5-chloro-1-(2-methoxyethyl)-1H-indole | 1313042-80-6

• 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: 5-chloro-1-(2-methoxyethyl)-1H-indole
• 英文别名: 4-chloro-1-(2-methoxy-ethyl)-1H-indole；4-chloro-1-(2-methoxyethyl)indole
• CAS: 1313042-80-6
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: VTCLVUWCFLMCFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-1-(2-methoxyethyl)-1H-indole 在 aluminum (III) chloride 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 2-(5-chloro-1-(2-methoxyethyl)-1H-indol-3-yl)-N-(6-methoxypyridin-3-yl)-2-oxoacetamide
  参考文献：
  名称：

  An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer

  摘要：

  A number of indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors, although none has yet been successfully developed clinically. We report here a new series of related compounds, modified according to a strategy of reducing aromatic ring count and introducing a greater degree of saturation, which retain potent tubulin polymerization activity but with a distinct SAR from previously documented libraries. A subset of active compounds from the reported series is shown to interact with tubulin at the colchicine binding site, disrupt the cellular microtubule network, and exert a cytotoxic effect against multiple cancer cell lines. Two compounds demonstrated significant tumor growth inhibition in a mouse xenograft model of head and neck cancer, a type of the disease which often proves resistant to chemotherapy, supporting further development of the current series as potential new therapeutics.

  DOI：

  10.1021/acs.jmedchem.5b01312
• 作为产物：
  描述：

  4-氯吲哚 、 2-溴乙基甲基醚 在 sodium iodide sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.17h， 以100%的产率得到5-chloro-1-(2-methoxyethyl)-1H-indole
  参考文献：
  名称：

  [EN] INDOLYL-PIPERIDINYL BENZYLAMINES AS BETA-TRYPTASE INHIBITORS
  [FR] INDOLYL-PIPÉRIDINYL BENZYLAMINES INHIBITRICES DE LA BÊTA-TRYPTASE

  摘要：

  本发明公开并要求一系列取代的吲哚基-哌啶基苄胺化合物，其公式为（I），其中R1、R2和R3如本文所述。更具体地说，本发明的化合物是β-tryptase的抑制剂，因此可用作药物制剂。此外，本发明还公开了取代的吲哚基-哌啶基苄胺的制备方法。在其中一个实施例中，提供了公式（I）的化合物，其中R3是（II）。

  公开号：

  WO2011079102A1

文献信息

• INDOLYL-PIPERIDINYL BENZYLAMINES AS BETA-TRYPTASE INHIBITORS
  申请人：CHOI-SLEDESKI Yong Mi

  公开号：US20120245161A1

  公开（公告）日：2012-09-27

  The present invention discloses and claims a series of substituted indolyl-piperidinyl benzylamines of the formula wherein R1, R2, R4 and R5 are as described herein. More specifically, the compounds of this invention are inhibitors of β-tryptase and are, therefore, useful as pharmaceutical agents. Additionally, this invention also discloses methods of preparation of substituted indolyl-piperidinyl benzylamines.

  本发明披露和声称一系列被取代的indolyl-piperidinyl benzylamines，其化学式为其中R1、R2、R4和R5如本文所述。更具体地说，本发明的化合物是β-tryptase的抑制剂，因此可用作制药剂。此外，本发明还披露了取代的indolyl-piperidinyl benzylamines的制备方法。