Search

In an endeavor to invent new antimalarial and antimicrobial agents, a series of coumarin bound 1,4-disubstituted 1,2,3-triazoles was synthesized through Cu(I)-promoted click reaction between coumarin bound terminal alkynes, that is, 4/7-(prop-2-yn-1-yloxy)-2H-chromen-2-one and 2-azido-N-arylpropanamides. The synthesized 1,2,3-triazoles were characterized by FTIR,1H NMR,13C NMR, and HRMS techniques and were assessed for in vitro antimalarial activity against Plasmodium falciparum as well as in vitro antimicrobial activity against four bacterial strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae) and two fungal strains (Candida albicans, Aspergillus niger). Compound 7o [(N-(4-fluorophenyl)-2-(4-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)propanamide)] displayed better activity against P. falciparum while compound 7y [(N-(3-nitrophenyl)-2-(4-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)propanamide)] displayed excellent activity against all the tested bacterial and fungal strains, amongst the synthesized triazoles. Also, the molecular docking studies of the most potent compounds against DNA gyrase (S. aureus) were also performed to have an insight on binding interactions. [ABSTRACT FROM AUTHOR]

A series of quinoline-thiazole appended 1,4-disubstituted 1,2,3-triazole were synthesized by performing Cu(I) catalyzed 1,3-dipolar cycloaddition reaction ("Click" reaction) and fully characterized by various spectral techniques like FTIR, NMR and HRMS. These compounds were evaluated for in vitro antimalarial activity against plasmodium falciparum. All the compounds (7a–7y) exhibited moderate to good activity in comparison to standard drug Quinine. Compound 7r (IC50 0.19 µg/mL) displayed appreciable activity comparable to Quinine (IC50 0.268 µg/mL). Further antimicrobial screening of the synthesized substituted triazoles were also carried out against two gram (+) bacteria (Staphylococcus aureus, Bacillus subtilis), two gram (–) bacteria (Escherichia coli, Klebsiella pneumonia) and two fungi (Candida albicans, Aspergillus niger). Results revealed that compound 7r reflected promising antimicrobial activity among the synthesized library of molecules. Molecular docking studies of broadly active antimalarial disubstituted triazoles 7m and 7r were explored in the active site of enzyme dihydroorotate dehydrogenase (DHODH) to have the probable mode of action. [ABSTRACT FROM AUTHOR]

A series of twenty one sulfonamide tethered 1,4-disubstituted 1,2,3-triazoles was synthesized in good yields through a facile expeditious click synthetic protocol involving Cu(I) mediated cyclization between terminal alkynes containing ester linkage and 4-azidobenzenesulfonamide. All the synthesized triazoles were characterized using FTIR,1H NMR,13C NMR and HRMS techniques. Synthesized compounds were also evaluated for in vitro antibacterial activity against two Gram positive bacteria (Staphylococcus aureus, Bacillus subtilis) and two Gram negative bacteria (Klebsiella pneumoniae, Escherichia coli) by serial dilution method. In the series, compound 6 l, 3-(1-(4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)propyl 4-bromobenzoate with Minimum Inhibitory Concentration (MIC) 0.0134 µmol/mL exhibited appreciable antibacterial activity against all bacterial strains comparable with standard drug Ciprofloxacin (MIC 0.0189 µmol/mL). Further, molecular docking study was also performed to gain insight for binding interactions with dihydropteroate synthase enzyme. [ABSTRACT FROM AUTHOR]

A series of amide tagged 1,4-disubstituted 1,2,3-triazole has been designed and synthesized in good yield through Cu (I) catalyzed click chemistry strategy. The synthesized triazoles were characterized by various spectral techniques like FT-IR, 1H NMR, 13C NMR, and high-resolution mass spectrometery. The synthesized amide-tagged disubstituted triazoles were assessed for in vitro antimicrobial activity against two Gram-positive bacteria- Staphylococcus aureus, Bacillus subtilis; two Gram-negative bacteria- Escherichia coli, Klebsiella pneumonia and two fungi-Candida albicans, Aspergillus niger. Most of the synthesized compounds displayed good activity, among these, compound 6 m, 4-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide and compound 6t, 2-(4-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide with MIC values 0.020 and 0.017 µmol/mL respectively revealed appreciable efficacy against tested microbial strains. Further, molecular docking study also disclosed that docked compounds 6 m and 6t bound efficiently with the active site of receptor S. aureus DNA gyrase. [ABSTRACT FROM AUTHOR]

