2-iodo-3-((3,4,5-trimethoxyphenyl)thio)-1H-indole | 1416576-75-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-iodo-3-((3,4,5-trimethoxyphenyl)thio)-1H-indole
• 英文别名: 2-iodo-3-(3,4,5-trimethoxyphenyl)sulfanyl-1H-indole
• CAS: 1416576-75-4
• 化学式: C₁₇H₁₆INO₃S
• 分子量: 441.289
• InChiKey: BPGJHWUNVJWHRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(triethylstannyl)-1H-indole-1-carboxylic acid 、 2-iodo-3-((3,4,5-trimethoxyphenyl)thio)-1H-indole 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以20%的产率得到2-(1H-indol-2-yl)-3-(3,4,5-trimethoxyphenyl)sulfanyl-1H-indole
  参考文献：
  名称：

  Toward Highly Potent Cancer Agents by Modulating the C-2 Group of the Arylthioindole Class of Tubulin Polymerization Inhibitors

  摘要：

  New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized S. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCl/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.

  DOI：

  10.1021/jm3013097
• 作为产物：
  描述：

  2-碘-1H-吲哚 、 bis(3,4,5-trimethoxyphenyl)disulfide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.25h， 以93%的产率得到2-iodo-3-((3,4,5-trimethoxyphenyl)thio)-1H-indole
  参考文献：
  名称：

  Toward Highly Potent Cancer Agents by Modulating the C-2 Group of the Arylthioindole Class of Tubulin Polymerization Inhibitors

  摘要：

  New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized S. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCl/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.

  DOI：

  10.1021/jm3013097