2-azido-3-(3'-methoxyphenyl)acrylic acid methyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-azido-3-(3'-methoxyphenyl)acrylic acid methyl ester
• 英文别名: (Z)-methyl 2-azido-3-(3-methoxyphenyl)acrylate；methyl 2-azide-3-(3-methoxyphenyl)-acrylate；methyl (Z)-2-azido-3-(3-methoxyphenyl)prop-2-enoate
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: BQHSWDGBCKUKGV-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azido-3-(3'-methoxyphenyl)acrylic acid methyl ester 在 喹啉 、 sodium hydroxide 、 铜 作用下， 以 xylene 为溶剂， 生成 5-甲氧基吲哚
  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：

  2-叠氮基乙酸甲酯 、 3-甲氧基苯甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以64%的产率得到2-azido-3-(3'-methoxyphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  叠氮基丙烯酸酯的连续流热解，用于合成杂环和医药中间体。

  摘要：

  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。

  DOI：

  10.1039/c0cc04481d

文献信息

• 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。
• 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。
• INDOLE DERIVATIVES AND DRUGS CONTAINING THE SAME
  申请人：Meiji Dairies Corporation

  公开号：EP1533299A1

  公开（公告）日：2005-05-25

  An indole derivative represented by the following general formula (1) : wherein at least one of R1, R2, R3, and R4 represents an alkoxy group containing 1 to 20 carbon atoms, and other groups of the R1, R2, R3, and R4 represent hydrogen, an alkyl group containing 1 to 6 carbon atoms, acetyl group, or hydroxyl group; and either one of X and Y represents -(CH2)nOH 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.

  由以下通式（1）代表的吲哚衍生物： 其中 R1、R2、R3 和 R4 中至少有一个代表含有 1 至 20 个碳原子的烷氧基，R1、R2、R3 和 R4 中的其他基团代表氢、含有 1 至 6 个碳原子的烷基、乙酰基或羟基；X和Y中的一个代表-(CH2)nOH，其中n为0至30的整数，X和Y中的另一个代表氢原子；或其盐；以及含有这种吲哚衍生物或其盐作为有效成分的促进干细胞分化的药物和制剂。 本发明的吲哚衍生物（1）具有诱导神经干细胞特异性分化为神经元的作用，这种吲哚衍生物可作为预防或治疗药物，用于治疗神经元缺失或变性引起的脑功能障碍或神经病变。
• 10.1002/chem.202401491
  作者：Crawford, Ruairi、Baumann, Marcus

  DOI：10.1002/chem.202401491

  日期：——

  can be accessed from simple vinyl azides in a chromoselective manner. The value of these entities is demonstrated through flow-based conversions to highly substituted dihydropyrimidines and pyrimidines that are privileged scaffolds in medicinal and materials chemistry.”

  “这项研究报告了一种高效且易于扩展的光化学途径进入氮嗪和相关光二聚体，可以从简单的乙烯基叠氮化物以色选择性方式获得。这些实体的价值通过基于流动的转化为高度取代的二氢嘧啶和嘧啶来证明，它们是药物和材料化学中的特权支架。
• Optimization of Chemical Functionalities of Indole-2-carboxamides To Improve Allosteric Parameters for the Cannabinoid Receptor 1 (CB1)
  作者：Leepakshi Khurana、Hamed I. Ali、Teresa Olszewska、Kwang H. Ahn、Aparna Damaraju、Debra A. Kendall、Dai Lu

  DOI：10.1021/jm5000112

  日期：2014.4.10

  5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type I receptor (CBI). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CBI: a critical chain length at the C3-position, an electron withdrawing group at the CS-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B. These significantly impact the binding affinity (K-B) and the binding cooperativity (alpha). A potent CB1 allosteric modulator 5-chloro-N-(4(dimethylamino)phenethyl)-3-propyl-1H-indole-2-carboxamide (12d) was identified. It exhibited a K-B of 259.3 nM with a strikingly high binding alpha of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (120 with a K-B of 89.1 nM, which is among the lowest K-B values obtained for any allosteric modulator of CB1. These positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced beta-arrestin mediated ERK/2 phosphorylation.