(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-amino-5-(methoxycarbonyl)-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate | 1228231-80-8

• 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: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-amino-5-(methoxycarbonyl)-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS: 1228231-80-8
• 化学式: C₁₅H₂₀N₄O₉
• 分子量: 400.345
• InChiKey: WSFYWILHXVSCEX-PRULPYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.03
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  171.16
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  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-甲硫基苯硼酸 在 吡啶 、 copper acetate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以29%的产率得到methyl 2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-5-(4-methylsulfanylanilino)-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
• 作为产物：
  描述：

  3-azido-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-5-carboxylic acid methyl ester 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(3-amino-5-(methoxycarbonyl)-1H-1,2,4-triazol-1-yl)tetrahydrofuran-3,4-diyl diacetate
  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