2-[(5-methoxy-1H-indol-3-yl)methyl]-1H-indole-3-carbaldehyde | 1622429-29-1

• 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: 2-[(5-methoxy-1H-indol-3-yl)methyl]-1H-indole-3-carbaldehyde
• CAS: 1622429-29-1
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: YSCCCRCXQOQKCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl 2-(3-methoxyprop-1-ynyl)phenylcarbamate 在 sodium carbonate 、 platinum(II) chloride 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 2-[(5-methoxy-1H-indol-3-yl)methyl]-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3′-diindolylmethanes as agonists of aryl hydrocarbon receptor

  摘要：

  Recent studies suggest that arylhydrocarbon receptor (AhR) may be a target for a number of diseases. Natural product malassezin is a AhR agonist with an interesting 2,3'-diindolylmethane skeleton. We have prepared a series of analogues of natural product malassezin using our recently developed method and tested the activity of these analogues against AhR in a cell-based assay. We found that a methyl substituent at 1'-N can significantly increase the activity and the 2-formyl group is not critical for some diindolylmethanes.

  DOI：

  10.1016/j.bmcl.2014.06.009

文献信息

• SYNTHESIS OF DIINDOLYLMETHANES AND INDOLO[3,2-B]CARBAZOLES, COMPOUNDS FORMED THEREBY, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20160039754A1

  公开（公告）日：2016-02-11

  Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or unsubstituted indol or a substituted or unsubstituted pyrrole, in the presence of a metal-containing catalyst, for a time and at a temperature to cause an annulation/arylation cascade reaction that yields a diindolylmethane or a indolyl/pyrrolylmethane. The resulting compounds are effective to modulate activity of arylhydrocarbon receptors, to inhibit activity of PCSK9, and to stimulate secretion of glucagon-like peptide 1 in mammals.

  描述了一种制备二吲哚基甲烷和吲哚基/吡咯基甲烷的方法。该方法包括以下步骤：在金属催化剂的存在下，使包含芳基炔丙基部分和胺保护的、取代的或未取代的苯胺部分的醚与取代的或未取代的吲哚或取代的或未取代的吡咯接触，接触一段时间和温度，以引发环化/芳基化级联反应，从而产生二吲哚基甲烷或吲哚基/吡咯基甲烷。所得化合物能有效调节芳基烃受体的活性，抑制PCSK9的活性，并刺激哺乳动物胰高血糖素样肽1的分泌。
• Synthesis of diindolylmethanes and indolo[3,2-b]carbazoles, compounds formed thereby, and pharmaceutical compositions containing them
  申请人：Wisconsin Alumni Research Foundation

  公开号：US10730833B2

  公开（公告）日：2020-08-04

  Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or unsubstituted indol or a substituted or unsubstituted pyrrole, in the presence of a metal-containing catalyst, for a time and at a temperature to cause an annulation/arylation cascade reaction that yields a diindolylmethane or a indolyl/pyrrolylmethane. The resulting compounds are effective to modulate activity of arylhydrocarbon receptors, to inhibit activity of PCSK9, and to stimulate secretion of glucagon-like peptide 1 in mammals.

  描述了一种制造二吲哚甲烷和吲哚基/吡咯基甲烷的方法，该方法包括以下步骤：将包含芳基丙炔基和胺保护的取代或未取代的苯胺基的醚与取代或未取代的吲哚或取代或未取代的吡咯接触、在含金属催化剂存在下，在一定时间和温度下进行环化/芳基化级联反应，生成二吲哚基甲烷或吲哚基/吡咯基甲烷。所得化合物可有效调节芳基烃受体的活性，抑制 PCSK9 的活性，并刺激哺乳动物分泌胰高血糖素样肽 1。
• US9969686B2
  申请人：——

  公开号：US9969686B2

  公开（公告）日：2018-05-15
• Synthesis and biological evaluation of 2,3′-diindolylmethanes as agonists of aryl hydrocarbon receptor
  作者：Gabrielle N. Winston-McPherson、Dongxu Shu、Weiping Tang

  DOI：10.1016/j.bmcl.2014.06.009

  日期：2014.8

  Recent studies suggest that arylhydrocarbon receptor (AhR) may be a target for a number of diseases. Natural product malassezin is a AhR agonist with an interesting 2,3'-diindolylmethane skeleton. We have prepared a series of analogues of natural product malassezin using our recently developed method and tested the activity of these analogues against AhR in a cell-based assay. We found that a methyl substituent at 1'-N can significantly increase the activity and the 2-formyl group is not critical for some diindolylmethanes.