4-[(2R,3S,4R,5R)-5-(6-amino-8-benzylamino-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-ylmethoxymethyl]benzonitrile | 1134156-34-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 4-[(2R,3S,4R,5R)-5-(6-amino-8-benzylamino-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-ylmethoxymethyl]benzonitrile
• 英文别名: Adenosine-derived inhibitor, 13；4-[[(2R,3S,4R,5R)-5-[6-amino-8-(benzylamino)purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxymethyl]benzonitrile
• CAS: 1134156-34-5
• 化学式: C₂₅H₂₅N₇O₄
• 分子量: 487.518
• InChiKey: VVUSRKLKGUETQD-UMCMBGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  164
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-[[(3aR,4R,6R,6aR)-4-[6-amino-8-(benzylamino)purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxymethyl]benzonitrile 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以59%的产率得到4-[(2R,3S,4R,5R)-5-(6-amino-8-benzylamino-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-ylmethoxymethyl]benzonitrile
  参考文献：
  名称：

  Novel Adenosine-Derived Inhibitors of 70 kDa Heat Shock Protein, Discovered Through Structure-Based Design

  摘要：

  The design and synthesis of novel adenosine-derived inhibitors of HSP70, guided by modeling and X-ray crystallographic structures of these compounds in complex with HSC70/BAG-1, is described. Examples exhibited submicromolar affinity for HSP70, were highly selective over HSP90, and some displayed potency against HCT116 cells. Exposure of compound 12 to HCT116 cells caused significant reduction in cellular levels of Raf-1 and Her2 at concentrations similar to that which caused cell growth arrest.

  DOI：

  10.1021/jm801627a