methyl 5-methoxy-1-methyl-1H-indole-3-carboxylate | 172595-71-0

• 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: methyl 5-methoxy-1-methyl-1H-indole-3-carboxylate
• 英文别名: methyl 5-methoxy-1-methylindole-3-carboxylate
• CAS: 172595-71-0
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: NEVGJVIWXVBTQE-UHFFFAOYSA-N

物化性质

• 沸点：
  359.5±22.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-methoxy-1-methyl-1H-indole-3-carboxylate 在 盐酸 、 tin 、 lithium aluminium tetrahydride 、 硝酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 3-(hydroxymethyl)-5-methoxy-1-methylindole-4,7-dione
  参考文献：
  名称：

  Bexarotene prodrugs: Targeting through cleavage by NQO1 (DT-diaphorase)

  摘要：

  Bexarotene, a retinoid X receptor (RXR) agonist, is being tested as a potential disease modifying treatment for neurodegenerative conditions. To limit the peripheral exposure of bexarotene and release it only in the affected areas of the brain, we designed a prodrug strategy based on the enzyme NAD( P) H/quinone oxidoreductase (NQO1) that is elevated in neurodegenerative diseases. A series of indolequinones (known substrates of NQO1) was synthesized and coupled to bexarotene. Bexarotene-3(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione ester 7a was cleaved best by NQO1. The prodrugs are not cleaved by esterase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.003
• 作为产物：
  描述：

  吲哚-3-甲酸甲酯 在 aluminum (III) chloride 、 disodium hydrogenphosphate 、 间氯过氧苯甲酸 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 二甲基亚砜 、 丙酮 为溶剂， 反应 17.0h， 生成 methyl 5-methoxy-1-methyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Bexarotene prodrugs: Targeting through cleavage by NQO1 (DT-diaphorase)

  摘要：

  Bexarotene, a retinoid X receptor (RXR) agonist, is being tested as a potential disease modifying treatment for neurodegenerative conditions. To limit the peripheral exposure of bexarotene and release it only in the affected areas of the brain, we designed a prodrug strategy based on the enzyme NAD( P) H/quinone oxidoreductase (NQO1) that is elevated in neurodegenerative diseases. A series of indolequinones (known substrates of NQO1) was synthesized and coupled to bexarotene. Bexarotene-3(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione ester 7a was cleaved best by NQO1. The prodrugs are not cleaved by esterase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.003

文献信息

• Development of Bisindole-Substituted Aminopyrazoles as Novel GSK-3β Inhibitors with Suppressive Effects against Microglial Inflammation and Oxidative Neurotoxicity
  作者：Jian-Guo Liu、Danfeng Zhao、Qi Gong、Fengxia Bao、Wen-Wen Chen、Haiyan Zhang、Ming-Hua Xu

  DOI：10.1021/acschemneuro.0c00520

  日期：2020.10.21

  kinase-3β (GSK-3β) inactivation-centric agents with polypharmacological profiles is increasingly recognized as a promising therapeutic strategy against the multifactorial etiopathology of Alzheimer’s disease (AD). In this respect, a series of disubstituted aminopyrazole derivatives were designed and synthesized as a new class of GSK-3β inhibitors. Most of these derivatives possess GSK-3β inhibitory activities

  开发具有多种药理学特征的以糖原合酶激酶-3β (GSK-3β) 失活为中心的药物越来越被认为是一种有前途的治疗策略，可对抗阿尔茨海默病 (AD) 的多因素病因。在这方面，设计并合成了一系列二取代氨基吡唑衍生物作为一类新的GSK-3β抑制剂。这些衍生物大多具有 GSK-3β 抑制活性，IC 50值在微摩尔范围内，其中双吲哚取代的氨基吡唑衍生物6h表现出中等 GSK-3β 抑制作用（IC 50= 1.76 ± 0.19 μM)，以及对脂多糖 (LPS) 诱导的 BV-2 细胞神经胶质炎症和谷氨酸诱导的 HT-22 细胞氧化神经毒性的缓解作用。进一步的体内研究表明，化合物6h具有有效的抗炎作用，通过显示 LPS 注射小鼠脑中的小胶质细胞活化和星形胶质细胞增殖显着降低。总体而言， 6h对疾病网络的多种功能障碍的同时调节突出了这种结构独特的双吲哚取代的氨基吡唑可能是发现新的治疗药物以解决 AD 和其他
• Cyanopyrrolidines useful for the treatment of inter alia metabolic syndrome
  申请人：SANWA KAGAKU KENKYUSHO CO., LTD.

  公开号：EP1595866B1

  公开（公告）日：2016-06-08
• 10.1691/ph.2017.7722
  作者：Hu, Yuanyuan、Ruan, Wenchen、Gao, Anhui、Zhou, Yubo、Gao, Lixin、Xu, Meng、Gao, Jianrong、Ye, Qing、Li, Jia、Pang, Tao

  DOI：10.1691/ph.2017.7722

  日期：——
• Synthesis of Indole-3-carboxylic Acid Derivatives by Pd(0)-Catalyzed Intramolecular α-Arylation of β-(2-Iodoanilino) Esters
  作者：Daniel Solé、Olga Serrano

  DOI：10.1021/jo800034m

  日期：2008.3.1

  beta-(2-Iodoanilino) esters undergo intramolecular alpha-arylation in the presence of Pd(PPh3)(4) and potassium phenoxide. The reaction is a useful methodology for the preparation of indole-3-carboxylic acid ester derivatives.
• Construction of indoloquinolinones via Pd(II)-catalyzed tandem C C/C N bond formation: application to the total synthesis of isocryptolepine
  作者：Xuebing Chen、Peng Sun、Jinyi Xu、Xiaoming Wu、Lingyi Kong、Hequan Yao、Aijun Lin

  DOI：10.1016/j.tetlet.2014.11.008

  日期：2014.12