1-(4-ethoxycarbonyl-5-ethylpropiolate-[1,2,3]triazol-1-yl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose | 1402406-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-ethoxycarbonyl-5-ethylpropiolate-[1,2,3]triazol-1-yl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
• 英文别名: 1-deoxy-1-(5-(3-ethoxy-3-oxoprop-1-yn-1-yl)-4-(ethoxycarbonyl)-1H-1,2,3-triazol-1-yl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose；ethyl 5-(3-ethoxy-3-oxoprop-1-ynyl)-1-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]triazole-4-carboxylate
• CAS: 1402406-35-2
• 化学式: C₂₄H₂₉N₃O₁₃
• 分子量: 567.507
• InChiKey: AESDMLDWJUAOPZ-LDBVRRDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  198
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  丙炔酸乙酯 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 双氧水 、 copper(l) cyanide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到1-(4-ethoxycarbonyl-5-ethylpropiolate-[1,2,3]triazol-1-yl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  In Vitro and in Vivo Evaluation of Fully Substituted (5-(3-Ethoxy-3-oxopropynyl)-4-(ethoxycarbonyl)-1,2,3-triazolyl-glycosides as Original Nucleoside Analogues to Circumvent Resistance in Myeloid Malignancies

  摘要：

  yy A series of nucleoside analogues bearing a 1,4,5-trisubstituted-1,2,3-triazole aglycone was synthesized using a straightforward click/electrophilic addition or click/oxidative coupling tandem procedures. SAR analysis, using cell culture assays, led to the discovery of a series of compounds belonging to the 5-alkynyl-1,2,3-triazole family that exhibits potent antileukemic effects on several hematologic malignancies including chronic myeloid leukemia (CML) and myelodysplastic syndromes (MDS) either sensitive or resistant to their respective therapy. Compound 4a also proved efficient in-vivo on mice xenografted with SKM1-R MDS cell line. Additionally, some insights in its mode of action revealed that this compound induced cell death by caspase and autophagy induction.

  DOI：

  10.1021/acs.jmedchem.6b01803