3-(thiophen-3-yl-ethynyl)-1-(2,3,5-tri-hydroxy-β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylic acid amide | 1106736-29-1

• 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: 3-(thiophen-3-yl-ethynyl)-1-(2,3,5-tri-hydroxy-β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylic acid amide
• 英文别名: 3-(thiophen-3-yl-ethynyl)-1-(β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylic acid amide；2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-thiophen-3-ylethynyl)-1,2,4-triazole-3-carboxamide
• CAS: 1106736-29-1
• 化学式: C₁₄H₁₄N₄O₅S
• 分子量: 350.355
• InChiKey: FMWGKZCPDYLIQI-IDTAVKCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 3-(thiophen-3-ylethynyl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylate 在 甲醇 、 氨 作用下， 反应 48.0h， 以76%的产率得到3-(thiophen-3-yl-ethynyl)-1-(2,3,5-tri-hydroxy-β-D-ribofuranosyl)-1H-[1,2,4]triazole-5-carboxylic acid amide
  参考文献：
  名称：

  [EN] TRIAZOLE DERIVATIVES AS VIRAL REPLICATION INHIBITORS
  [FR] NOUVEAUX INHIBITEURS DE RÉPLICATION VIRALE

  摘要：

  公开号：

  WO2009015446A3

文献信息

• [EN] TRIAZOLE DERIVATIVES AS VIRAL REPLICATION INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE RÉPLICATION VIRALE
  申请人：UNIV LEUVEN KATH

  公开号：WO2009015446A3

  公开（公告）日：2009-03-19
• 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.