1-[(4-氯苯基)甲基]-5-甲氧基-2-(4-甲氧基苯基)-3-甲基吲哚 | 104598-91-6

• 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
• 中文名称: 1-[(4-氯苯基)甲基]-5-甲氧基-2-(4-甲氧基苯基)-3-甲基吲哚
• 英文名称: 1-[(4-chlorophenyl)methyl]-5-methoxy-2-(4-methoxyphenyl)-3-methylindole
• CAS: 104598-91-6
• 化学式: C₂₄H₂₂ClNO₂
• 分子量: 391.897
• InChiKey: UNVXMLGVKOENMF-UHFFFAOYSA-N

物化性质

• 熔点：
  121-123 °C(Solv: ethanol (64-17-5))
• 沸点：
  564.9±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(4-氯苯基)甲基]-5-甲氧基-2-(4-甲氧基苯基)-3-甲基吲哚 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [4-[5-acetyloxy-1-[(4-chlorophenyl)methyl]-3-methylindol-2-yl]phenyl] acetate
  参考文献：
  名称：

  2-Phenylindoles. Effect of N-benzylation on estrogen receptor affinity, estrogenic properties, and mammary tumor inhibiting activity

  摘要：

  Hydroxy-2-phenylindoles carrying substituted benzyl groups and similar substituents at the nitrogen were synthesized and tested for their ability to displace estradiol from its receptor. All of the derivatives tested exhibited high binding affinities for the calf uterine estrogen receptor, with RBA values ranging from 0.55 to 16 (estradiol 100). The mouse uterine weight tested revealed only low estrogenicity for this class of compounds. Several derivatives showed antiestrogenic activity with a maximum inhibition of estrone-stimulated uterine growth of 40%. Two of the compounds (6c, 21c) were tested for antitumor activity in dimethylbenanthracene- (DMBA-) induced estrogen-dependent rat mammary tumors. Only the 4-cyanobenzyl derivative 21c was active. After 4 weeks of treatment with 12 mg/kg (6 times/week), the average tumor area was decreased by 57% (control +204%). In vitro, an inhibitory effect of 21b was only observed with hormone-sensitive MCF-7 breast cancer cells but not with hormone-independent MDA-MB 231 cells. These results make a mode of action involving the estrogen receptor system likely.

  DOI：

  10.1021/jm00384a022
• 作为产物：
  描述：

  4-甲氧基苯肼盐酸盐 在 盐酸 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.5h， 生成 1-[(4-氯苯基)甲基]-5-甲氧基-2-(4-甲氧基苯基)-3-甲基吲哚
  参考文献：
  名称：

  作为GluK1 / GluK2受体非竞争性拮抗剂的2,3,5-三取代和1,2,3,5-四取代的吲哚的热光谱研究

  摘要：

  本文通过TG-DSC（空气中）和TG-FTIR（氮气中）技术报道了六种吲哚衍生物的热稳定性和热降解。还通过红外光谱对化合物进行了表征。另外，计算红外光谱并将其与实验数据进行比较。特别地，进行势能分布分析以分配IR信号。所研究的化合物的特征是在氧化性和惰性气氛中具有良好的热稳定性，这对潜在的医学应用至关重要。空气中的热重测量表明，化合物的分解过程分为两个或三个主要阶段。化合物的热降解之前是熔融过程。样品的热解是一个一步的过程。加上在氮气中进行的分析，记录气相产物的FTIR光谱。在气态产物的FTIR光谱上，仅存在水，二氧化碳和碳氧化物分子的谱带。如果吲哚衍生物含有p -氯苄基的取代基在位置1，苯甲醚，的频带p -chlorotoluene和氯苯也出现。

  DOI：

  10.1007/s10973-018-7146-6

文献信息

• Structural studies, homology modeling and molecular docking of novel non-competitive antagonists of GluK1/GluK2 receptors
  作者：Agnieszka A. Kaczor、Zbigniew Karczmarzyk、Andrzej Fruziński、Kalevi Pihlaja、Jari Sinkkonen、Kirsti Wiinämaki、Christiane Kronbach、Klaus Unverferth、Antti Poso、Dariusz Matosiuk

