(S)-4-((2-(1H-indol-4-yl)ethyl)(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy tetrahydrofuran-2-yl)methyl)amino)-2-aminobutanoic acid | 1373432-66-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (S)-4-((2-(1H-indol-4-yl)ethyl)(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy tetrahydrofuran-2-yl)methyl)amino)-2-aminobutanoic acid
• 英文别名: (2S)-2-amino-4-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-[2-(1H-indol-4-yl)ethyl]amino]butanoic acid
• CAS: 1373432-66-6
• 化学式: C₂₄H₃₀N₈O₅
• 分子量: 510.553
• InChiKey: TYTSCDAWXBZJKA-WUASKDLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(1H-吲哚)-4-乙酸 在 三乙基硅烷 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 三乙酰氧基硼氢化钠 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 苯甲醚 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 15.0h， 生成 (S)-4-((2-(1H-indol-4-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

文献信息

• Development of rationally designed DNA N6 adenine methyltransferase inhibitors
  作者：Gerard Hobley、Jennifer C. McKelvie、Jenny E. Harmer、Jason Howe、Petra C.F. Oyston、Peter L. Roach

  DOI：10.1016/j.bmcl.2012.03.072

  日期：2012.5

  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.