Synthesis, Characterization and Biological Studies of Some Bioactive Thiazolotriazole Derivatives

Abstract

The key precursor rac-2- (4-isobutylphenyl)ethyl-1,2,4-triazole-5-thione (3) was synthesized in good yield from Ibuprofen (1). One-pot three-component reactions of 3 with 5-aryl-furan-2-carboxaldehydes/substituted aromatic aldehydes and monochloroacetic acid in acetic acid in the presence of acetic anhydride and anhydrous sodium acetate afforded substituted thiazolo[3,2-b][1,2,4]triazole derivatives 4 and 5. The structures of the newly synthesized compounds were elucidated by elemental analyses and spectral data. The compounds were tested for their in-vitro antimicrobial activities.

Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

“…Thus, literature data indicate that numerous thiazolo [3,2-b] [1,2,4] triazoles derivatives have been reported to possess antibacterial, [3][4][5][6][7][8][9] antifungal, 3,[6][7][8][9] anti-inflammatory, 3,10,11) analgesic, 3,10) antiproliferative, 12) anticonvulsant 13) properties. Also, thiazolo [3,2-b][1,2,4] triazol-ones have been studied for their properties with respect to their biological activities including anti-inflammatory, [14][15][16][17] analgesic, 15,17) anticancer, [18][19][20] antibacterial, 21) antifungal 21) and anticonvulsant. 22) Another interesting class are diarylsulfones which are important intermediates in organic synthesis because of their chemical properties and biological activities being known especially as antibacterial agents.…”

Design and synthesis of novel quinazolinones conjugated ibuprofen, indole acetamide, or thioacetohydrazide as selective COX-2 inhibitors: anti-inflammatory, analgesic and anticancer activities

“…The compound (1) was prepared as reported before 22 . The hydrazides (2, 5, 9a, and 9b) were synthesised starting from their corresponding acids using previously reported procedures [23][24][25][26] . Compounds (10a, b-11a, b) were synthesised according to procedures previously described in the literatures 27,28 .…”

Thiazolotriazoles As Anti-infectives: Design, Synthesis, Biological Evaluation and In Silico Studies

“…N -Heterocycles such as thiazole and triazole are privileged scaffolds in drug discovery programs, with diverse pharmacological activity. , Similarly, thiazole or triazole fused with other heterocycles have been investigated against various diseases. , The condensed heterocycle of thiazole and triazole is termed as thiazolotriazole and exists in three isomeric forms: thiazolo­[2,3- c ]­[1,2,4]­triazole, thiazolo­[3,2- b ]­[1,2,4]­triazole and isothiazolo­[3,2- c ]­[1,2,4]­triazole . A wide range of pharmacological activities like anticancer, − antimicrobial, − anti-inflammatory, analgesic, antidiuretic, and COX 2 inhibition were reported for thiazolotriazoles; major efforts in research were focused on antimicrobial drug design, with the [3,2- b ] ring system being widely investigated when compared to the [2,3- c ] ring system (Figure ); however, the proven or suggested mode of action or drug targets are not well established for any of the thiazolotriazole-based antimicrobials. In antitubercular drug research, the thiazolotriazoles have not been widely investigated (Figure ).…”