7-butoxy-1H-indole-3-carbaldehyde | 910624-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-butoxy-1H-indole-3-carbaldehyde
• CAS: 910624-63-4
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: BHDXTYBEFFOJQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  399.8±22.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-butoxy-1H-indole-3-carbaldehyde 在 哌啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.0h， 生成 5-[(7-butoxy-1H-indol-3-yl)methyl]-3-methylimidazolidine-2,4-dione
  参考文献：
  名称：

  Structure–activity relationship study of novel necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.077
• 作为产物：
  描述：

  7-苄氧基吲哚 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 20.0h， 生成 7-butoxy-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Structure–activity relationship study of novel necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.077

文献信息

• ANTICANCER AGENT
  申请人：Nagano Tetsuo

  公开号：US20130102776A1

  公开（公告）日：2013-04-25

  An anticancer agent comprising a compound represented by the formula (I) [R 1 represents hydrogen atom, hydroxyl group, a C 1-6 alkoxy group and the like; R 2 and R 3 represents hydrogen atom, a halogen atom, a C 1-6 alkyl group and the like; R 4 represents hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkylsulfonyl group and the like; R 5 represents hydrogen atom or a substituent; represents a single bond or a double bond; R 6 and R 7 represents hydrogen atom, a C 1-6 alkyl group and the like; R 8 represents hydrogen atom, a C 1-6 alkyl group and the like; A represents —O—, —S—, or —CH 2 —; D represents —C═ or —N═; X represents methylene group, —O—, or —CO—; Q represents —N═ or —C(R 8 )═; and Y represents a heterocyclic group or amino group], which shows a superior inhibitory activity against pim-1 kinase.

  一种抗癌剂，包括由式(I)所表示的化合物[其中R1代表氢原子、羟基、C1-6烷氧基等；R2和R3代表氢原子、卤原子、C1-6烷基等；R4代表氢原子、C1-6烷基、C1-6烷基磺酰基等；R5代表氢原子或取代基；代表单键或双键；R6和R7代表氢原子、C1-6烷基等；R8代表氢原子、C1-6烷基等；A代表—O—、—S—或—CH2—；D代表—C═或—N═；X代表亚甲基、—O—或—CO—；Q代表—N═或—C(R8)═；Y代表杂环基或氨基]，该化合物对pim-1激酶表现出优异的抑制活性。
• US9156827B2
  申请人：——

  公开号：US9156827B2

  公开（公告）日：2015-10-13
• Structure–activity relationship study of novel necroptosis inhibitors
  作者：Xin Teng、Alexei Degterev、Prakash Jagtap、Xuechao Xing、Sungwoon Choi、Régine Denu、Junying Yuan、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2005.07.077

  日期：2005.11

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.