S-ethyl 2-(benzo[b]thiophen-3-yl)ethanethioate | 1373432-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: S-ethyl 2-(benzo[b]thiophen-3-yl)ethanethioate
• 英文别名: S-ethyl 2-(1-benzothiophen-3-yl)ethanethioate
• CAS: 1373432-55-3
• 化学式: C₁₂H₁₂OS₂
• 分子量: 236.359
• InChiKey: VRQDEFYGRTYJKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-ethyl 2-(benzo[b]thiophen-3-yl)ethanethioate 在 三乙基硅烷 、 palladium 10% on activated carbon 、 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 水 、 苯甲醚 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 15.0h， 生成 (S)-2-amino-4-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(2-(benzo[b]thiophen-3-yl)ethyl)amino)butanoic 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：

  苯并[b]噻吩-3-乙酸 、 乙硫醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到S-ethyl 2-(benzo[b]thiophen-3-yl)ethanethioate
  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.