[2-[1-(benzenesulfonyl)pyrrol-3-yl]-1H-indol-3-yl]-(3,4,5-trimethoxyphenyl)methanol | 1416576-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-[1-(benzenesulfonyl)pyrrol-3-yl]-1H-indol-3-yl]-(3,4,5-trimethoxyphenyl)methanol
• CAS: 1416576-18-5
• 化学式: C₂₈H₂₆N₂O₆S
• 分子量: 518.59
• InChiKey: VGWNFUURVFEVQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-[1-(benzenesulfonyl)pyrrol-3-yl]-1H-indol-3-yl]-(3,4,5-trimethoxyphenyl)methanol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以98%的产率得到[2-(1H-pyrrol-3-yl)-1H-indol-3-yl]-(3,4,5-trimethoxyphenyl)methanol
  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-(1-(phenylsulfonyl)-1H-pyrrol-3-yl)-1H-indole 在 aluminum (III) chloride 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 25.0~110.0 ℃ 、1.72 MPa 条件下， 反应 2.05h， 生成 [2-[1-(benzenesulfonyl)pyrrol-3-yl]-1H-indol-3-yl]-(3,4,5-trimethoxyphenyl)methanol
  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