methyl 2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-5-[2-[4-(trifluoromethyl)phenyl]ethynyl]-1,2,4-triazole-3-carboxylate | 1190605-25-4

• 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-[2-[4-(trifluoromethyl)phenyl]ethynyl]-1,2,4-triazole-3-carboxylate
• CAS: 1190605-25-4
• 化学式: C₂₄H₂₂F₃N₃O₉
• 分子量: 553.449
• InChiKey: WDJLOFOKTDBBJK-JWUVWSEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  14

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-[2-[4-(trifluoromethyl)phenyl]ethynyl]-1,2,4-triazole-3-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以74%的产率得到3-(4-trifluoromethylphenyl-ethynyl)-1-(β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylic acid amide
  参考文献：
  名称：

  Novel Triazole Ribonucleoside Down-Regulates Heat Shock Protein 27 and Induces Potent Anticancer Activity on Drug-Resistant Pancreatic Cancer

  摘要：

  A series of novel 3-arylethynyltriazolyl ribonucleosides were synthesized and assessed for their anticancer activity on the drug-resistant pancreatic cancer cell line MiaPaCa-2. Among them, one compound exhibited potent apoptosis-inducing properties and anticancer activity against the pancreatic cancer model MiaPaCa-2 both in vitro and in vivo with no adverse effects. This compound did not inhibit DNA synthesis and therefore does not resemble the clinical drug gemcitabine. It did, however, significantly down-regulate the expression of heat shock protein 27 (Hsp27), a small molecular chaperone playing an important role in drug resistance and highly expressed in drug-resistant cancer forms, and thus represents the first small molecular anticancer lead with such a mode of action.

  DOI：

  10.1021/jm900960v
• 作为产物：
  描述：

  4-乙炔基-α,α,α-三氟甲苯 、 3-bromo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-5-carboxylic acid methyl ester 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以58%的产率得到methyl 2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-5-[2-[4-(trifluoromethyl)phenyl]ethynyl]-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Novel Triazole Ribonucleoside Down-Regulates Heat Shock Protein 27 and Induces Potent Anticancer Activity on Drug-Resistant Pancreatic Cancer

  摘要：

  A series of novel 3-arylethynyltriazolyl ribonucleosides were synthesized and assessed for their anticancer activity on the drug-resistant pancreatic cancer cell line MiaPaCa-2. Among them, one compound exhibited potent apoptosis-inducing properties and anticancer activity against the pancreatic cancer model MiaPaCa-2 both in vitro and in vivo with no adverse effects. This compound did not inhibit DNA synthesis and therefore does not resemble the clinical drug gemcitabine. It did, however, significantly down-regulate the expression of heat shock protein 27 (Hsp27), a small molecular chaperone playing an important role in drug resistance and highly expressed in drug-resistant cancer forms, and thus represents the first small molecular anticancer lead with such a mode of action.

  DOI：

  10.1021/jm900960v

文献信息

• Novel Triazole Ribonucleoside Down-Regulates Heat Shock Protein 27 and Induces Potent Anticancer Activity on Drug-Resistant Pancreatic Cancer
  作者：Yi Xia、Yang Liu、Jinqiao Wan、Menghua Wang、Palma Rocchi、Fanqi Qu、Juan L. Iovanna、Ling Peng

  DOI：10.1021/jm900960v

  日期：2009.10.8

  A series of novel 3-arylethynyltriazolyl ribonucleosides were synthesized and assessed for their anticancer activity on the drug-resistant pancreatic cancer cell line MiaPaCa-2. Among them, one compound exhibited potent apoptosis-inducing properties and anticancer activity against the pancreatic cancer model MiaPaCa-2 both in vitro and in vivo with no adverse effects. This compound did not inhibit DNA synthesis and therefore does not resemble the clinical drug gemcitabine. It did, however, significantly down-regulate the expression of heat shock protein 27 (Hsp27), a small molecular chaperone playing an important role in drug resistance and highly expressed in drug-resistant cancer forms, and thus represents the first small molecular anticancer lead with such a mode of action.