Synthesis and anti-inflammatory evaluation of some new 3,6-disubstituted-1, 2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles bearing pyrazole moiety
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2012
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Abstract
In the present study, a new series of 3,6-disubstituted- 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles (4aj) have been synthesized by condensing 3-substituted-4-amino-5- mercapto-1,2,4-triazoles (1a-b) with various 3-substitutedpyrazole- 4-carboxylic acids (3a-e) in the presence ofPOCl3. The structures of newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13CNMR, and mass spectroscopic studies. Structure of the compound 4b was also confirmed by recording the single crystal X-ray structure. All the synthesized compounds were screened for their anti-inflammatory activities by carrageenan induced paw edema method. Anti-inflammatory screening indicated that, compounds 4d, 4e, and 4h were found to be biologically active whereas remaining compounds showed poor antiinflammatory activity. Also molecular docking studies were also performed for compounds which showed good antiinflammatory activity. © Springer Science+Business Media, LLC 2011.
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Keywords
1,2,4 triazole derivative, 1,3,4 thiadiazole derivative, 3 ethyl 6 ( 3 ( 2,4 dichlorophenyl) 1h pyrazol 4 yl)[ 1,2,4 ]triazolo[3,4 b][ 1,3,4 ]thiadiazole, 3 ethyl 6 ( 3 ( 4 chlorophenyl) 1h pyrazol 4 yl)[ 1,2,4 ]triazolo[3,4 b][ 1,3,4 ]thiadiazole, 3 ethyl 6 ( 3 ( 4 fluorophenyl) 1h pyrazol 4 yl)[ 1,2,4 ]triazolo[3,4 b][ 1,3,4 ]thiadazole, 3 ethyl 6 ( 3 ( 4 methoxyphenyl) 1h pyrazol 4 yl)[ 1,2,4]triazolo[3,4 b][ 1,3,4 ]thiadiazole, 3 ethyl 6 ( 3 phenyl 1h pyrazol 4 yl)[ 1,2,4 ]triazolo[3,4 b][ 1,3,4 ]thiadiazole, 3 propyl 6 ( 3 ( 2,4 dichlorophenyl) 1h pyrazol 4 yl)[ 1,2,4 ]triazolo[3,4 b][ 1,3,4]thiadiazole, 3 propyl 6 ( 3 ( 4 chlorophenyl) 1h pyrazol 4 yl0[ 1,2,4 ]triazolo[3,4 b][ 1,3,4 ]thiadiazole, 3 propyl 6 ( 3 ( 4 fluorophenyl) 1h pyrazol 4 yl)[ 1,2,4 ]triazolo[3,4 b][ 1,3,4 ]thiadiazole, 3 propyl 6 ( 3 ( 4 methoxyphenyl) 1h pyrazol 4 yl)[ 1,2,4 ]triazolo[3,4 b][ 1,3,4 ]thiadiazole, 3 propyl 6 ( 3 phenyl 1h pyrazol 4 yl)[ 1,2,4 ]triazolo[3,4 b][ 1,3,4 ]thiadiazole, antiinflammatory agent, carrageenan, diclofenac, pyrazole, pyrazole derivative, unclassified drug, animal experiment, antiinflammatory activity, article, carbon nuclear magnetic resonance, chemical analysis, chemical structure, computer model, controlled study, crystal structure, drug screening, drug synthesis, female, in vitro study, infrared spectroscopy, male, mass spectrometry, molecular docking, nonhuman, paw edema, proton nuclear magnetic resonance, rat, substitution reaction, X ray crystallography
Citation
Medicinal Chemistry Research, 2012, 21, 10, pp. 3272-3280