title: Novel Oxadiazole Thioglycosides as Potential Anti-AcinetobacterAgents.
abstract: The glycosylation of 1,3,4-oxadiazole-2-thiones has been performed with peracetylated β-pyranosyl bromide in the presence of potassium carbonate. Deprotection of acetylated thioglycosides was necessary for increasing their antibacterial effects. The structures of nucleosides were confirmed by1H NMR,13C NMR and HRMS. The anomeric protons of nucleosides c1-4were assigned to the doublet, confirming the β-configuration. The synthesized compounds were tested for their antimicrobial activity againstAcinetobacter calcoaceticus(Gram-negetive) strainin-vitroin comparison with Ampicillin as a reference drug which is normally used for treating such infections. The synthetic compounds showed different inhibition zones against tested bacterial strain. Thioglycoside derivatives of 1,3,4-oxadiazole-2-thiones (c set) were more active againstAcinetobacter calcoaceticusATCC 23055 than "parent" 1,3,4-oxadiazole-2-thiones (a set), confirming the relation between glyco-conjugation and increasing of antiproliferative activity of antibiotic agents. The best result belonged to nucleoside bearing 2-furyl moiety in its heterocyclic nucleus (c4). The existence ofm-PhNO2group as Ar in structures of a set and their corresponding sugar derivatives decreased the antibacterial activity of them in comparison with the rest of synthetic compounds.
authors.affiliation: Department of Chemistry, Faculty of Science, Urmia University, Urmia, Iran.
authors.forename: Karim
authors.initials: K
authors.lastname: Akbari Dilmaghani
authors.affiliation: Health Technology Incubator Center, Urmia University of Medical Sciences, Urmia, Iran.
authors.forename: Fazel
authors.initials: F
authors.lastname: Nasuhi Pur
authors.affiliation: Department of Chemistry, Faculty of Science, Urmia University, Urmia, Iran.
authors.forename: Majid
authors.initials: M
authors.lastname: Mahammad Pour
authors.affiliation: Department of Chemistry, Faculty of Science, Urmia University, Urmia, Iran.
authors.forename: Jafar
authors.initials: J
authors.lastname: Mahammad Nejad
keywords: 1; 3; 4-Oxadiazole-2-thione; Acinetobacter calcoaceticus; Antiproliferative activity; Nucleoside; Thioglycoside; in-vitro; β-Pyranosyl