4-甲氧基-1H-吲哚-3-甲酸 | 203937-50-2

• 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: 4-甲氧基-1H-吲哚-3-甲酸
• 中文别名: 4-甲氧基吲哚-3-甲酸
• 英文名称: 4-methoxy-1H-indole-3-carboxylic acid
• CAS: 203937-50-2
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: CWWWWJZMLMUDIM-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±25.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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
• WGK Germany：
  3

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methoxyindole-3-carboxylic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Methoxyindole-3-carboxylic acid
CAS number: 203937-50-2

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H9NO3
Molecular weight: 191.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-甲氧基-1H-吲哚-3-甲酸 在 三溴化硼 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 2-[1-(4-fluorobenzyl)-4-hydroxy-1H-indole-3-carboxamido]acetic acid
  参考文献：
  名称：

  Fragment hopping approach directed at design of HIV IN-LEDGF/p75 interaction inhibitors

  摘要：

  We recently identified a series of indole derivatives as active inhibitors of IN-LEDGF/p75 interaction through structure-based pharmacophore models generated from the crystal structure of dimeric catalytic core domain (CCD) of HIV-1 IN in complex with the LEDGF integrase binding domain (IBD). In this paper we used the fragment hopping approach to design small molecules able to prevent the IN-LEDGF/p75 interaction. By means of the proposed approach, we designed novel non-peptidyl compounds that mimic the biological function of some IBD residues and in particular the LEDGF hot spot residues Ile365 and Asp366. The biological results confirmed the importance of several structural requirements for the inhibitory effects of this class of compounds.

  DOI：

  10.3109/14756366.2012.703184
• 作为产物：
  描述：

  4-甲氧基吲哚-3-甲醛 在 sodium dihydrogenphosphate dihydrate 作用下， 以 (E)-2-Methoxy-2-buten 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 以91%的产率得到4-甲氧基-1H-吲哚-3-甲酸
  参考文献：
  名称：

  Interaction of cruciferous phytoanticipins with plant fungal pathogens: Indole glucosinolates are not metabolized but the corresponding desulfo-derivatives and nitriles are

  摘要：

  Glucosinolates represent a large group of plant natural products long known for diverse and fascinating physiological functions and activities. Despite the relevance and huge interest on the roles of indole glucosinolates in plant defense, little is known about their direct interaction with microbial plant pathogens. Toward this end, the metabolism of indolyl glucosinolates, their corresponding desulfo-derivatives, and derived metabolites, by three fungal species pathogenic on crucifers was investigated. While glucobrassicin, 1-methoxyglucobrassicin, 4-methoxyglucobrassicin were not metabolized by the pathogenic fungi Alternaria brassicicola, Rhizoctonia solani and Sclerotinia sclerotiorum, the corresponding desulfo-derivatives were metabolized to indolyl-3-acetonitrile, caulilexin C (1-methoxyindolyl-3-acetonitrile) and arvelexin (4-methoxyindolyl-3-acetonitrile) by R. solani and S. sclerotiorum, but not by A. brassicicola. That is, desulfo-glucosinolates were metabolized by two non-host-selective pathogens, but not by a host-selective. Indolyl-3-acetonitrile, caulilexin C and arvelexin were metabolized to the corresponding indole-3-carboxylic acids. Indolyl-3-acetonitriles displayed higher inhibitory activity than indole desulfo-glucosinolates. Indolyl-3-methanol displayed antifungal activity and was metabolized by A. brassicicola and R. solani to the less antifungal compounds indole-3-carboxaldehyde and indole-3-carboxylic acid. Diindolyl-3-methane was strongly antifungal and stable in fungal cultures, but ascorbigen was not stable in solution and displayed low antifungal activity; neither compound appeared to be metabolized by any of the three fungal species. The cell-free extracts of mycelia of A. brassicicola displayed low myrosinase activity using glucobrassicin as substrate, but myrosinase activity was not detectable in mycelia of either R. solani or S. sclerotiorum. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.08.018

文献信息

• QUINUCLIDINES FOR MODULATING ALPHA 7 ACTIVITY
  申请人：CoMentis, Inc.

  公开号：US20160009706A1

  公开（公告）日：2016-01-14

  Provided are substituted quinuclidine compounds, pharmaceutical compositions comprising such compounds, and methods of modulating α7 nicotinic acetylcholine receptors and treating neurological disorders using such compounds.

