6-Methoxy-N-isopropyl-indol | 1968-15-6

• 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: 6-Methoxy-N-isopropyl-indol
• 英文别名: 6-Methoxy-1-propan-2-ylindole
• CAS: 1968-15-6
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: BVXFQAZQZVQCSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  6-Methoxy-N-isopropyl-indol 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 19.17h， 生成 2-(1-isopropyl-6-methoxy-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：

  2-碘代丙烷 、 6-甲氧基吲哚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以36%的产率得到6-Methoxy-N-isopropyl-indol
  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

文献信息

• Rh(<scp>iii</scp>)-Catalyzed regioselective C4 alkylation of indoles with allylic alcohols: direct access to β-indolyl ketones
  作者：Changduo Pan、Gao Huang、Yujia Shan、Yiting Li、Jin-Tao Yu

  DOI：10.1039/d0ob00396d

  日期：——

  A Rh(iii)-catalyzed and weak coordination carbonyl guided direct C4 alkylation of indoles with allylic alcohols was developed with excellent regioselectivity. This reaction was conducted under mild conditions, leading to a variety of β-indolyl ketones with good functional group tolerance in moderate to good yields.

  发展了Rh（iii）催化和弱配位羰基引导的吲哚与烯丙基醇的直接C4烷基化，具有出色的区域选择性。该反应在温和的条件下进行，从而以中等至良好的产率产生了各种具有良好的官能团耐受性的β-吲哚基酮。
• ACRYLANILIDE DERIVATIVE, PREPARATION METHOD, AND APPLICATIONS THEREOF IN PHARMACY
  申请人：Ancureall Pharmaceutical (Shanghai) Co., Ltd.

  公开号：US20190015413A1

  公开（公告）日：2019-01-17

  Disclosed in the present invention are an acrylanilide compound represented by general formula (I) and a pharmaceutically acceptable salt thereof. The acrylanilide compound and the pharmaceutically acceptable salt thereof are used for treating clinical diseases by mainly acting on EGFR family casein kinases.