title: Regioselective synthesis, characterization and antimicrobial evaluation of S-glycosides and S,N-diglycosides of 1,2-Dihydro-5-(1H-indol-2-yl)-1,2,4-triazole-3-thione.
abstract: Glycosylation of 1,2-Dihydro-5-(1H-indol-2-yl)-1,2,4-triazole-3-thione with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was investigated in the presence of Et₃N and K₂CO₃ as acid scavengers. A regioselective S-glycosides were obtained by using Et₃N whereas, using K₂CO₃ gave a mixtures of two hybrids having two glycosidic bonds. The two products of each mixture were separated and characterized as S,N(1)- and S,N(2)-bis(glycosylated) derivatives. The structures of the newly synthesized compounds were elucidated by (1)H NMR, (13)C NMR, 2D NMR and mass spectra. The compounds were screened for their antibacterial and antifungal activities. Some compounds exhibited strong inhibition activity compared with the reference drugs (chloramphenicol and baneocin).
authors.affiliation: HEJ Research Institute for Chemistry, International Center for Chemical and Biological Sciences, Karachi University, Karachi, Pakistan. eelashry60@hotmail.com
authors.forename: El Sayed H
authors.initials: el SH
authors.lastname: El Ashry
authors.forename: El Sayed H
authors.initials: el SH
authors.lastname: El Tamany
authors.forename: Mohy El Din Abd
authors.initials: Mel D
authors.lastname: El Fattah
authors.forename: Ahmed T A
authors.initials: AT
authors.lastname: Boraei
authors.forename: Heba M
authors.initials: HM
authors.lastname: Abd El-Nabi
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C586652:1,2-dihydro-5-(1H-indol-2-yl)-1,2,4-triazole-3-thione; D000890:Anti-Infective Agents; D006027:Glycosides; D007211:Indoles; D014230:Triazoles
keywords: 1,2,4-Triazoles; Antimicrobial; Bis(glycosides); Glycosylation; Indolyltriazoles