Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class.
In the present study, a series of new heterocyclic condensed systems with bridgehead nitrogen from the thiazolo[3,2-b][1,2,4]triazoles class was synthesized starting from some 4-(4-X-phenylsulfonyl)phenyl)-4H-1,2,4-triazole-3-thioles 1a-c (X=H, Cl, Br). The intermediates of S-alkylated 1,2,4-triazoles, 2-(5-(4-(4-X-phenylsulfonyl)phenyl)-2H-1,2,4-triazol-3-ylthio)-1-(4-fluorophenyl)ethanones 2a-c, were obtained by treatment of triazoles 1a-c with 2-bromo-4'-fluoroacetophenone. The 2-(4-(4-X-phenylsulfonyl)phenyl)-6-(4-fluorophenyl)thiazolo[3,2-b][1,2,4]triazoles 3a-c were obtained by cyclization of S-alkylated 1,2,4-triazoles 2a-c in sulfuric acid media, at 0 °C. For the synthesis of 2-(4-(4-X-phenylsulfonyl)phenyl)-5-(4-fluorobenzylidene)-thiazolo[3,2-b][1,2,4]triazol-6(5H)-ones 4a-c, the triazoles 1a-c were treated with 4-fluorobenzaldehyde, chloroacetic acid and anhydrous sodium acetate, in the presence of acetic acid and acetic anhydride. The structures of the newly synthesized compounds have been confirmed by elemental analysis and spectral methods (IR, 1H-NMR, 13C-NMR, MS). The antimicrobial activity of all new compounds has been screened against some bacteria and yeasts.
Organic Chemistry Department, Faculty of Pharmacy, "Carol Davila" University of Medicine and Pharmacy.
Stefania-Felicia
SF
Barbuceanu
Constantin
C
Draghici
Florica
F
Barbuceanu
Gabriela
G
Bancescu
Gabriel
G
Saramet
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000737:chemistry / Q000494:pharmacology*; D014230:Triazoles / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D006571:Heterocyclic Compounds; D013844:Thiazoles; D014230:Triazoles; D009584:Nitrogen