5-methoxy-1-(4-methoxybenzyl)-indole-3-carboxaldehyde | 1226139-58-7

• 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: 5-methoxy-1-(4-methoxybenzyl)-indole-3-carboxaldehyde
• 英文别名: 5-methoxy-1-[(4-methoxyphenyl)methyl]indole-3-carbaldehyde
• CAS: 1226139-58-7
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: BYRJDAWNNQSEET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1H-吲哚-3-羧酸肼 、 5-methoxy-1-(4-methoxybenzyl)-indole-3-carboxaldehyde 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以85%的产率得到N-[[5-methoxy-1-[(4-methoxyphenyl)methyl]indol-3-yl]methylideneamino]-1H-indole-3-carboxamide
  参考文献：
  名称：

  Novel bis(indolyl)hydrazide–hydrazones as potent cytotoxic agents

  摘要：

  A series of bis(indolyl) hydrazide-hydrazones 5a-n were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-carboxaldehyde 2 with indole-3-carbohydrazide 4 in presence of catalytic amount of acetic acid afforded 5a-n in good yields. Among the synthesized bis(indolyl) hydrazide-hydrazones, the compound 5b with N-(p-chlorobenzyl) and bromo substituents was found to be the most potent against multiple cancer cell lines (IC(50) = 1.0 mu M, MDA-MB-231). The compound 5k exhibited selective cytotoxicity against breast cancer cell line MCF7 (IC(50) = 3.1 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.031
• 作为产物：
  描述：

  5-甲氧基吲哚-3-甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 生成 5-methoxy-1-(4-methoxybenzyl)-indole-3-carboxaldehyde
  参考文献：
  名称：

  Novel bis(indolyl)hydrazide–hydrazones as potent cytotoxic agents

  摘要：

  A series of bis(indolyl) hydrazide-hydrazones 5a-n were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-carboxaldehyde 2 with indole-3-carbohydrazide 4 in presence of catalytic amount of acetic acid afforded 5a-n in good yields. Among the synthesized bis(indolyl) hydrazide-hydrazones, the compound 5b with N-(p-chlorobenzyl) and bromo substituents was found to be the most potent against multiple cancer cell lines (IC(50) = 1.0 mu M, MDA-MB-231). The compound 5k exhibited selective cytotoxicity against breast cancer cell line MCF7 (IC(50) = 3.1 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.031

文献信息

• Design and synthesis of bis(indolyl)ketohydrazide-hydrazones: Identification of potent and selective novel tubulin inhibitors
  作者：Mukund P. Tantak、Linus Klingler、V. Arun、Anil Kumar、Rachna Sadana、Dalip Kumar

  DOI：10.1016/j.ejmech.2017.04.078

  日期：2017.8

  A novel series of ketohydrazide-hydrazones as analogues of naturally occurring coscinamides has been synthesized and evaluated for their anticancer activity against five cancer cell lines. Of the twenty synthesized ketohydrazide-hydrazones, compounds, 21c, 21f, 21g, 21k and 21o showed cytotoxic effects (less than 50% cell survival) against multiple cancer cell lines when tested at a final concentration of 10 mu M. IC50 of three compounds 21f, 21k and 21o was determined to be less than 5 mu M for all tested cancer cell lines. Compound 21k exhibited significant anticancer activity against MCF-7, MDA-MB-231, HCT-116 and JURKAT cancer cell lines with IC50 values of 0.8 mu M, 0.50 mu M, 0.15 mu M, and 0.22 mu M, respectively. Also, 21k was found to be more selectively cytotoxic against tumor cells when compared to normal cells. Preliminary mechanism of action studies indicated that the most active compound 21k induced caspase-dependent apoptosis in cells. 21k arrests cell cycle in G2/M phase by inhibiting of tubulin polymerization (IC50 = 0.6 mu M). (C) 2017 Elsevier Masson SAS. All rights reserved.
• Novel bis(indolyl)hydrazide–hydrazones as potent cytotoxic agents
  作者：Dalip Kumar、N. Maruthi Kumar、Soumitra Ghosh、Kavita Shah

  DOI：10.1016/j.bmcl.2011.11.031

  日期：2012.1

  A series of bis(indolyl) hydrazide-hydrazones 5a-n were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-carboxaldehyde 2 with indole-3-carbohydrazide 4 in presence of catalytic amount of acetic acid afforded 5a-n in good yields. Among the synthesized bis(indolyl) hydrazide-hydrazones, the compound 5b with N-(p-chlorobenzyl) and bromo substituents was found to be the most potent against multiple cancer cell lines (IC(50) = 1.0 mu M, MDA-MB-231). The compound 5k exhibited selective cytotoxicity against breast cancer cell line MCF7 (IC(50) = 3.1 mu M). (C) 2011 Elsevier Ltd. All rights reserved.