2-(7-甲氧基吲哚-1H-3-基)乙酸 | 850008-37-6

• 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: 2-(7-甲氧基吲哚-1H-3-基)乙酸
• 英文名称: 7-methoxyindoleacetic acid
• 英文别名: 2-(7-methoxy-1H-indol-3-yl)acetic acid；7-methoxyindole-3-acetic acid；(7-methoxy-indol-3-yl)-acetic acid；(7-Methoxy-indol-3-yl)-essigsaeure
• CAS: 850008-37-6
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: QAXDOPMLHZGKIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  62.3
• 氢给体数：
  2
• 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：

  2-(7-甲氧基吲哚-1H-3-基)乙酸 在 盐酸 、 吡啶硼烷 、 乙醇 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.5h， 生成 2-(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-7-methoxy-1H-indol-3-yl)acetic acid
  参考文献：
  名称：

  INDOLEACETIC ACID DERIVATIVE AND PREPARATION METHOD AND PHARMACEUTICAL USE THEREOF

  摘要：

  本发明涉及一种吲哚乙酸衍生物及其制备方法和药用。具体地，本发明涉及一种通式(I)所示的化合物，其制备方法，包含该化合物的药物组合物，以及其作为咳嗽镇咳剂用于治疗咳嗽等疾病的用途。通式(I)中的每个取代基的定义与说明书中的定义相同。

  公开号：

  US20200095271A1
• 作为产物：
  描述：

  7-methoxyindole-3-glyoxyl chloride 在 palladium on activated charcoal 氢氧化钾 、 sodium hypophosphite 、 三乙胺 、 异丁酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 52.0h， 生成 2-(7-甲氧基吲哚-1H-3-基)乙酸
  参考文献：
  名称：

  Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana

  摘要：

  Three metabolites of indole-3-acetic acid (IAA), N-(6-hydroxyindol-3-ylacetyl)-phenylalanine (6-OH-IAA-Phe), N-(6-hydroxyindol-3-ylacetyl)-valine (6-OH-IAA-Val), and 1-O-(2-oxoindol-3-ylacetyl)-beta-D-glucopyranose (OxIAA-Glc), were found by a liquid chromatography-elect ro spray ionization-tandem mass spectrometry (LC-ESI-MS/MS)-based search for oxidative IAA metabolites during the vegetative growth of Arabidopsis. Their structures were confirmed by making a comparison of chromatographic characteristics and mass spectra between naturally occurring compounds and synthetic standards. An incorporation study using deuterium-labeled compounds showed that 6-OH-IAA-Phe and 6-OH-IAA-Val were biosynthesized from IAA-Phe and IAA-Val, respectively, which strongly suggested the formation of these;imino acid conjugates of IAA in plants. Both 6-OH-IAA-Phe and 6-OH-IAA-Val were inactive as auxins, as indicated by no significant root growth inhibition in Arabidopsis. Quantitative analysis demonstrated that OxIAA-Glc was present in the largest amount among the metabolites of IAA in Arabidopsis, suggesting that the conversion into OxIAA-Glc represents the main metabolic process regarding IAA in Arabidopsis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.04.030

文献信息

• [EN] CDK2 INHIBITORS AND METHODS OF USING THE SAME<br/>[FR] INHIBITEURS DE CDK2 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CEDILLA THERAPEUTICS INC

  公开号：WO2022272106A1

  公开（公告）日：2022-12-29

  The present disclosure relates generally to Cyclin-dependent kinase 2 (CDK2) inhibiting chemical compounds and uses thereof in the inhibition of the activity of CDK2. The disclosure also provides pharmaceutically acceptable compositions comprising compounds disclosed herein and methods of using said compounds and compositions in the treatment of various disorders related to CDK2 activity.

