(2R,3R,4S)-4-(6-aminopurin-9-yl)-2-(dimethoxymethyl)oxolan-3-ol | 136025-01-9

• 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: (2R,3R,4S)-4-(6-aminopurin-9-yl)-2-(dimethoxymethyl)oxolan-3-ol
• CAS: 136025-01-9
• 化学式: C₁₂H₁₇N₅O₄
• 分子量: 295.298
• InChiKey: XYDALHCGTHICBK-NBEYISGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-4-(6-aminopurin-9-yl)-2-(dimethoxymethyl)oxolan-3-ol 在 溶剂黄146 、 sodium nitrite 作用下， 反应 48.0h， 以60%的产率得到3'-(S)-(hypoxanthin-9-yl)-4'-(R)-hydroxy-5'-(S)-dimethoxymethyl-tetrahydrofuran
  参考文献：
  名称：

  Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines

  摘要：

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00048-x
• 作为产物：
  描述：

  2,5-Anhydro-D-xylose dimethyl acetal 3-(4-methylbenzenesulfonate) 在 18-冠醚-6 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 (2R,3R,4S)-4-(6-aminopurin-9-yl)-2-(dimethoxymethyl)oxolan-3-ol
  参考文献：
  名称：

  Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines

  摘要：

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00048-x

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.
• Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines
  作者：Hong-Wu Yu、Liang-Ren Zhang、Ji-Chang Zhou、Ling-Tai Ma、Li-He Zhang

  DOI：10.1016/0968-0896(96)00048-x

  日期：1996.4

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd