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 | 185425-34-7

• 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: 2,2-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
• CAS: 185425-34-7
• 化学式: C₂₅H₃₅IN₄O₇
• 分子量: 630.48
• InChiKey: FOYHDQDLLATVOX-NVQRDWNXSA-N

物化性质

• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  123.03
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  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 在 palladium on activated charcoal ammonium hydroxide 、 bis(triphenylphosphine)palladium(II)-chloride 、 碘代三甲硅烷 、 氨 、 氢气 、 三氟乙酸 、 三甲氧基磷 作用下， 以 吡啶 、 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 52.0h， 生成 2-Amino-7-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (2-cyano-ethyl)-amide
  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
• 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 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 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

• Synthesis of ribofuranosyl glycosides of echiguanines A and B, inhibitors of phosphatidylinositol 4-kinase
  作者：Kasumi Sanpei、Yoshio Saito、Masaya Imoto、Kazuo Umezawa、Kuniki Kato

  DOI：10.1016/0960-894x(96)00459-3

  日期：1996.11

  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