ethyl 2-[4-[bis(1-methyl-1H-3-indolyl)methyl]phenoxy]acetate | 1361043-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-[4-[bis(1-methyl-1H-3-indolyl)methyl]phenoxy]acetate
• 英文别名: ethyl 2-(4-(bis(1-methyl-1H-indol-3-yl)methyl)phenoxy)acetate；ethyl 2-[4-[bis(1-methylindol-3-yl)methyl]phenoxy]acetate
• CAS: 1361043-96-0
• 化学式: C₂₉H₂₈N₂O₃
• 分子量: 452.553
• InChiKey: BNNXYVAGPFIMAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-[4-[bis(1-methyl-1H-3-indolyl)methyl]phenoxy]acetate 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-[4-[bis(1-methyl-1H-3-indolyl)methyl]phenoxymethyl]-5-(4-fluorophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,3,4-oxadiazole-linked bisindole derivatives as anticancer agents

  摘要：

  A series of ten 1,3,4-oxadiazole-linked bisindole derivatives have been synthesized. All compounds were evaluated for anticancer activity against four human cancer cell lines (MCF-7, KB, Colo-205, and A-549). Most of these new compounds exhibited significant anticancer activity as compared to etoposide. Compounds' GI(50) values range from < 0.1 to 3.9 mu M, while the positive control etoposide has a GI(50) in the range of 0.13-3.08 mu M in the cell lines employed. Among them, four compounds showed a higher activity than etoposide.

  DOI：

  10.1007/s00706-015-1448-1
• 作为产物：
  描述：

  吲哚 在 碘 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 ethyl 2-[4-[bis(1-methyl-1H-3-indolyl)methyl]phenoxy]acetate
  参考文献：
  名称：

  Indole-Based Fibrates as Potential Hypolipidemic and Antiobesity Agents

  摘要：

  Hypolipidemic and antiobesity effects of the newly synthesized indole-based fibrates were evaluated in Triton WR-1339 and high fat diet (HFD)-induced hyperlipidemic rats. Preliminary screening of all the synthesized compounds was done by using an acute model (Triton model), in which compounds 3f and 3l showed significant antidyslipidemic activity. Furthermore, these compounds 3f and 3l were found to induce significant weight loss in the visceral fat mass of HFD-fed hyperlipidemic rats without affecting the normal feeding behavior. Histological examination of the liver of rats supplemented with 3f and 3l revealed a significant decrease in steatosis when compared to the effect of the standard drug fenofibrate. Additional effects such as an increase in lecithin cholesterol acyl-transferase (LCAT) enzyme level and increased receptor mediated catabolism of I-131-low density lipoproteins (LDL) confirm and reinforce the efficacy of both of these compounds as a new class of dual-acting hypolipidemic and antiobesity agents.

  DOI：

  10.1021/jm201697v

文献信息

• Indole-Based Fibrates as Potential Hypolipidemic and Antiobesity Agents
  作者：Koneni V. Sashidhara、Manoj Kumar、Ravi Sonkar、Bhanu Shankar Singh、A. K. Khanna、Gitika Bhatia

  DOI：10.1021/jm201697v

  日期：2012.3.22

  Hypolipidemic and antiobesity effects of the newly synthesized indole-based fibrates were evaluated in Triton WR-1339 and high fat diet (HFD)-induced hyperlipidemic rats. Preliminary screening of all the synthesized compounds was done by using an acute model (Triton model), in which compounds 3f and 3l showed significant antidyslipidemic activity. Furthermore, these compounds 3f and 3l were found to induce significant weight loss in the visceral fat mass of HFD-fed hyperlipidemic rats without affecting the normal feeding behavior. Histological examination of the liver of rats supplemented with 3f and 3l revealed a significant decrease in steatosis when compared to the effect of the standard drug fenofibrate. Additional effects such as an increase in lecithin cholesterol acyl-transferase (LCAT) enzyme level and increased receptor mediated catabolism of I-131-low density lipoproteins (LDL) confirm and reinforce the efficacy of both of these compounds as a new class of dual-acting hypolipidemic and antiobesity agents.
• Synthesis and biological evaluation of 1,3,4-oxadiazole-linked bisindole derivatives as anticancer agents
  作者：Islavathu Hatti、Reddymasu Sreenivasulu、Surender Singh Jadav、Mohamed Jawed Ahsan、Rudraraju Ramesh Raju

  DOI：10.1007/s00706-015-1448-1

  日期：2015.10

  A series of ten 1,3,4-oxadiazole-linked bisindole derivatives have been synthesized. All compounds were evaluated for anticancer activity against four human cancer cell lines (MCF-7, KB, Colo-205, and A-549). Most of these new compounds exhibited significant anticancer activity as compared to etoposide. Compounds' GI(50) values range from < 0.1 to 3.9 mu M, while the positive control etoposide has a GI(50) in the range of 0.13-3.08 mu M in the cell lines employed. Among them, four compounds showed a higher activity than etoposide.