Design and synthesis of some thiazolotriazolyl esters as anti-inflammatory and analgesic agents

Abstract

In order to develop potent analgesic/antiinflammatory compounds with reduced ulcerogenic risk, a series of thiazolotriazolyl-carboxylic and acetic acid esters were synthesized and characterized by spectral and elementary analysis. All synthesized compounds were screened for in vivo anti-inflammatory activities in mice by carregeenan-induced paw edema model. The compounds showing 20% reduction in paw edema were also evaluated for their analgesic activities by acetic acid-induced writhing test and the gastric ulceration risk by determining the lipid peroxidation level in stomachs. Among the compounds tested, compounds 1, 4, 6, 7, 8, 1a, 2a, 3a, 4a, 7a, 2b, and 8b showed moderate-to-good anti-inflammatory activity at various doses in any of the measurement intervals. Compounds 7a, 2b, and 8b were the most actives of the series in analgesic activity test. Moreover, compounds 1, 4, and 8 were found to be safe in stomach in respect of free radical production.

Synthesis, Characterization, Antimicrobial Activity, and Docking Studies of New Triazolic Tripodal Ligands

“…In our case, it was obtained by N-hydroxymethylation of 1,2,4-triazole (98%, Sigma-Aldrich) as reported in literature. [20] Synthesis Synthesis of Methyl 1-Methyl-1H-1,2,4-triazole-3-carboxylate (2). A mixture of methyl 1H-1,2,4-triazole-3carboxylate (1; 5.00 g, 39.37 mmol) and potassium tert-butoxide (4.40 g, 39.37 mmol) in THF (350 ml) was stirred under reflux for 30 min.…”

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

“…The fusion of triazole and thiazole rings can lead to thiazolotriazoles with superior biological properties due to mutual influence of the pharmacophores centers present in the molecule. 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.…”

First Palladium‐Catalyzed Direct Regioselective C‐5 (Het)Arylation of Mono‐ or Disubstituted Thiazolo[3,2‐b][1,2,4]triazoles

“…Lately, the fusion of two heterocycles containing five atoms has attracted much attention. [4][5][6][7][8] The thiazolo [ crobial I, [4] antibacterial II, [5] G-quadruplex stabilizing III, [6] and anti-inflammatory IV [7,8] activities. [2] In connection with an ongoing project based on the development of efficient methodologies to generate original collections of small nitrogen-containing heterocycles, [3] we turned our attention to thiazolo [3,2-b] [1,2,4]triazole.…”

“…This highly attractive unit has seldom been described, despite the fact that some of its representatives have shown versatile biological activities (Figure 1). [4][5][6][7][8] The thiazolo[3,2-b]-[1,2,4]triazole core is found in structures possessing antimi-Scheme 1. Optimization of the C-H arylation.…”

“…Optimization of the C-H arylation. crobial I, [4] antibacterial II, [5] G-quadruplex stabilizing III, [6] and anti-inflammatory IV [7,8] activities.…”