N₁-(6-quinolyl)-2-oxo-2-[1-(3-thienylmethyl)-1H-indol-3-yl]acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N₁-(6-quinolyl)-2-oxo-2-[1-(3-thienylmethyl)-1H-indol-3-yl]acetamide
• 英文别名: 2-oxo-N-quinolin-6-yl-2-[1-(thiophen-3-ylmethyl)indol-3-yl]acetamide
• 化学式: C₂₄H₁₇N₃O₂S
• 分子量: 411.484
• InChiKey: VXZSGTDWGQPRCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(thiophen-3-ylmethyl)-1H-indole 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 N₁-(6-quinolyl)-2-oxo-2-[1-(3-thienylmethyl)-1H-indol-3-yl]acetamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N-Heterocyclic Indolyl Glyoxylamides as Orally Active Anticancer Agents

  摘要：

  A series of N-heterocyclic indolyl glyoxylamides were synthesized and evaluated for in vitro and in vivo anticancer activities. They exhibited a broad spectrum of anticancer activity not only in murine leukemic cancer cells but also in human gastric, breast, and uterus cancer cells as well as their multidrug resistant sublines with a wide range of IC50 values. They also induced apoptosis and caused DNA fragmentation in human gastric cancer cells. Among the compounds studied, 7 showed the most potent activity of growth inhibition (IC50 = 17-1711 nM) in several human cancer cells. Given orally, compounds 7 and 13 dose-dependently prolonged the survival of animals inoculated with P388 leukemic cancer cells. N-Heterocyclic indolyl glyoxylamides may be useful as orally active chemotherapeutic agents against cancer and refractory cancerous diseases of multidrug resistance phenotype.

  DOI：

  10.1021/jm020471r

文献信息

• BPR0C305, an orally active microtubule-disrupting anticancer agent
  作者：Wen-Tai Li、Teng-Kuang Yeh、Jen-Shin Song、Yung-Ning Yang、Tung-Wei Chen、Chi-Hung Lin、Ching-Ping Chen、Chien-Chang Shen、Chih-Chien Hsieh、Heng-Liang Lin、Yu-Sheng Chao、Chiung-Tong Chen

  DOI：10.1097/cad.0000000000000014

  日期：2013.11

  BPR0C305 is a novel N-substituted indolyl glyoxylamide previously reported with in-vitro cytotoxic activity against a panel of human cancer cells including P-gp-expressing multiple drug-resistant cell sublines. The present study further examined the underlying molecular mechanism of anticancer action and evaluated the in-vivo antitumor activities of BPR0C305. BPR0C305 is a novel synthetic small indole derivative that demonstrates in-vitro activities against human cancer cell growth by inhibiting tubulin polymerization, disrupting cellular microtubule assembly, and causing cell cycle arrest at the G2/M phase. It is also orally active against leukemia and solid tumor growths in mouse models. Findings of these pharmacological and pharmacokinetic studies suggest that BPR0C305 is a promising lead compound for further preclinical developments.