New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation.
Some new 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(R)-2H-1,2,4-triazol-3(4H)-thiones 4a,b; 5a,b and 5-(4-(4-X-phenylsulfonyl)phenyl)-N-(R)-1,3,4-thiadiazol-2-amines 6a,b; 7a,b were obtained by cyclization of new N(1)-[4-(4-X-phenylsulfonyl)benzoyl]-N(4)-(R)-thiosemicarbazides 2a,b; 3a,b (X=H, Br). The 1,2,4-triazoles were synthesized by intramolecular cyclization of acylthiosemicarbazides, in basic media. On the other hand, 1,3,4-thiadiazoles were obtained from same acylthiosemicarbazides, in acidic media. These new intermediates from thiosemicarbazide class were afforded by the reaction of 4-(4-X-phenylsulfonyl)benzoic acids hydrazides (X=H, Br) 1a,b with 4-trifluoromethoxyphenyl or 3,4,5-trimethoxyphenyl isothiocyanate. The newly synthesized compounds were characterized by IR, (1)H NMR, (13)C NMR, MS and elemental analysis. All the new compounds were screened for their antimicrobial activity against some bacteria (Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 13061, Escherichia coli ATCC 25922, Enterobacter cloacae ATCC 49141, Acinetobacter baumannii ATCC 19606 and Pseudomonas aeruginosa ATCC 27853) and yeasts (Candida albicans ATCC 90028 and Candida parapsilosis ATCC 22019).
Organic Chemistry Department, Faculty of Pharmacy, Bucharest, Romania.
Stefania-Felicia
SF
Barbuceanu
Gabriel
G
Saramet
Gabriela Laura
GL
Almajan
Constantin
C
Draghici
Florica
F
Barbuceanu
Gabriela
G
Bancescu
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D005658:Fungi / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D009181:Mycoses / Q000188:drug therapy; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000890:Anti-Infective Agents; D013830:Thiadiazoles; D014230:Triazoles; C058949:1,3,4-thiadiazole; C045575:1,2,4-triazole