Synthesis and Antimicrobial Screening of Novel Thioglycosides and Acyclonucleoside Analogs Carrying 1,2,3-Triazole and 1,3,4-Oxadiazole Moieties

M. Aouad
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引用次数: 29

Abstract

ABSTRACT The solvent-free 1,3-dipolar cycloaddition reaction of dimethylacetylene dicarboxylate (1) with 2-chlorophenyl azide (2) afforded 1,2,3-triazole diester 3 that upon hydrazinolysis, furnished the corresponding bis-acid hydrazide 4. The treatment of compound 4 with carbon disulfide in a refluxing potassium hydroxide solution furnished the desired bis-1,3,4-oxadiazole-2-thione 5 tethered to a 1,2,3-triazole moiety. The respective SOx-glycosides 9–11 were obtained by glycosylation of bis-oxadiazole 5 with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide (6), 2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl bromide (7), and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride (8) in dry acetone in the presence of Et3N, which acted as a base. However, alkylation of 5 with halogeno-alkanol 12 or 13, chloroglycerol 14, bromoethers 20 or 21, and epichlohydrin 22 in the presence of K2CO3 in DMF yielded the corresponding acyclonucleoside analogs 16–18 and 23–25. The isopropylidenes 19 and acetyl derivatives 26–28 of the products were also prepared. The newly synthesized compounds were characterized by 1H NMR, 13C NMR, 2D NMR, and mass spectra. The compounds were screened for their antibacterial and antifungal activities. A number of the tested compounds exhibited significant antimicrobial activity compared to the reference drugs.
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含1,2,3-三唑和1,3,4-恶二唑基团的新型巯基糖苷和环核苷类似物的合成及抗菌筛选
摘要:二甲基乙炔二羧酸酯(1)与2-氯苯基叠氮化物(2)的无溶剂1,3-偶极环加成反应得到1,2,3-三唑二酯3,经肼解得到相应的二酸肼4。用二硫化碳在回流氢氧化钾溶液中处理化合物4,可得到与1,2,3-三唑基团相连的所需的双-1,3,4-恶二唑-2-硫酮5。分别用2,3,4,6-四-o -乙酰基-α-d-葡萄糖吡喃基溴(6)、2,3,4,6-四-o -乙酰基-α-d-半乳糖吡喃基溴(7)和2-乙酰氨基-3,4,6-三-o -乙酰基-2-脱氧-α-d-葡萄糖吡喃基氯(8)在干丙酮中以Et3N作为碱进行糖基化,得到了sox -糖苷9-11。然而,在DMF中,在K2CO3的存在下,5与卤代烷醇12或13、氯甘油14、溴醚20或21和环氧氯丙烷22烷基化,得到相应的环核苷类似物16-18和23-25。还制备了产物的异丙烯19和乙酰基衍生物26-28。通过1H NMR、13C NMR、2D NMR和质谱对新合成的化合物进行了表征。对化合物进行抗菌和抗真菌活性筛选。与对照药物相比,许多被测化合物显示出显著的抗菌活性。
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