1-(thiophen-3-ylmethyl)-1H-indole | 605663-22-7

• 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
• 英文名称: 1-(thiophen-3-ylmethyl)-1H-indole
• 英文别名: 1-(Thiophen-3-ylmethyl)indole
• CAS: 605663-22-7
• 化学式: C₁₃H₁₁NS
• 分子量: 213.303
• InChiKey: OKTQSMCQWCHRCM-UHFFFAOYSA-N

物化性质

• 沸点：
  386.4±25.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-溴甲基噻吩 、 吲哚 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-(thiophen-3-ylmethyl)-1H-indole
  参考文献：
  名称：

  BPR0C305, an orally active microtubule-disrupting anticancer agent

  摘要：

  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.

  DOI：

  10.1097/cad.0000000000000014

文献信息

• Novel compounds and methods of use thereof
  申请人：——

  公开号：US20030181482A1

  公开（公告）日：2003-09-25

  This invention relates to novel heteroatom containing compounds and compositions thereof, and their use for the prevention and treatment of disease. The invention also provides for methods of making the compounds. The invention is based on the discovery that certain heteroatom containing compounds, 3-oxoacetamideindolyl compounds, have potent anticancer, cytotoxic, and anti-angiogenic activity.

  本发明涉及含有杂原子的新型化合物及其组合物，以及它们在预防和治疗疾病方面的用途。本发明还提供了制造这些化合物的方法。本发明的基础是发现某些含杂原子的化合物--3-氧代乙酰胺吲哚基化合物具有强效的抗癌、细胞毒性和抗血管生成活性。
• Novel Compounds And Methods Of Use Thereof
  申请人：Chen Chiung-Tong

  公开号：US20080242701A1

  公开（公告）日：2008-10-02

  This invention relates to treating cancer or an angiogenesis-related disease using a compound of formula 1: wherein R 1 , R 2 , R 3 , R 4 , and n are defined herein.
• US6903104B2
  申请人：——

  公开号：US6903104B2

  公开（公告）日：2005-06-07
• US7396838B2
  申请人：——

  公开号：US7396838B2

  公开（公告）日：2008-07-08
• US7662834B2
  申请人：——

  公开号：US7662834B2

  公开（公告）日：2010-02-16