methyl 2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-5-(4-methoxyanilino)-1,2,4-triazole-3-carboxylate | 1228231-63-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: methyl 2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-5-(4-methoxyanilino)-1,2,4-triazole-3-carboxylate
• CAS: 1228231-63-7
• 化学式: C₂₂H₂₆N₄O₁₀
• 分子量: 506.469
• InChiKey: UVJLVXZBABJLDD-SOAMZJECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  166
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-5-(4-methoxyanilino)-1,2,4-triazole-3-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以95%的产率得到2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(4-methoxyanilino)-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  N-Aryltriazole ribonucleosides with potent antiproliferative activity against drug-resistant pancreatic cancer

  摘要：

  Novel N-aryltriazole nucleosides were synthesized via Cu-mediated C-N cross-coupling reaction starting with 3-aminotriazole ribonucleoside and various boronic acids. Two of them exhibited potent apoptosis-related antiproliferative activity against the drug-resistant pancreatic cancer cell line MiaPaCa-2, with an increased potency compared to gemcitabine, the reference treatment for pancreatic cancer. A preliminary SAR study suggests that the appended N-aryl moiety and the substituent at its para-position, as well as the ribose sugar component, contribute considerably to the observed antiproliferative activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.104
• 作为产物：
  描述：

  (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-amino-5-(methoxycarbonyl)-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate 、 4-甲氧基苯硼酸 在 吡啶 、 copper acetate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以34%的产率得到methyl 2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-5-(4-methoxyanilino)-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  N-Aryltriazole ribonucleosides with potent antiproliferative activity against drug-resistant pancreatic cancer

  摘要：

  Novel N-aryltriazole nucleosides were synthesized via Cu-mediated C-N cross-coupling reaction starting with 3-aminotriazole ribonucleoside and various boronic acids. Two of them exhibited potent apoptosis-related antiproliferative activity against the drug-resistant pancreatic cancer cell line MiaPaCa-2, with an increased potency compared to gemcitabine, the reference treatment for pancreatic cancer. A preliminary SAR study suggests that the appended N-aryl moiety and the substituent at its para-position, as well as the ribose sugar component, contribute considerably to the observed antiproliferative activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.104