O-{[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]methyl}-3-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]propanoate | 1187182-89-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-{[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]methyl}-3-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]propanoate
• 英文别名: [1-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]triazol-4-yl]methyl 3-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]propanoate
• CAS: 1187182-89-3
• 化学式: C₂₈H₃₀ClN₅O₁₂
• 分子量: 664.025
• InChiKey: NQKWCRFHPDFHAT-ZKPBLSLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  210
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  3-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]propionic acid prop-2-ynyl ester 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 copper diacetate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.0h， 以66%的产率得到O-{[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]methyl}-3-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]propanoate
  参考文献：
  名称：

  Synthesis and cytotoxic profile of glycosyl–triazole linked to 1,2,4-oxadiazole moiety at C-5 through a straight-chain carbon and oxygen atoms

  摘要：

  The convergent synthesis of an unusual (but simple) class of compounds 5a-g has been achieved by the copper-catalyzed [3 + 2] cycloaddition reaction of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide 4 with propynyl 3-[3-(aryl)-1,2,4-oxadiazol-5-yl] propionates 3a-g. The formerly known azide 4 has been prepared according to the literature procedure; however, the synthesis of esters 3a-g is being reported for the first time. The infrared as well as H-1 NMR spectra of all new products are in agreement with their proposed structures. By carrying out the nOe experiment of one of the final compounds 5a, we have been able to establish that only the 1,4-regioisomers have been formed in the cycloaddition reaction. All final products presented weak cytotoxic activity, but 5e and 5g had somewhat better behaviour showing 22-25% cell growth inhibition against two cell strains: NCl-H-292 (lung carcinoma) and HEp-2 (larynx carcinoma). (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.002