ethyl 5-((phenylamino)methyl)benzo[b]thiophene-2-carboxylate | 947513-36-2

• 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: ethyl 5-((phenylamino)methyl)benzo[b]thiophene-2-carboxylate
• CAS: 947513-36-2
• 化学式: C₁₈H₁₇NO₂S
• 分子量: 311.404
• InChiKey: NGGFMNFFRYLVOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-((phenylamino)methyl)benzo[b]thiophene-2-carboxylate 在 羟胺 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 5-phenylaminomethyl-benzo[b]thiophene-2-carboxylic acid hydroxyamide
  参考文献：
  名称：

  Benzo[b]thiophene-based histone deacetylase inhibitors

  摘要：

  Benzo[b]thienyl hydroxamic acids, a novel class of historic deacetylase (HDAC) inhibitors, were identified via a targeted screen of small molecule hydroxamic acids. Various substitutions were explored in the C5- and C6-positions of the benzo[b]thiophene core to characterize SAR and develop optimal inhibitors. It was determined that substitution at the C6-position of the benzo[b]thiophene core with a three-atom spacer yielded optimal HDAC I inhibition and anti-proliferative activity in murine erythroleukemia (SC-9) cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.091
• 作为产物：
  描述：

  5-氨基-1-苯并噻吩-2-羧酸乙酯 在 盐酸 、 异丙基溴化镁 、 三乙酰氧基硼氢化钠 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 生成 ethyl 5-((phenylamino)methyl)benzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Benzo[b]thiophene-based histone deacetylase inhibitors

  摘要：

  Benzo[b]thienyl hydroxamic acids, a novel class of historic deacetylase (HDAC) inhibitors, were identified via a targeted screen of small molecule hydroxamic acids. Various substitutions were explored in the C5- and C6-positions of the benzo[b]thiophene core to characterize SAR and develop optimal inhibitors. It was determined that substitution at the C6-position of the benzo[b]thiophene core with a three-atom spacer yielded optimal HDAC I inhibition and anti-proliferative activity in murine erythroleukemia (SC-9) cells. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.091