In the present study, a series of sulfonamide bridged 1,4-disubstituted 1,2,3-triazoles have been synthesized in good yield via click reaction between sulfonamide linked terminal alkynes and in situ prepared 2/3/4-azidobenzenesulfonamides. The synthesized triazoles were characterized by FTIR, 1H NMR, 13C NMR, and HRMS techniques. Further, all the synthesized compounds were assessed for in vitro antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumonia. It has been observed that some of the synthesized triazoles possess appreciable efficacy against the bacterial strains used. Particularly, compound 4-bromo-N-((1-(4-(sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methyl)benzenesulfonamide 6l (MIC = 0.132 µmol/mL) revealed significant antibacterial activity against B. subtilis, E. coli, and K. pneumonia. Further, the molecular docking study of the above potent compound was also performed in the active site of the enzyme dihydropteroate synthase to have the possible mode of action. [ABSTRACT FROM AUTHOR]

A series of Piperazine containing substituted 1,2,3-triazoles with amide linkage have been designed and synthesized via click reaction between 1-aryl-4-(prop-2-yn-1-yl)piperazines and N-aralkyl-2-bromoacetamides. All synthesized triazoles were explicated by various spectral techniques like 1H NMR, 13C NMR, Fourier transform infrared and high-resolution mass spectrometry. The synthesized compounds were screened for in vitro antimicrobial activity against different strains viz. Bacillus subtilis, Staphylococcus epidermidis, Escherichia coli, Pseudomonas aeroginosa, Candida albicans, Aspergillus niger reflecting moderate to good activity, while compound 7u displayed appreciable activity with minimum inhibitory concentration 0.0248 µmol/mL. Molecular docking studies of the potent compounds 7r and 7u were also explored. The ADME (Absorption, Distribution, Metabolism and Excretion) studies of the synthesized triazoles were also carried out to prospect drug likes properties. [ABSTRACT FROM AUTHOR]

The present paper elicits a marvelous synthesis of a series of sulfonamide containing 1,4-disubstituted 1,2,3-triazoles through click reaction of terminal alkynes with aromatic azides. The synthesized triazoles were characterized by FTIR, 1H NMR,13C NMR and HRMS techniques. Further, the structures of synthesized compounds 6u (CCDC 1954932) and 6z3 (CCDC 1954931) were also confirmed by X-ray crystallography. The synthesized triazoles were evaluated for in vitro antibacterial activity against S. aureus, B.subtilis, E. coli and K. pneumoniae by serial dilution method. Among the series, compound 4-bromo-N-(2-(1-(4-bromophenyl)-1H-1,2,3-triazol-4-yl)propan-2-yl)benzenesulfonamide, 6z4 (MIC = 0.025 µM/mL) and 4-bromo-N-(2-(1-(naphthalen-1-yl)-1H-1,2,3-triazol-4-yl)propan-2-yl)benzenesulfonamide 6z6 (MIC = 0.027 µM/mL) exhibited the appreciable antibacterial activity against Staphylococcus aureus and Bacillus subtilis. Further, the molecular docking studies of above potent analogs with dihydropteroate synthase was performed to have an insight for binding interactions. Synthesized molecules were also explored for antioxidant activity, reflecting compound 6m as better radical scavenging agent with IC50 value of 1.96 µM/mL. [ABSTRACT FROM AUTHOR]

A series of twenty seven ether linked 1,4-disubstituted 1,2,3-triazoles was assessed for in vitro antimalarial activity against Plasmodium falciparum, while antibacterial activity against Bacillus cereus, Escherichia coli and Staphylococcus aureus. Biological evaluation of synthesized triazoles revealed moderate to good antimalarial and antibacterial activity against the tested strains. Molecular docking study has also been investigated for most active compound 19, that disclosed binding to the active site of E. coli DNA Gyrase. [ABSTRACT FROM AUTHOR]