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One‐Pot Multi‐Component Synthesis of 1,4‐Dihydropyridines Using Zn 2+ @KSF and Evaluating Their Antibacterial and Antioxidant Activities
Author(s) -
Mahmoodi Nosrat O.,
Ramzanpour Sahar,
Ghanbari Pirbasti Fateme
Publication year - 2015
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201400414
Subject(s) - chemistry , micrococcus luteus , ascorbic acid , thiazole , antioxidant , dpph , antibacterial activity , carbon 13 nmr , organic chemistry , yield (engineering) , proton nmr , catalysis , nuclear chemistry , barbituric acid , escherichia coli , bacteria , biochemistry , food science , genetics , biology , gene , materials science , metallurgy
New 5‐aryl‐10‐(4‐(4‐methoxyphenyl)thiazole‐2‐yl)‐9,10‐dihydropyrido[2,3‐d:5,6‐d′]dipyrimidinone‐2,4,6,8‐(1 H ,3 H ,5 H ,7 H )‐tetraones 6a – d were synthesized through one‐pot four‐component reaction of aldehydes, barbituric acid, and thiazole using Zn 2+ @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, 1 H NMR, and 13 C 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 IC 50 values of the antioxidant activity were calculated. The proposed mechanism for antioxidant activity is discussed.