  本公开涉及抑制Cyclin-dependent kinase 2（CDK2）活性的化学化合物及其在抑制CDK2活性方面的用途。本公开还提供了包含所披露化合物的药学上可接受的组合物以及使用上述化合物和组合物在治疗与CDK2活性相关的各种疾病方面的方法。
• Indole-3-Acetamido-Polyamines as Antimicrobial Agents and Antibiotic Adjuvants
  作者：Kenneth Sue、Melissa M. Cadelis、Evangelene S. Gill、Florent Rouvier、Marie-Lise Bourguet-Kondracki、Jean Michel Brunel、Brent R. Copp

  DOI：10.3390/biom13081226

  日期：——

  The widespread incidence of antimicrobial resistance necessitates the discovery of new classes of antimicrobials as well as adjuvant molecules that can restore the action of ineffective antibiotics. Herein, we report the synthesis of a new class of indole-3-acetamido-polyamine conjugates that were evaluated for antimicrobial activities against a panel of bacteria and two fungi, and for the ability to enhance the action of doxycycline against Pseudomonas aeruginosa and erythromycin against Escherichia coli. Compounds 14b, 15b, 17c, 18a, 18b, 18d, 19b, 19e, 20c and 20d exhibited strong growth inhibition of methicillin-resistant Staphylococcus aureus (MRSA) and Cryptococcus neoformans, with minimum inhibitory concentrations (MIC) typically less than 0.2 µM. Four analogues, including a 5-bromo 15c and three 5-methoxyls 16d–f, also exhibited intrinsic activity towards E. coli. Antibiotic kill curve analysis of 15c identified it to be a bactericide. While only one derivative was found to (weakly) enhance the action of erythromycin against E. coli, three examples, including 15c, were found to be strong enhancers of the antibiotic action of doxycycline against P. aeruginosa. Collectively, these results highlight the promising potential of α,ω-disubstituted indole-3-acetamido polyamine conjugates as antimicrobials and antibiotic adjuvants.

  由于抗菌药耐药性的广泛存在，因此有必要发现新的抗菌药类别以及能够恢复无效抗生素作用的辅助分子。在此，我们报告了一类新的吲哚-3-乙酰胺基多胺共轭物的合成，并评估了它们对一系列细菌和两种真菌的抗菌活性，以及增强强力霉素对绿脓杆菌和红霉素对大肠杆菌作用的能力。化合物 14b、15b、17c、18a、18b、18d、19b、19e、20c 和 20d 对耐甲氧西林金黄色葡萄球菌（MRSA）和新型隐球菌具有很强的生长抑制作用，最低抑制浓度（MIC）通常低于 0.2 µM。四种类似物，包括一种 5-溴 15c 和三种 5-甲氧基 16d-f，对大肠杆菌也具有内在活性。15c 的抗生素杀灭曲线分析表明它是一种杀菌剂。虽然只有一种衍生物被发现能（弱）增强红霉素对大肠杆菌的作用，但包括 15c 在内的三种衍生物被发现能强烈增强强力霉素对绿脓杆菌的抗生素作用。总之，这些结果凸显了α,ω-二取代吲哚-3-乙酰胺基多胺共轭物作为抗菌剂和抗生素佐剂的巨大潜力。
• Applying deep learning to iterative screening of medium-sized molecules for protein–protein interaction-targeted drug discovery
  作者：Yugo Shimizu、Tomoki Yonezawa、Yu Bao、Junichi Sakamoto、Mariko Yokogawa、Toshio Furuya、Masanori Osawa、Kazuyoshi Ikeda

  DOI：10.1039/d3cc01283b

  日期：——

  Updating predicting models could greatly improve the hit rate of virtual screening for identifying Keap1/Nrf2 protein–protein interaction inhibitors.

  更新预测模型可以大大提高虚拟筛选的命中率，从而确定 Keap1/Nrf2 蛋白-蛋白相互作用抑制剂。
• Indoleacetic acid derivative and preparation method and pharmaceutical use thereof
  申请人：Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences

  公开号：US11008360B2

  公开（公告）日：2021-05-18

  The present invention relates to an indoleacetic acid derivative and a preparation method and pharmaceutical use thereof. In particular, the present invention relates to a compound shown in general formula (I), a preparation method thereof, a pharmaceutical composition comprising the same, and a use thereof as a cough suppressant in treating a disease such as a cough. The definition of each substituent in the general formula (I) is the same as the definition in the specification.

  本发明涉及一种吲哚乙酸衍生物及其制备方法和药物用途。特别是，本发明涉及通式（I）所示的一种化合物、其制备方法、由其组成的药物组合物，以及其在治疗咳嗽等疾病中作为镇咳剂的用途。通式（I）中各取代基的定义与说明书中的定义相同。
• THE SYNTHESIS OF CERTAIN SUBSTITUTED INDOLEACETIC ACIDS¹
  作者：STEPHEN P. FINDLAY、GREGG DOUGHERTY

  DOI：10.1021/jo01162a014

  日期：1948.7