6-methoxy-2-(4-methylphenyl)indole | 258336-47-9

• 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-2-(4-methylphenyl)indole
• 英文别名: 6-Methoxy-2-(4-tolyl)indole；6-methoxy-2-(4-methylphenyl)-1H-indole
• CAS: 258336-47-9
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: WQHPNDFRBQXGJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 6-methoxy-2-(4-methylphenyl)indole 在 三氯氧磷 作用下， 反应 3.0h， 以60%的产率得到6-Methoxy-2-(4-methylphenyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells

  摘要：

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.030
• 作为产物：
  描述：

  间氨基苯甲醚 、 2-溴-4'-甲基苯乙酮 在 N,N-二甲基苯胺 作用下， 以 xylene 为溶剂， 以42%的产率得到6-methoxy-2-(4-methylphenyl)indole
  参考文献：
  名称：

  Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells

  摘要：

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.030

文献信息

• Hydrophilic compounds for optically active devices
  申请人：MERCK PATENT GMBH

  公开号：US11014900B2

  公开（公告）日：2021-05-25

  The present invention relates to novel compounds, particularly to compounds comprising a photoactive unit, said novel compounds being particularly suitable for compositions and ophthalmic devices as well as to compositions and ophthalmic devices comprising such compounds.

  本发明涉及新型化合物，特别是包含光活性单元的化合物，所述新型化合物尤其适用于组合物和眼科设备，以及包含此类化合物的组合物和眼科设备。
• HYDROPHILIC COMPOUNDS FOR OPTICALLY ACTIVE DEVICES
  申请人：MERCK PATENT GMBH

  公开号：US20200231559A1

  公开（公告）日：2020-07-23

  The present invention relates to novel compounds, particularly to compounds comprising a photoactive unit, said novel compounds being particularly suitable for compositions and ophthalmic devices as well as to compositions and ophthalmic devices comprising such compounds.
• Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells
  作者：Doris Kaufmann、Michaela Pojarová、Susanne Vogel、Renate Liebl、Robert Gastpar、Dietmar Gross、Tsuyuki Nishino、Tobias Pfaller、Erwin von Angerer

  DOI：10.1016/j.bmc.2007.05.030

  日期：2007.8

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.