Synthesis and antimicrobial evaluation of some fused heterocyclic [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives

• Published in: European journal of medicinal chemistry 2010-12, Vol.45 (12), p.6139-6146
• Main Authors: Almajan, Gabriela Laura, Barbuceanu, Stefania-Felicia, Bancescu, Gabriela, Saramet, Ioana, Saramet, Gabriel, Draghici, Constantin
• Format: Article
• Language: English
• Subjects: [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Antimicrobial activity; Bacteria - drug effects; Biological and medical sciences; Cyclization; Diphenylsulfone moiety; Fungi - drug effects; General aspects; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Heterocyclic Compounds - pharmacology; Medical sciences; Molecular Structure; Pharmacology. Drug treatments; Stereoisomerism; Structure-Activity Relationship; Thiadiazoles - chemical synthesis; Thiadiazoles - chemistry; Thiadiazoles - pharmacology
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2010.10.007

A series of fused 1,2,4-triazoles with diphenylsulfone moiety are prepared utilizing 4-amino-5-[4-(4-X-phenylsulfonyl)phenyl]-4 H-1,2,4-triazole-3-thiol 1 (X = H, Br). The latter on reaction with aromatic isothiocyanate in DMF, aromatic acid in POCl 3 and CDI in dioxane gives five membered fused triazole derivatives 2a-c, 3a-c, 4a-g, 5a-g and 6a,b. The structures of newly synthesized compounds were confirmed on the basis of their elemental analysis and spectral data results (IR, 1H-and 13C NMR). New synthesized compounds were screened for their antimicrobial activities. The preliminary results revealed that some of the compounds exhibited promising antimicrobial activities. [Display omitted] ► Triazolo-thiadiazole system often presents antimicrobial activities.► A series of fused 1,2,4-triazoles with diphenylsulfone moiety are prepared utilizing 4-amino-5-[4-(4-X-phenylsulfonyl)phenyl]-4 H-1,2,4-triazole-3-thiol (X = H, Br).► The structures of the new derivatives were characterized using elemental analysis, IR, 1H-and 13C NMR.► The potential antimicrobial effects of new compounds were investigated and there are some promising results.