5-氯-3-[(3,5-二甲氧基苯基)硫代]-1H-吲哚-2-羧酸 | 1026883-23-7

• 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
• 中文名称: 5-氯-3-[(3,5-二甲氧基苯基)硫代]-1H-吲哚-2-羧酸
• 英文名称: 5-chloro-3-[(3,5-dimethoxyphenyl)thio]-1H-indole-2-carboxylic acid
• 英文别名: 5-chloro-3-(3,5-dimethoxyphenyl)sulfanyl-1H-indole-2-carboxylic acid
• CAS: 1026883-23-7
• 化学式: C₁₇H₁₄ClNO₄S
• 分子量: 363.821
• InChiKey: AWVYLTMPQBJCJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氯-3-[(3,5-二甲氧基苯基)硫代]-1H-吲哚-2-羧酸 、 三甲基硅烷化重氮甲烷 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl 5-chloro-3-[(3,5-dimethoxyphenyl)thio]-1H-indole-2-carboxylate
  参考文献：
  名称：

  New Arylthioindoles:  Potent Inhibitors of Tubulin Polymerization. 2. Structure−Activity Relationships and Molecular Modeling Studies

  摘要：

  Arylthioindoles (ATIs) that possess a 3-methoxyphenylthio or a 3,5-dimethoxyphenylthio moiety at position 2 of the indole ring were effective tubulin assembly inhibitors, but weak inhibitors of MCF-7 cell growth. ATIs bearing a 3-(3,4,5-trimethoxyphenyl)thio moiety were potent tubulin polymerization inhibitors, with IC(50)s in the 2.0 (35) to 4.5 (37) mu M range. They also inhibited MCF-7 cell growth at nanomolar concentrations. The 3,4,5-trimethoxy substituted ATIs showed potencies comparable to those of the reference compounds colchicine and combretastatin A-4 in both tubulin assembly and cell growth inhibition assays. Dynamics simulation studies correlate well with the observed experimental data. Furthermore, from careful analysis of the biological and in silico data, we can now hypothesize a basic pharmacophore for this class of compounds.

  DOI：

  10.1021/jm050809s
• 作为产物：
  描述：

  3,5-二甲氧基苯胺 在 盐酸 、 碘 、 sodium hydride 、 sodium nitrite 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 5-氯-3-[(3,5-二甲氧基苯基)硫代]-1H-吲哚-2-羧酸
  参考文献：
  名称：

  New Arylthioindoles:  Potent Inhibitors of Tubulin Polymerization. 2. Structure−Activity Relationships and Molecular Modeling Studies

  摘要：

  Arylthioindoles (ATIs) that possess a 3-methoxyphenylthio or a 3,5-dimethoxyphenylthio moiety at position 2 of the indole ring were effective tubulin assembly inhibitors, but weak inhibitors of MCF-7 cell growth. ATIs bearing a 3-(3,4,5-trimethoxyphenyl)thio moiety were potent tubulin polymerization inhibitors, with IC(50)s in the 2.0 (35) to 4.5 (37) mu M range. They also inhibited MCF-7 cell growth at nanomolar concentrations. The 3,4,5-trimethoxy substituted ATIs showed potencies comparable to those of the reference compounds colchicine and combretastatin A-4 in both tubulin assembly and cell growth inhibition assays. Dynamics simulation studies correlate well with the observed experimental data. Furthermore, from careful analysis of the biological and in silico data, we can now hypothesize a basic pharmacophore for this class of compounds.

  DOI：

  10.1021/jm050809s

文献信息

• New Arylthioindoles:  Potent Inhibitors of Tubulin Polymerization. 2. Structure−Activity Relationships and Molecular Modeling Studies
  作者：Gabriella De Martino、Michael C. Edler、Giuseppe La Regina、Antonio Coluccia、Maria Chiara Barbera、Denise Barrow、Robert I. Nicholson、Gabriela Chiosis、Andrea Brancale、Ernest Hamel、Marino Artico、Romano Silvestri

  DOI：10.1021/jm050809s

  日期：2006.2.1

  Arylthioindoles (ATIs) that possess a 3-methoxyphenylthio or a 3,5-dimethoxyphenylthio moiety at position 2 of the indole ring were effective tubulin assembly inhibitors, but weak inhibitors of MCF-7 cell growth. ATIs bearing a 3-(3,4,5-trimethoxyphenyl)thio moiety were potent tubulin polymerization inhibitors, with IC(50)s in the 2.0 (35) to 4.5 (37) mu M range. They also inhibited MCF-7 cell growth at nanomolar concentrations. The 3,4,5-trimethoxy substituted ATIs showed potencies comparable to those of the reference compounds colchicine and combretastatin A-4 in both tubulin assembly and cell growth inhibition assays. Dynamics simulation studies correlate well with the observed experimental data. Furthermore, from careful analysis of the biological and in silico data, we can now hypothesize a basic pharmacophore for this class of compounds.