5'-nonanoyl-O-adenosine

• 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: 5'-nonanoyl-O-adenosine
• 英文别名: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl nonanoate
• 化学式: C₁₉H₂₉N₅O₅
• 分子量: 407.47
• InChiKey: HTBGORAUJWANQC-BGIGGGFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 5'-nonanoyl-O-adenosine
  参考文献：
  名称：

  Estradiol−Adenosine Hybrid Compounds Designed to Inhibit Type 1 17β-Hydroxysteroid Dehydrogenase

  摘要：

  The steroidogenic enzyme type 1 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) is involved in the synthesis of estradiol (E-2), a hormone well-known to stimulate the growth of estrogen-sensitive tumors. To obtain compounds able to control E-2 formation, two moieties were linked with a methylene side chain: an adenosine moiety for interacting with the cofactor-binding site and an E-2 moiety for interacting with the substrate-binding site. When tested as inhibitors of type 1 17 beta-HSD, the hybrid compounds inhibited the reductive activity (E-1 into E-2) with IC50 values ranging from 52 to 1000 nM. The optimal side-chain length was determined to be eight methylene groups for a 16 beta-orientation. The presence of two components (E-2 and adenosine) is essential for good inhibition, since 16 beta-nonyl-E-2 and 5-nonanoyl-O-adenosine, two compounds having only one of the components, did not inhibit the enzyme. Moreover, the 3D-structure analysis of EM-1745 complexed with type 1 17 beta-HSD showed key interactions with both substrate- and cofactor-binding sites.

  DOI：

  10.1021/jm058235e