@KSF under reflux condition. The key features of this reaction are: incorporating four heterocyclic rings, using a heterogeneous and efficient catalyst, high yield, and easy‐to‐setup reaction. The structure of the products was confirmed by FT‐IR, 1H NMR, and 13C NMR spectra. The antibacterial activities of compounds 6a–d were screened against Escherichia coli, Micrococcus luteus, Pseudomonas aeruginosa, and Staphylococcus aureus bacterial strains using the zone inhibition method. Also, the 2,2‐diphenyl‐2‐picrylhydrazyl (DPPH) radical scavenging activities of compounds 6a–d were evaluated. All compounds showed good antioxidant capacity in comparison to ascorbic acid. The IC50 values of the antioxidant activity were calculated. The proposed mechanism for antioxidant activity is discussed.

1,4‐Dihydropyridines were prepared from the reaction of barbituric acid, aldehydes, and thiazole in the presence of Zn2+@KSF. 10‐(4‐(4‐Methoxyphenyl)thiazole‐2‐yl)‐5‐(4‐nitrophenyl)‐9,10‐dihydropyrido[2,3‐d:5,6‐d′]dipyrimidone‐2,4,6,8‐(1H,3H,5H,7H)‐tetraone showed the best antibacterial and 10‐(4‐(4‐methoxyphenyl)thiazole‐2‐yl)‐5‐(2,4‐dichlorophenyl)‐9,10‐dihydropyrido[2,3‐d:5,6‐d′]dipyrimidone‐2,4,6,8‐(1H,3H,5H,7H)‐tetraone the highest antioxidant activity.

Autoren:   Nosrat O. Mahmoodi, Sahar Ramzanpour, Fateme Ghanbari Pirbasti
Journal:   Archiv der Pharmazie
Jahrgang:   2015
Seiten:   n/a
DOI:   10.1002/ardp.201400414
Erscheinungsdatum:   24.02.2015
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