(S)-tert-butyl-4-((2-(1H-indol-3-yl)ethyl)(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)amino)-2-((tert-butoxycarbonyl) amino)butanoate | 1373432-58-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (S)-tert-butyl-4-((2-(1H-indol-3-yl)ethyl)(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)amino)-2-((tert-butoxycarbonyl) amino)butanoate
• CAS: 1373432-58-6
• 化学式: C₃₆H₅₀N₈O₇
• 分子量: 706.842
• InChiKey: JFZOCGMKDANIEA-CYZHESPZSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  51.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  180.97
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl-4-((2-(1H-indol-3-yl)ethyl)(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)amino)-2-((tert-butoxycarbonyl) amino)butanoate 在 三氟乙酸 作用下， 以 水 、 苯甲醚 为溶剂， 反应 3.0h， 以65%的产率得到(S)-4-((2-(1H-indol-3-yl)ethyl)(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)methyl)amino)-2-aminobutanoic acid
  参考文献：
  名称：

  Development of rationally designed DNA N6 adenine methyltransferase inhibitors

  摘要：

  A series of bisubstrate inhibitors for DNA N6 adenine methyltransferase (Dam) have been synthesized by linking an amine analogue of S-adenosylmethionine to an aryl moiety designed to probe the binding pocket of the DNA adenine base. An initial structure-activity relationship study has identified substituents that increase inhibitor potency to the similar to 10 mu M range and improve selectivity against the human cytosine methyltransferase Dnmt1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.072
• 作为产物：
  描述：

  5-氨基-5-脱氧-2,3-O-(1-甲基亚乙基)-腺苷酸 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 15.0h， 生成 (S)-tert-butyl-4-((2-(1H-indol-3-yl)ethyl)(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)amino)-2-((tert-butoxycarbonyl) amino)butanoate
  参考文献：
  名称：

  Development of rationally designed DNA N6 adenine methyltransferase inhibitors

  摘要：

  A series of bisubstrate inhibitors for DNA N6 adenine methyltransferase (Dam) have been synthesized by linking an amine analogue of S-adenosylmethionine to an aryl moiety designed to probe the binding pocket of the DNA adenine base. An initial structure-activity relationship study has identified substituents that increase inhibitor potency to the similar to 10 mu M range and improve selectivity against the human cytosine methyltransferase Dnmt1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.072