Akbari Dilmaghani Karim, Nasuhi Pur Fazel, Mahammad Pour Majid, Mahammad Nejad Jafar
Department of Chemistry, Faculty of Science, Urmia University, Urmia, Iran.
Health Technology Incubator Center, Urmia University of Medical Sciences, Urmia, Iran.
Iran J Pharm Res. 2016 Fall;15(4):777-782.
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 by H NMR, C NMR and HRMS. The anomeric protons of nucleosides c were assigned to the doublet, confirming the β-configuration. The synthesized compounds were tested for their antimicrobial activity against (Gram-negetive) strain in 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 against 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 (c). The existence of -PhNO 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.
在碳酸钾存在下，用全乙酰化的β-吡喃糖基溴对1,3,4-恶二唑-2-硫酮进行糖基化反应。为增强其抗菌效果，对乙酰化硫代糖苷进行脱保护是必要的。通过氢核磁共振（H NMR）、碳核磁共振（C NMR）和高分辨质谱（HRMS）确定了核苷的结构。核苷c的端基质子被指定为双峰，证实了β-构型。与通常用于治疗此类感染的参考药物氨苄青霉素相比，测试了合成化合物对（革兰氏阴性）菌株的抗菌活性。合成化合物对测试的细菌菌株显示出不同的抑制圈。1,3,4-恶二唑-2-硫酮的硫代糖苷衍生物（c组）对ATCC 23055的活性比“母体”1,3,4-恶二唑-2-硫酮（a组）更高，证实了糖共轭与抗生素抗增殖活性增加之间的关系。最佳结果属于在其杂环核中带有2-呋喃基部分的核苷（c）。与其余合成化合物相比，a组及其相应糖衍生物结构中作为Ar的 -PhNO基团的存在降低了它们的抗菌活性。
