methyl 6-acetamido-4-(cyclohexylmethoxy)-1H-indole-2-carboxylate | 1427164-31-5

• 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: methyl 6-acetamido-4-(cyclohexylmethoxy)-1H-indole-2-carboxylate
• 英文别名: 4-cyclohexylmethoxy-6-acetylaminoindole-2-carboxylic acid methyl ester
• CAS: 1427164-31-5
• 化学式: C₁₉H₂₄N₂O₄
• 分子量: 344.411
• InChiKey: FJNIKMSCDCPNTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-acetamido-4-(cyclohexylmethoxy)-1H-indole-2-carboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以73%的产率得到methyl 6-amino-4-cyclohexylmethoxy-1H-indole-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives

  摘要：

  Based on the chemical structure of Pyrroloquinoline quinone (PQQ), a novel class of indole-2-carboxylate derivatives was designed, synthesized and assayed for antiproliferative activity in cancer cells in vitro. The biological results showed that some derivatives exhibited significant antiproliferative activity against HepG2, A549 and MCF7 cells. Notably, the novel compounds, methyl 6-amino-4-cyclohexylmethoxy-1H-indole-2-carboxylate (6e) and methyl 4-isopropoxy-6-methoxy-1H-indole-2-carboxylate (9l) exhibited more potent antiproliferative activity than the reference drugs PQQ and etoposide in vitro, with IC50 values ranging from 3.78 ± 0.58 to 24.08 ± 1.76 μM. Further biological assay showed that both compounds 6e and 9l increased ROS generation dose-dependently, and induced PARP cleavage in A549 cells. Consequently, 6e and 9l appeared as promising anticancer lead compounds for further optimization.

  DOI：

  10.1016/j.ejmech.2014.05.043
• 作为产物：
  描述：

  对乙酰氨基-邻甲氧基苯甲酸甲酯 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 16.0h， 生成 methyl 6-acetamido-4-(cyclohexylmethoxy)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives

  摘要：

  Based on the chemical structure of Pyrroloquinoline quinone (PQQ), a novel class of indole-2-carboxylate derivatives was designed, synthesized and assayed for antiproliferative activity in cancer cells in vitro. The biological results showed that some derivatives exhibited significant antiproliferative activity against HepG2, A549 and MCF7 cells. Notably, the novel compounds, methyl 6-amino-4-cyclohexylmethoxy-1H-indole-2-carboxylate (6e) and methyl 4-isopropoxy-6-methoxy-1H-indole-2-carboxylate (9l) exhibited more potent antiproliferative activity than the reference drugs PQQ and etoposide in vitro, with IC50 values ranging from 3.78 ± 0.58 to 24.08 ± 1.76 μM. Further biological assay showed that both compounds 6e and 9l increased ROS generation dose-dependently, and induced PARP cleavage in A549 cells. Consequently, 6e and 9l appeared as promising anticancer lead compounds for further optimization.

  DOI：

  10.1016/j.ejmech.2014.05.043

文献信息

• Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives
  作者：Xing-yue Ji、Si-tu Xue、Yue-chen Zhan、Jia-jia Shen、Lin-tao Wu、Jie Jin、Zhen Wang、Zhuo-rong Li

  DOI：10.1016/j.ejmech.2014.05.043

  日期：2014.8

  Based on the chemical structure of Pyrroloquinoline quinone (PQQ), a novel class of indole-2-carboxylate derivatives was designed, synthesized and assayed for antiproliferative activity in cancer cells in vitro. The biological results showed that some derivatives exhibited significant antiproliferative activity against HepG2, A549 and MCF7 cells. Notably, the novel compounds, methyl 6-amino-4-cyclohexylmethoxy-1H-indole-2-carboxylate (6e) and methyl 4-isopropoxy-6-methoxy-1H-indole-2-carboxylate (9l) exhibited more potent antiproliferative activity than the reference drugs PQQ and etoposide in vitro, with IC50 values ranging from 3.78 ± 0.58 to 24.08 ± 1.76 μM. Further biological assay showed that both compounds 6e and 9l increased ROS generation dose-dependently, and induced PARP cleavage in A549 cells. Consequently, 6e and 9l appeared as promising anticancer lead compounds for further optimization.