2-amino-4-methoxy-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine | 115479-41-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 2-amino-4-methoxy-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• 英文别名: [(3aR,4R,6R,6aR)-4-(2-amino-4-methoxypyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 115479-41-9
• 化学式: C₁₅H₂₀N₄O₅
• 分子量: 336.348
• InChiKey: RKVVEWGKSPLMJY-VWMGYNLJSA-N

物化性质

• 沸点：
  603.3±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  113.88
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-amino-4-methoxy-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 在 N-碘代丁二酰亚胺 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 2,2-Dimethyl-propionic acid (3aR,4R,6R,6aR)-6-[2-(2,2-dimethyl-propionylamino)-5-iodo-4-methoxy-pyrrolo[2,3-d]pyrimidin-7-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  Synthesis of ribofuranosyl glycosides of echiguanines A and B, inhibitors of phosphatidylinositol 4-kinase

  摘要：

  The synthesis of ribofuranosyl glycosides of echiguanines A and B, PI 4-kinase inhibitors, was achieved from 2-amino-4-chloropyrrolo[2,3-d]pyrimidine and 2,3-O-isopropylidene-5-O-(t-butyl) dimethylsilyl-alpha-D-ribofuranosyl chloride. The ribofuranosyl echiguanine A weakly inhibited PI 4-kinase. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00459-3
• 作为产物：
  描述：

  7-{5'-O-[(1,1-dimethylethyl)dimethylsilyl]-2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl}-4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-2-amine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以701 g的产率得到2-amino-4-methoxy-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and structure-activity relationship of ribofuranosyl echiguanine analogs as inhibitors of phosphatidylinositol 4-kinase

  摘要：

  N-Substituted-2-amino-4(3H)-7H-oxopyrrolo[2,3-d]pyrimidine-5-carboxamides and their ribofuranosyl and 2',3'-dideoxyribofuranosyl derivatives were prepared as membrane permeable echiguanine analogs and tested for their ability to inhibit phosphatidylinositol (PI) 4-kinase. Compounds 5 and 6 were found to inhibit the enzyme approximately at the same level as echiguanines A and B. It is noteworthy that ribofuranosides 18, 19, and 20 and dideoxyribofuranoside 29 effectively inhibited PI 4-kinase. Thus, the terminal amide and related structures may be preferable for inhibition of the enzyme in echiguanine analogs with or without ribofuranoside. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00143-4

文献信息

• A facile synthesis of tubercidin and related 7-deazapurine nucleosides the stereospecific sodium salt glycosylation procedure
  作者：Kandasamy Ramasamy、Nobutaka Imamura、Roland K. Robins、Ganapathi R. Revankar

  DOI：10.1016/s0040-4039(00)95603-x

  日期：——

  A facile high-yield synthesis of 7-deazaadenosine (tubercidin, ), 7-deazaguanosine (), 2′-deoxy-7-deaza-6-thioguanosine () and 2′-deoxy-7-deazaguanosine () by the regioselective and stereospecific sodium salt glycosylation procedure is described.

  通过区域选择性和选择性合成简便的高产7-脱氮腺苷（胡椒丁），7-脱氮鸟苷（），2'-脱氧7-脱氮6-硫鸟苷（）和2'-脱氧7-脱氮鸟苷（）。描述了立体特异性钠盐糖基化的方法。
• RAMASAMY, KANDASAMY;IMAMURA, NOBUTAKA;ROBINS, ROLAND K.;REVANKAR, GANAPAT+, TETRAHEDRON LETT., 28,(1987) N 43, 5107-5110
  作者：RAMASAMY, KANDASAMY、IMAMURA, NOBUTAKA、ROBINS, ROLAND K.、REVANKAR, GANAPAT+

  DOI：——

  日期：——