Karabasanagouda, T.Vasudeva Adhikari, A.V.Shetty, N.S.2026-02-052007European Journal of Medicinal Chemistry, 2007, 42, 4, pp. 521-5292235234https://doi.org/10.1016/j.ejmech.2006.10.010https://idr.nitk.ac.in/handle/123456789/27817Thirty one new 6-aryl-3-{(4-substituted phenoxy) methyl}-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles (6a-s) and 6-aryl-3-{(4-substituted phenoxy methyl}-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (7a-l) have been synthesized from 4-thioalkyl phenols (1a-b) through a multi-step reaction sequence. Compounds 1a-b reacted with ethyl chloroacetate in presence of acetone and potassium carbonate to give ethyl [4-(thioalkyl) phenoxy] acetates (2a-b). Further, 2a was oxidized to [4-(methyl sulphonyl) phenoxy] acetate (2c) using hydrogen peroxide in acetic acid. Reactions of (2a-c) with hydrazine hydrate in alcoholic medium furnished 2-[4-thiosubstituted phenoxy] acetohydrazides (3a-b) and 2-[4-methyl sulphonyl phenoxy] acetohydrazide (3c) which on treatment with carbon disulphide and methanolic potassium hydroxide yielded corresponding potassium dithiocarbazates (4a-c). They were then converted to 4-amino-5-{(4-thioalkyl phenoxy) methyl}-4H-1,2,4-triazole-3-thiols (5a-b) and 4-amino-5-{(4-methyl sulphonyl phenoxy) methyl}-4H-1,2,4-triazole-3-thiol (5c) by refluxing them with aqueous hydrazine hydrate. The title compounds 6a-s were prepared by condensing 5a-c with various aromatic carboxylic acids in presence of phosphorus oxychloride. The intermediates 5a-c, on condensation with various substituted phenacyl bromides afforded a series of title compounds (7a-l). The structures of new compounds 2a-7l were established on the basis of their elemental analysis, IR, 1H NMR, 13C NMR and mass spectral data. All the title compounds were subjected to in vitro antibacterial testing against four pathogenic strains and antifungal screening against three fungi. Preliminary results indicate that some of them exhibited promising activities and they deserve more consideration as potential antimicrobials. © 2006 Elsevier Masson SAS. All rights reserved.1,2,4 triazolo[3,4 b] 1,3,4 thiadiazine1,2,4 triazolo[3,4 b] 1,3,4 thiadizole1,3,4 thiadiazine derivative1,3,4 thiadiazole derivative2 [4 methylsulfonylphenoxy]acetohydrazide2 [4 thiophenoxy]acetohydrazide derivative3 [(4 methylsulfonylphenoxy)methyl] 1,2,4 triazolo[3,4 b] 1,3,4 thiadiazine3 [(4 methylsulfonylphenoxy)methyl] 1,2,4 triazolo[3,4 b] 1,3,4 thiadiazole3 [(4 thiophenoxy)methyl] 1,2,4 triazolo[3,4 b] 1,3,4 thiadiazine3 [(4 thiophenoxyl)methyl] 1,2,4 triazolo[3,4 b] 1,3,4 thiadiazole4 amino 5 [(4 methylsulfonylphenoxy)methyl] 4h 1,2,4 triazole 3 thiol4 amino 5 [(4 thiophenoxy)methyl] 4h 1,2,4 triazole 3 thiol derivative4 bromophenacyl bromide[4 (methylsulfonyl)phenoxy]acetateacetic acidacetonearomatic carboxylic acidcarbon disulfidechloroacetic acidethyl (4 thiophenoxyl)acetate derivativehydrazinehydrogen peroxidephenol derivativepotassium carbonatepotassium dithiocarbazate derivativepotassium hydroxideunclassified drugantibacterial activityarticlecarbon nuclear magnetic resonancechemical reactioncontrolled studydrug screeningdrug synthesisinfrared spectroscopyminimum inhibitory concentrationnonhumanpolymerizationproton nuclear magnetic resonanceAnti-Bacterial AgentsAntifungal AgentsBacteriaFungiMicrobial Sensitivity TestsMolecular StructureThiadiazinesThiadiazoles