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Iranian Journal of Pharmaceutical Research
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Akbari Dilmaghani, K., Nasuhipur, F., Mahammadpour, M., Mahammadnejad, J. (2016). Novel Oxadiazole Thioglycosides as Potential Anti- Acinetobacter Agents. Iranian Journal of Pharmaceutical Research, 15(4), 777-782. doi: 10.22037/ijpr.2016.1918
karim Akbari Dilmaghani; Fazel Nasuhipur; Majid Mahammadpour; jafar Mahammadnejad. "Novel Oxadiazole Thioglycosides as Potential Anti- Acinetobacter Agents". Iranian Journal of Pharmaceutical Research, 15, 4, 2016, 777-782. doi: 10.22037/ijpr.2016.1918
Akbari Dilmaghani, K., Nasuhipur, F., Mahammadpour, M., Mahammadnejad, J. (2016). 'Novel Oxadiazole Thioglycosides as Potential Anti- Acinetobacter Agents', Iranian Journal of Pharmaceutical Research, 15(4), pp. 777-782. doi: 10.22037/ijpr.2016.1918
Akbari Dilmaghani, K., Nasuhipur, F., Mahammadpour, M., Mahammadnejad, J. Novel Oxadiazole Thioglycosides as Potential Anti- Acinetobacter Agents. Iranian Journal of Pharmaceutical Research, 2016; 15(4): 777-782. doi: 10.22037/ijpr.2016.1918

Novel Oxadiazole Thioglycosides as Potential Anti- Acinetobacter Agents

Article 15, Volume 15, Issue 4, Autumn 2016, Page 777-782  XML PDF (312.77 K)
Document Type: Research article
DOI: 10.22037/ijpr.2016.1918
Authors
karim Akbari Dilmaghani1; Fazel Nasuhipur email 2; Majid Mahammadpour1; jafar Mahammadnejad1
1Department of Chemistry, Faculty of Science, Urmia University, Urmia, Iran
2Health Technology Incubator Center, Urmia University of Medical Science
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 structure of nucleosides were confirmed by 1H NMR, 13C NMR and HRMS. The anomeric protons of nucleosides c1–4 were assigned to the doublet, confirming the β-configuration. The synthesized compounds were tested for their antimicrobial activity against Acinetobacter calcoaceticus (Gram-negetive) strain in vitro in comparison with Ampicillin as 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 against Acinetobacter calcoaceticus ATCC 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 of m-PhNO2 group 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.
Keywords
1; 3; 4-Oxadiazole-2-thione; thioglycoside; nucleoside; Acinetobacter calcoaceticus; Antiproliferative activity
Main Subjects
Medicinal chemistry
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