  提供了替代性的喹诺啡啶化合物，包括这些化合物的药物组合物，以及使用这些化合物调节α7烟碱乙酰胆碱受体和治疗神经系统疾病的方法。
• [EN] INHIBITORS OF HEXOKINASE AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS D'HEXOKINASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：VTV THERAPEUTICS LLC

  公开号：WO2018009539A1

  公开（公告）日：2018-01-11

  Provided herein are substituted substituted heterocycles useful as inhibitors of the HKII enzyme. The invention further provides pharmaceutical compositions of the compounds of the invention. The invention further provides medical uses of substituted heterocycles, for example, as antitumor agents.

  本文提供了作为HKII酶抑制剂的替代杂环化合物。本发明还提供了本发明化合物的药物组合物。此外，本发明还提供了替代杂环化合物的医药用途，例如作为抗肿瘤剂。
• Discovery of indolylpiperazinylpyrimidines with dual-target profiles at adenosine A2A and dopamine D2 receptors for Parkinson's disease treatment
  作者：Yi-Ming Shao、Xiaohua Ma、Priyankar Paira、Aaron Tan、Deron Raymond Herr、Kah Leong Lim、Chee Hoe Ng、Gopalakrishnan Venkatesan、Karl-Norbert Klotz、Stephanie Federico、Giampiero Spalluto、Siew Lee Cheong、Yu Zong Chen、Giorgia Pastorin

  DOI：10.1371/journal.pone.0188212

  日期：——

  dyskinesia, motor fluctuations and psychosis. Non-dopaminergic receptors, such as human A2A adenosine receptors, have emerged as important therapeutic targets in potentiating therapeutic effects and reducing the unwanted side effects. In this study, new chemical entities targeting both human A2A adenosine receptor and dopamine D2 receptor were designed and evaluated. Two computational methods, namely support

  帕金森氏病（PD）是一种神经退行性疾病，其特征在于人脑黑质中多巴胺能神经元的进行性丧失，导致多巴胺产生的消耗。多巴胺替代疗法仍然是减轻PD症状的主要手段。但是，当前药物治疗的潜在益处大多受到不良副作用的限制，例如药物引起的运动障碍，运动波动和精神病。非多巴胺能受体，例如人A2A腺苷受体，已成为增强治疗效果和减少不良副作用的重要治疗靶标。在这项研究中，设计并评估了针对人A2A腺苷受体和多巴胺D2受体的新化学实体。两种计算方法 集成支持向量机（SVM）模型和基于Tanimoto基于相似度的聚类分析，以鉴定包含吲哚-哌嗪-嘧啶（IPP）支架的化合物。随后的合成和测试产生了化合物5和6，它们在放射性配体竞争测定中用作人A2A腺苷受体结合剂（Ki = 8.7-11.2μM），在人工细胞膜测定中用作人多巴胺D2受体结合剂（EC50 = 22.5） -40.2μM）。此外，在PD的果蝇模型中，化合物5显
• Access to 2-Arylindoles via Decarboxylative C−C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts
  作者：Velladurai Arun、Meenakshi Pilania、Dalip Kumar

  DOI：10.1002/asia.201601290

  日期：2016.12.6

  accessible heteroaromatic carboxylic acids and diaryliodonium salts were successfully employed to construct valuable 2‐arylindoles and heteroaryl carboxylates in a regioselective fashion. C2‐arylated indoles were produced using a Pd‐catalyzed decarboxylative strategy in water without any base, oxidant, or ligand. Heteroaryl carboxylates were prepared under metal and base‐free conditions. This protocol was

  容易获得的杂芳族羧酸和二芳基碘鎓盐已成功用于以区域选择性的方式构建有价值的2-芳基吲哚和杂芳基羧酸盐。C2芳基吲哚是在水中没有任何碱，氧化剂或配体的情况下使用Pd催化的脱羧策略生产的。杂芳基羧酸盐是在无金属和无碱条件下制备的。该方案已成功用于合成细胞周期蛋白依赖性激酶（CDK）抑制剂Paullone。
• Divergent reactivity of an indole glucosinolate yields Lossen or Neber rearrangement products: the phytoalexin rapalexin A or a unique β-<scp>d</scp>-glucopyranose fused heterocycle
  作者：M. S. C. Pedras、Q. H. To、G. Schatte

  DOI：10.1039/c5cc09822j

  日期：——

  Transformation of 1-t-Boc-4-methoxyindole-3-glucosinolate in acidic conditions yielded the potent phytoalexin rapalexin A, providing its first biomimetic synthesis via Lossen type rearrangement, while the novel 1-thioimidocarbonyl-[small beta]-D-glucopyranose heterocyclic system was obtained in...

  在酸性条件下转化1-t-Boc-4-甲氧基吲哚-3-葡糖基磺酸盐产生有效的植物抗毒素rapalexin A，通过Lossen类型重排提供其首次仿生合成，而新型1-硫代亚氨基羰基-[小β] -D-吡喃葡萄糖杂环系统是在...