  DOI：10.1016/j.bmc.2013.12.013

  日期：2014.1

  Non-competitive ligands of kainate receptors have focused significant attention as medicinal compounds because they seem to be better tolerated than competitive antagonists and uncompetitive blocker of these receptors. Here we present structural studies (X-ray structure determination, NMR and MS spectra) of novel indole-derived non-competitive antagonists of GluK1/GluK2 receptors, homology models of GluK1 and GluK2 receptors based on novel AMPA receptor template as well as molecular docking of ligands to their molecular targets. We find that the allosteric site is in the receptor transduction domain, in one receptor subunit, not between the two subunits as it was indicated by our earlier studies. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel Non-Competitive Antagonists of Kainate GluK1/GluK2 Receptors
  作者：Agnieszka Anna Kaczor、Christiane Kronbach、Klaus Unverferth、Kalevi Pihlaja、Kirsti Wiinamaki、Jari Sinkkonen、Urszula Kijkowska-Murak、Tomasz Wrobel、Tomasz Stachal、Dariusz Matosiuk

  DOI：10.2174/157018012804586978

  日期：2012.12.1
• VON ANGERER E.; STROHMEIER J., J. MED. CHEM., 30,(1987) N 1, 131-136
  作者：VON ANGERER E.、 STROHMEIER J.

  DOI：——

  日期：——
• Thermal and spectroscopic studies of 2,3,5-trisubstituted and 1,2,3,5-tetrasubstituted indoles as non-competitive antagonists of GluK1/GluK2 receptors
  作者：Agata Bartyzel、Agnieszka A. Kaczor、Halina Głuchowska、Monika Pitucha、Tomasz M. Wróbel、Dariusz Matosiuk

  DOI：10.1007/s10973-018-7146-6

  日期：2018.8

  TG-DSC (in air) and TG-FTIR (in nitrogen) techniques. The compounds were also characterized by infrared spectroscopy. In addition, IR spectra were calculated and compared with the experimental data. In particular, the potential energy distribution analysis was performed to assign IR signals. The studied compounds are characterized by good thermal stability in oxidizing and inert atmospheres which is

  本文通过TG-DSC（空气中）和TG-FTIR（氮气中）技术报道了六种吲哚衍生物的热稳定性和热降解。还通过红外光谱对化合物进行了表征。另外，计算红外光谱并将其与实验数据进行比较。特别地，进行势能分布分析以分配IR信号。所研究的化合物的特征是在氧化性和惰性气氛中具有良好的热稳定性，这对潜在的医学应用至关重要。空气中的热重测量表明，化合物的分解过程分为两个或三个主要阶段。化合物的热降解之前是熔融过程。样品的热解是一个一步的过程。加上在氮气中进行的分析，记录气相产物的FTIR光谱。在气态产物的FTIR光谱上，仅存在水，二氧化碳和碳氧化物分子的谱带。如果吲哚衍生物含有p -氯苄基的取代基在位置1，苯甲醚，的频带p -chlorotoluene和氯苯也出现。
• 2-Phenylindoles. Effect of N-benzylation on estrogen receptor affinity, estrogenic properties, and mammary tumor inhibiting activity
  作者：Erwin Von Angerer、Josef Strohmeier

  DOI：10.1021/jm00384a022

  日期：1987.1

  Hydroxy-2-phenylindoles carrying substituted benzyl groups and similar substituents at the nitrogen were synthesized and tested for their ability to displace estradiol from its receptor. All of the derivatives tested exhibited high binding affinities for the calf uterine estrogen receptor, with RBA values ranging from 0.55 to 16 (estradiol 100). The mouse uterine weight tested revealed only low estrogenicity for this class of compounds. Several derivatives showed antiestrogenic activity with a maximum inhibition of estrone-stimulated uterine growth of 40%. Two of the compounds (6c, 21c) were tested for antitumor activity in dimethylbenanthracene- (DMBA-) induced estrogen-dependent rat mammary tumors. Only the 4-cyanobenzyl derivative 21c was active. After 4 weeks of treatment with 12 mg/kg (6 times/week), the average tumor area was decreased by 57% (control +204%). In vitro, an inhibitory effect of 21b was only observed with hormone-sensitive MCF-7 breast cancer cells but not with hormone-independent MDA-MB 231 cells. These results make a mode of action involving the estrogen receptor system likely.