7-甲氧基-1H-吲哚-2-羧酸甲酯 | 84638-71-1

• 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
• 中文名称: 7-甲氧基-1H-吲哚-2-羧酸甲酯
• 英文名称: methyl 7-methoxy-1H-indole-2-carboxylate
• CAS: 84638-71-1
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: OMKLIYMSJTUMRD-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  370.1±22.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-甲氧基-1H-吲哚-2-羧酸甲酯 在 sodium hydroxide 作用下， 以96%的产率得到7-甲氧基吲哚-2-羧酸
  参考文献：
  名称：

  Effects of Indole Fatty Alcohols on the Differentiation of Neural Stem Cell Derived Neurospheres

  摘要：

  In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared. 13C (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.

  DOI：

  10.1021/jm0493616
• 作为产物：
  描述：

  (Z)-methyl 3-(2-amino-3-methoxyphenyl)-2-bromoacrylate 在 三乙烯二胺 、 copper(l) iodide 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以86%的产率得到7-甲氧基-1H-吲哚-2-羧酸甲酯
  参考文献：
  名称：

  CuI-catalyzed intramolecular cyclization of 3-(2-aminophenyl)-2-bromoacrylate: synthesis of 2-carboxyindoles

  摘要：

  A new approach was described for the synthesis of substituted 2-carboxyindole using 3-(2-aminophenyl)-2-bromo-acrylates through a CuI-catalyzed intramolecular coupling. The reactions were mild, rapid and with good to excellent yields. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.048

文献信息

• Design, synthesis and biological evaluation of 2-alkoxycarbonyl-3-anilinoindoles as a new class of potent inhibitors of tubulin polymerization
  作者：Romeo Romagnoli、Filippo Prencipe、Paola Oliva、Maria Kimatrai Salvador、Andrea Brancale、Salvatore Ferla、Ernest Hamel、Giampietro Viola、Roberta Bortolozzi、Leentje Persoons、Jan Balzarini、Sandra Liekens、Dominique Schols

  DOI：10.1016/j.bioorg.2020.103665

  日期：2020.4

  A new class of inhibitors of tubulin polymerization based on the 2-alkoxycarbonyl-3-(3',4',5'-trimethoxyanilino)indole molecular skeleton was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization and cell cycle effects. The results presented show that the methoxy substitution and location on the indole nucleus plays an important role in inhibition of cell growth

  合成了基于2-烷氧基羰基-3-（3'，4'，5'-三甲氧基苯胺基）吲哚分子骨架的新型微管蛋白聚合抑制剂，并评估了其抗增殖活性，抑制微管蛋白聚合和细胞周期的作用。给出的结果表明，甲氧基取代和吲哚核上的位置在抑制细胞生长中起着重要作用，最优选的取代基是在C-6处。另外，期望在吲哚核的2-位具有小尺寸的酯官能团（甲氧基/乙氧基羰基）。同样，被甲基，乙基或正丙基烷基化或在N-1吲哚氮上具有苄基部分的类似物保留的活性与在母体N-1H类似物中观察到的活性相同。
• Indole derivatives pharmaceutical preparations based thereon, and
  申请人：Schering Aktiengesellschaft

  公开号：US04835175A1

  公开（公告）日：1989-05-30

  Indole derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen, alkyl of 1-6 carbon atoms, or benzyl R.sub.2 is hydrogen, alkyl of up to 4 carbon atoms, free or esterified hydroxyalkyl of up to 4 carbon atoms, or free, amidated or esterified carboxy or carboxyalkyl, R.sub.3 is hydrogen or alkyl containing 1-6 carbon atoms, R.sub.4 is hydrogen or alkyl containing 1-6 carbon atoms and R.sub.5 is hydrogen, or alkyl, alkenyl, or cycloalkyl, all of which per se contain up to 6 carbon atoms, and all of which are optionally substituted by a free or esterified carboxy group or by an optionally substituted phenyl group; or a polymethylene group of up to 8 carbon atoms linking the first indole residue to a second indole residue of Formula Ia ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as defined above, and the physiologically acceptable salts thereof with acids and, optionally, their alkali metal and alkaline earth metal salts, possess valuable pharmacological properties, such as stimulating .beta.-receptors and prevention of premature labor, are described.

