(2-(pyridin-2-yl)-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone | 1416576-48-1

• 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: (2-(pyridin-2-yl)-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone
• 英文别名: (2-pyridin-2-yl-1H-indol-3-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1416576-48-1
• 化学式: C₂₃H₂₀N₂O₄
• 分子量: 388.423
• InChiKey: IAAJNRDUDUIILQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-acetylpyridine phenylhydrazone 在 甲基溴化镁 、 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2-(pyridin-2-yl)-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone
  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

文献信息

• Cerium(III)-catalyzed C3-acylation of indoles with nitroolefins
  作者：Cheng-Tao Feng、Hui-Zhi Zhu、Zhong Li、Zaigang Luo、Song-Song Wu、Shi-Tang Ma

  DOI：10.1016/j.tetlet.2016.01.029

  日期：2016.2

  A novel and efficient cerium(III)-catalyzed C3-selective acylation of N–H indoles using nitroolefins as acylating reagents was first developed. It was found that the use of CeCl3 as a catalyst achieves an unexpected and highly efficient C–C bond cleavage.

  首次开发了一种新型高效的铈（III）催化的硝基苯吲哚的C3选择性C3选择性酰化反应，该反应使用硝基烯烃作为酰化试剂。发现使用CeCl 3作为催化剂可实现意想不到且高效的C–C键裂解。