6-N-benzoyl-9-[5'-deoxy-5'-iodo-2',3'-O-isopropylidene-β-L-ribo-hex-5'(E)-enofuranosyl] adenosine | 770728-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-N-benzoyl-9-[5'-deoxy-5'-iodo-2',3'-O-isopropylidene-β-L-ribo-hex-5'(E)-enofuranosyl] adenosine
• 英文别名: N-[9-[(3aS,4S,6R,6aR)-6-(iodomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-yl]benzamide
• CAS: 770728-22-8
• 化学式: C₂₀H₂₀IN₅O₄
• 分子量: 521.314
• InChiKey: SCFMQQDZPFBOLD-XPVILTJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  100.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-9-[5'-deoxy-5'-iodo-2',3'-O-isopropylidene-β-L-ribo-hex-5'(E)-enofuranosyl] adenosine 在 氨 作用下， 以 甲醇 为溶剂， 生成 9-((3aS,4S,6R,6aR)-6-Iodomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-ylamine
  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：

  9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-N-benzoyladenine 在 吡啶 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 丙酮 为溶剂， 反应 21.2h， 生成 6-N-benzoyl-9-[5'-deoxy-5'-iodo-2',3'-O-isopropylidene-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

文献信息

• Synthesis and biological activities of 5′-ethylenic and acetylenic modified l-nucleosides and isonucleosides
  作者：Jun-Feng Wang、Xiao-Da Yang、Liang-Ren Zhang、Zhen-Jun Yang、Li-He Zhang

  DOI：10.1016/j.tet.2004.06.131

  日期：2004.9

  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.