9-[5',6'-dideoxy-2',3'-O-isopropylidene-6'-phthalimido-β-L-ribo-hex-5'(E)-enofuranosyl] adenosine | 770728-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 9-[5',6'-dideoxy-2',3'-O-isopropylidene-6'-phthalimido-β-L-ribo-hex-5'(E)-enofuranosyl] adenosine
• CAS: 770728-25-1
• 化学式: C₂₃H₂₂N₆O₅
• 分子量: 462.465
• InChiKey: WXEJKWUUYOOHLV-PUYSDXPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  134.69
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  9-[5',6'-dideoxy-2',3'-O-isopropylidene-6'-phthalimido-β-L-ribo-hex-5'(E)-enofuranosyl] adenosine 在 甲胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以93%的产率得到9-[5',6'-dideoxy-2',3'-O-isopropylidene-6'-aminomethyl-β-L-ribo-hex-5'(E)-enofuranosyl] adenosine
  参考文献：
  名称：

  Synthesis and biological activities of 5′-ethylenic and acetylenic modified l-nucleosides and isonucleosides

  摘要：

  Two series of 6'-halovinyl-adenosine stereoisomers including 5'-ethylenic and acetylenic substituted L-adenosine, 5'-ethylenic and acetylenic substituted isonucleosides were synthesized. In the L-nucleoside series, compounds 6b, 8b, 10b and 13b showed modest inhibition of SAH hydrolase (21, 44, 50 and 26% respectively) at 100 muM. The L-isomers of 5'-ethylenic and acetylenic modified isonucleoside 23, 24 exhibited no activity for the inhibition of SAH hydrolase, however, the D-isomers 30 and 31 showed some activities in the same test (35 and 21%). It indicated clearly the strict stereochemical requirement for the substrate of SAH hydrolase. Compounds 6b, 8b, 8c, 11b exhibited modest to good inhibition effects on the growth of HeLa cells or Bel-7420 cells at 1 muM (64, 44, 53 and 82% respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.131
• 作为产物：
  描述：

  2',3'-isopropylideneadenosine 在 二氯乙酸 、 二异丁基氢化铝 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 9-[5',6'-dideoxy-2',3'-O-isopropylidene-6'-phthalimido-β-L-ribo-hex-5'(E)-enofuranosyl] adenosine
  参考文献：
  名称：

  Synthesis and biological activities of 5′-ethylenic and acetylenic modified l-nucleosides and isonucleosides

  摘要：

  Two series of 6'-halovinyl-adenosine stereoisomers including 5'-ethylenic and acetylenic substituted L-adenosine, 5'-ethylenic and acetylenic substituted isonucleosides were synthesized. In the L-nucleoside series, compounds 6b, 8b, 10b and 13b showed modest inhibition of SAH hydrolase (21, 44, 50 and 26% respectively) at 100 muM. The L-isomers of 5'-ethylenic and acetylenic modified isonucleoside 23, 24 exhibited no activity for the inhibition of SAH hydrolase, however, the D-isomers 30 and 31 showed some activities in the same test (35 and 21%). It indicated clearly the strict stereochemical requirement for the substrate of SAH hydrolase. Compounds 6b, 8b, 8c, 11b exhibited modest to good inhibition effects on the growth of HeLa cells or Bel-7420 cells at 1 muM (64, 44, 53 and 82% respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.131