Water mediated one-pot synthesis and biological evaluation of 1,2,3-triazolyl-1,4-dihydropyridine hybrids

Abstract

Design and synthesis of a new series of 1,2,3-triazolyl-1,4-dihydropyridine hybrids (5a-5l) have been accomplished by a one-pot multicomponent reaction of opropargyl salicylaldehyde/o-propargyl naphthaldehyde, b-keto compounds, ammonium acetate, and organic azides in short reaction times. In vitro antibacterial studies of the newly synthesized hybrids were investigated against four different human pathogens, viz. S. aureus, Proteus mirabilis, E. Coli, and K. Pnemonia, and the results were compared with that of the standard drug, tetracycline. Also, their anti-inflammatory activity was studied against bovine serum albumin (BSA) and compared with that of the reference drug, dichlofenac. Some of the hybrids show good antibacterial and antiinflammatory activities comparable with that of the reference drugs.Electronic supplementary material The online version of this article (

Novel 1,2,3-triazole-1,4-dihydropyridine-3,5-dicarbonitrile derivatives: synthesis and antibacterial evaluation

“…Comparatively, the derivative of 1,2,3-triazolyl-1,4-dihydropyridine having the propargyloxy group at the ortho position of the phenyl ring inhibited P. mirablis and K. pneumoniae with the MIC: 70 μg mL -1 . 30 The MIC value of compound 3i was 12.5 μg mL -1, which is twofold lower than Tetracycline (25 μg mL -1 ) against S. marcescens that is due to the methylene group attached to the triazole ring. The MIC value of compound 3f was found to be similar to Tetracycline against E. aerogenes.…”

“…In more, cyano, phenacyl, and benzyl derivatives of 1,2,3-triazolyl-1,4dihydropyridine hybrids were equal potent against Escherichia coli with MIC: 30 μg mL -1 a nd more potent against Klebsiella pneumoniae (MIC: 8 μg mL -1 compared to reference drug (MIC: 10 μg mL -1 ). 30 Some 1,2,3-triazole-linked β-lactam-bile acid conjugates showed moderate to good antifungal and antibacterial activity against Candida albicans, Candida neoformans, Fusarium oxysporum, Escherichia coli, and Staphylococcus aureus. 31 Between the series of 5-(4-methyl-1,2,3triazole)methyl oxazolidinones, the compound with substitution of the isopropylcarbonyl group at the piperazine C4 position was found to be potent against all tested 32 In one study, octyl triazole derivatives of the glycal derived novel tetrahydrofuran 1,2,3-triazoles displayed both antibacterial and antifungal activity at MIC: 12.5 μg mL -1 .…”

“…From the literature, it was found that cyano, phenacyl, and benzyl derivatives of 1,2,3-triazolyl-1,4-dihydropyridine hybrids were potent against Escherichia coli with MIC: 30 μg mL -1 . 30 Some fluorinated chalcone-triazole hybrids having -OMe functional group was also reported to be active against E. coli with MIC value of 0.0032 μmol mL -1 . 27 Compound 3e (MIC 200 μg mL -1 ) was also found to be more potent against S. flexneri compared to standard (MIC 400 μg mL -1 ).…”

Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesis

“…1,2,3-Triazole moiety is present in many available drugs [23] and lately 1,2,3-triazole hybrids are getting attention of many pharmacists partly due to their ease of formation by coupling two desired structural cores. There are several reports on the antibacterial activity of triazoles [24, 25]. Recently Zhang reported a comprehensive review on the recent advances of 1,2,3-triazole hybrids as potential anti-bacterial agents [26].…”

Green multicomponent synthesis of four different classes of six-membered N-containing and O-containing heterocycles catalyzed by an efficient chitosan-based magnetic bionanocomposite

“…In addition, they are biologically active molecules [18], with some exhibiting cytotoxicity [19], anti-inflammatory [20] or antibacterial [21] properties while others are calcium channel modulators [22].…”