methyl 4-(1H-indol-1-yl)-3-methoxybenzoate | 1269834-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-(1H-indol-1-yl)-3-methoxybenzoate
• CAS: 1269834-28-7
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: AOLKMYAQPCYLPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  21.0
• 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：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(1H-indol-1-yl)-3-methoxybenzoate 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-(1H-indol-1-yl)-3-methoxybenzaldehyde
  参考文献：
  名称：

  Synthesis and preliminary evaluation of curcumin analogues as cytotoxic agents

  摘要：

  A series of curcumin analogues with different substituents at the 4-position of the phenyl group were synthesized and screened for in vitro cytotoxicity against a panel of human cancer cell lines. Several novel curcumin analogues, especially 32 and 34, exhibited selective and potent cytotoxic activity against human epidermoid carcinoma cell line A-431 and human glioblastoma cell line U-251, implying their specific potential in the chemoprevention and chemotherapy of skin cancer and glioma. The preliminary SAR information extracted from the results suggested that introduction of appropriate substituents to the 4'-positions could be a promising approach for the development of new cytotoxic curcumin analogues with special selectivity for A-431 and U-251 cell lines. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.12.020
• 作为产物：
  描述：

  3-甲氧基-4-氨基苯甲酸甲酯 在 copper(l) iodide 、 硫酸 、 potassium iodide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.5h， 生成 methyl 4-(1H-indol-1-yl)-3-methoxybenzoate
  参考文献：
  名称：

  Synthesis and preliminary evaluation of curcumin analogues as cytotoxic agents

  摘要：

  A series of curcumin analogues with different substituents at the 4-position of the phenyl group were synthesized and screened for in vitro cytotoxicity against a panel of human cancer cell lines. Several novel curcumin analogues, especially 32 and 34, exhibited selective and potent cytotoxic activity against human epidermoid carcinoma cell line A-431 and human glioblastoma cell line U-251, implying their specific potential in the chemoprevention and chemotherapy of skin cancer and glioma. The preliminary SAR information extracted from the results suggested that introduction of appropriate substituents to the 4'-positions could be a promising approach for the development of new cytotoxic curcumin analogues with special selectivity for A-431 and U-251 cell lines. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.12.020