Premium
Synthesis, Antimicrobial Evaluation and Docking Study of Some Pyrazole Bearing [1, 2,4]Triazolo[3, 4‐b][1, 3,4]thiadiazole Derivatives
Author(s) -
Shingare Ramesh M.,
Patil Yogesh S.,
Sangshetti Jaiprakash N.,
Damale Manoj G.,
Rajani Dhanji P.,
Madje Balaji R.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800373
Subject(s) - chemistry , pyrazole , antimicrobial , stereochemistry , docking (animal) , antibacterial activity , 1,2,4 triazole , combinatorial chemistry , medicinal chemistry , organic chemistry , bacteria , medicine , nursing , biology , genetics
A novel series of pyrazole bearing[1, 2,4]triazolo[3, 4‐b][1, 3,4]thiadiazole derivatives ( 6 a‐l ) such as 3‐(5‐(3‐fluoro‐4‐methoxyphenyl)‐1 H ‐pyrazol‐3‐yl)‐6‐(2‐methoxyphenyl)‐[1, 2,4]triazolo[3, 4‐b][1, 3,4]thiadiazole were synthesized by cyclo‐condensation of 4‐amino‐5‐[5‐(3‐fluoro‐4‐methoxy‐phenyl)‐1 H ‐pyrazol‐3‐yl]‐4 H ‐[1, 2,4]triazole‐3‐thiol ( 5 ) with substituted benzoic/pyridinyl acids in phosphorus oxychloride giving good yields and purity. IR, 1 H NMR, 13 C NMR and LCMS/MS spectroscopy were used to characterise all the synthesized compounds. All the new derivatives were appraised for their antimicrobial activity, antifungal assay against C. Albicans, A. Niger and A. Clavatus along with Nystatin and Griseofulvin as standard drug and antibacterial assay against E. Coli, P. Aeruginosa, S. Aureus, S. Pyogenus along with Ampicillin as standard drug. Compounds ( 6 b ) and ( 6 j ) displayed excellent antifungal activity whereas compound ( 6 d ) and ( 6 e ) displayed excellent antibacterial activity. Molecular modelling and adsorption, distribution, metabolism and excretion‐toxicity (ADMET) prediction data clearly shows that 1,2,4‐triazolo[3, 4‐b][1, 3,4] thiadiazole derivatives ( 6 a‐l ) have potential to explore in the drug discovery pipeline as antifungal agents.