methyl 3-amino-1-[2,3,5-tri-O-acetyl-β-D-ribofuranosyl]-1,2,4-triazole-5-carboxylate | 1228231-58-0

• 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 3-amino-1-[2,3,5-tri-O-acetyl-β-D-ribofuranosyl]-1,2,4-triazole-5-carboxylate
• 英文别名: methyl 5-anilino-2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxylate
• CAS: 1228231-58-0
• 化学式: C₂₁H₂₄N₄O₉
• 分子量: 476.443
• InChiKey: OESLTZOBXKZZCS-YWTNHNAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-1-[2,3,5-tri-O-acetyl-β-D-ribofuranosyl]-1,2,4-triazole-5-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以98%的产率得到5-anilino-2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-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 、 苯硼酸 在 吡啶 、 copper acetate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以44%的产率得到methyl 3-amino-1-[2,3,5-tri-O-acetyl-β-D-ribofuranosyl]-1,2,4-triazole-5-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

文献信息

• An Efficient Mixed-Ligand Pd Catalytic System to Promote CN Coupling for the Synthesis of N-Arylaminotriazole Nucleosides
  作者：Yuting Fan、Yi Xia、Jingjie Tang、Fabio Ziarelli、Fanqi Qu、Palma Rocchi、Juan L. Iovanna、Ling Peng

  DOI：10.1002/chem.201103918

  日期：2012.2.20

  Make it unique! A mixed‐ligand system of Pd/Synphos/Xantphos promotes effective CN coupling in the synthesis of various N‐arylaminotriazole and N‐arylaminopurine nucleoside analogues. This catalytic system is strikingly powerful and efficient, allowing for unparalleled substrate scope and high product yields as well as promotion of CCl bond activation for CN coupling (see scheme).

  使其独一无二！的Pd / Synphos /加入Xantphos的混合配体系统促进有效的C  N的各个的合成耦合Ñ -arylaminotriazole和Ñ -arylaminopurine核苷类似物。该催化体系是惊人地有力和有效的，从而允许无与伦比的底物范围和高的产物收率以及促进的C 对于C Cl键活化 N个耦合（参见方案）。
• Pd(dba)₂ vs Pd₂(dba)₃: An in-Depth Comparison of Catalytic Reactivity and Mechanism via Mixed-Ligand Promoted C–N and C–S Coupling Reactions
  作者：Mei Cong、Yuting Fan、Jean-Manuel Raimundo、Jingjie Tang、Ling Peng

  DOI：10.1021/ol501600k

  日期：2014.8.15

  With the help of mixed ligand catalytic systems, the analogous mechanisms behind the cognate performance by Pd(dba)2 and Pd2(dba)3 in catalyzing C-N and C-S coupling reactions were demonstrated. This information is instrumental in organic synthesis requiring Pd-catalyzed cross-coupling reactions and may also be valuable to other Pd-catalyzed transformations.
• N-Aryltriazole ribonucleosides with potent antiproliferative activity against drug-resistant pancreatic cancer
  作者：Yang Liu、Yi Xia、Yuting Fan、Alain Maggiani、Palma Rocchi、Fanqi Qu、Juan L. Iovanna、Ling Peng

  DOI：10.1016/j.bmcl.2010.02.104

  日期：2010.4

  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.