1-(4-chloro-2-methoxybenzyl)-1H-indole | 1192485-79-2

• 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-(4-chloro-2-methoxybenzyl)-1H-indole
• CAS: 1192485-79-2
• 化学式: C₁₆H₁₄ClNO
• 分子量: 271.746
• InChiKey: BAQGUQQJDNPLHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  14.16
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  草酰氯 、 1-(4-chloro-2-methoxybenzyl)-1H-indole 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-aryl(indol-3-yl)glyoxamides as antitumor agents

  摘要：

  The synthesis and study of the structure-activity relationships of cytotoxic compounds based on N-pyridinyl or N-aryl-2-(1-benzylindol-3-yl)glyoxamide skeleton, represented by the lead structures D-24241 and D-24851, are described. The presence of N-(pyridin-4-yl) moiety was crucial for activity and 2-[1(4-chloro-3-nitrobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide (55), the most potent derivative, showed IC(50) = 39 nM, 51 nM and 11 nM against HeLa/KB (human cervix carcinoma), L1210 (murine leukemia) and SKOV3 (human ovarian carcinoma) cell lines proliferation assay, respectively, as active as the lead compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.048
• 作为产物：
  描述：

  吲哚 、 1-(溴甲基)-4-氯-2-甲氧基苯 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以48%的产率得到1-(4-chloro-2-methoxybenzyl)-1H-indole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-aryl(indol-3-yl)glyoxamides as antitumor agents

  摘要：

  The synthesis and study of the structure-activity relationships of cytotoxic compounds based on N-pyridinyl or N-aryl-2-(1-benzylindol-3-yl)glyoxamide skeleton, represented by the lead structures D-24241 and D-24851, are described. The presence of N-(pyridin-4-yl) moiety was crucial for activity and 2-[1(4-chloro-3-nitrobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide (55), the most potent derivative, showed IC(50) = 39 nM, 51 nM and 11 nM against HeLa/KB (human cervix carcinoma), L1210 (murine leukemia) and SKOV3 (human ovarian carcinoma) cell lines proliferation assay, respectively, as active as the lead compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.048