  Formula I中的吲哚衍生物##STR1##其中R.sub.1是氢，1-6个碳原子的烷基，或苄基R.sub.2是氢，最多4个碳原子的烷基，自由或酯化的最多4个碳原子的羟基烷基，或自由的，酰化的或酯化的羧基或羧基烷基，R.sub.3是氢或含有1-6个碳原子的烷基，R.sub.4是氢或含有1-6个碳原子的烷基，R.sub.5是氢，或烷基，烯基，或环烷基，这些本身包含最多6个碳原子，并且这些都可以选择地被自由或酯化的羧基或通过一个可选择地被取代的苯基团取代；或者是一个最多含有8个碳原子的聚亚甲基基团，将第一个吲哚残基与Formula Ia的第二个吲哚残基连接起来##STR2##其中R.sub.1，R.sub.2，R.sub.3和R.sub.4如上所定义，并且其与酸的生理上可接受的盐，以及可选地其碱金属和碱土金属盐，具有有价值的药理特性，如刺激β-受体和预防早产。
• Continuous flow thermolysis of azidoacrylates for the synthesis of heterocycles and pharmaceutical intermediates
  作者：Alexander G. O'Brien、François Lévesque、Peter H. Seeberger

  DOI：10.1039/c0cc04481d

  日期：——

  An efficient, safe and scalable procedure for the continuous flow thermolysis of azidoacrylates to yield indoles has been developed and was applied to the synthesis of related heterocycles. The scalability of the process was demonstrated in the continuous flow synthesis of a precursor to the DAAO inhibitor 4H-furo[3,2-b]pyrrole-5-carboxylic acid.

  已经开发了一种有效，安全和可扩展的方法，用于叠氮丙烯酸酯的连续流热解以生成吲哚，并将其用于相关杂环的合成。该方法的可扩展性在DAAO抑制剂4H-呋喃[3,2-b]吡咯-5-羧酸的前体的连续流动合成中得到证明。
• [EN] ARYL AND HETEROARYL-CARBOXAMIDE SUBSTITUTED HETEROARYL COMPOUNDS AS TYK2 INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROARYLE SUBSTITUÉS PAR ARYLE ET HÉTÉROARYLE-CARBOXAMIDE UTILES EN TANT QU'INHIBITEURS DE TYK2
  申请人：ALMIRALL SA

  公开号：WO2021204626A1

  公开（公告）日：2021-10-14

  Novel carboxamide substituted compounds of Formula (I) are disclosed; as well as processes for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Tyrosine Kinase 2 (Tyk2).

  公开了一种化合物，其为新颖的羧酰胺取代化合物，化学式为（I）；以及其制备方法，包含它们的药物组成物和它们作为酪氨酸激酶2（Tyk2）抑制剂在治疗中的用途。
• Indole derivatives and drugs containing the same
  申请人：Luu Bang

  公开号：US20050261357A1

  公开（公告）日：2005-11-24

  An indole derivative represented by the following general formula (1): wherein at least one of R 1 , R 2 , R 3 , and R 4 represents an alkoxy group containing 1 to 20 carbon atoms, and other groups of the R 1 , R 2 , R 3 , and R 4 represent hydrogen, an alkyl group containing 1 to 6 carbon atoms, acetyl group, or hydroxyl group; and either one of X and Y represents —(CH 2 ) n OH wherein n is an integer of 0 to 30, and the other one of the X and Y represents hydrogen atom; or a salt thereof; and a drug and an agent for promoting differentiation of a stem cell containing such indole derivative or its salt as an effective component. The indole derivative (1) of the present invention has action of inducing differentiation of neural stem cell specifically into a neuron, and this indole derivative is useful as a prophylactic or therapeutic drug for brain dysfunction or neuropathy caused by loss or degeneration of the neuron.

  以下是一种由下述通式（1）表示的吲哚衍生物: 其中，R1、R2、R3和R4中至少有一个表示含有1到20个碳原子的烷氧基，而R1、R2、R3和R4的其他基团则表示氢、含有1到6个碳原子的烷基、乙酰基或羟基；X和Y中的一个表示—（CH2）nOH，其中n为0到30的整数，而X和Y的另一个表示氢原子；或其盐；以及包含这种吲哚衍生物或其盐作为有效成分的药物和促进干细胞分化的药剂。本发明的吲哚衍生物（1）具有特异性诱导神经干细胞分化为神经元的作用，因此这种吲哚衍生物可用作预防或治疗因神经元丧失或退化引起的脑功能障碍或神经病变的药物。