7-甲氧基-1H-吲哚-3-甲酸 | 128717-77-1

• 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-3-甲酸
• 中文别名: 7-甲氧基吲哚-3-甲酸
• 英文名称: 7-methoxy-1H-indole-3-carboxylic acid
• 英文别名: 7-Methoxyindole-3-carboxylic acid
• CAS: 128717-77-1
• 化学式: C₁₀H₉NO₃
• mdl: MFCD05664009
• 分子量: 191.186
• InChiKey: MSALXMDIYCKASR-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
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 7-Methoxy-1h-indole-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: 7-Methoxy-1h-indole-3-carboxylic acid
CAS number: 128717-77-1

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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：

  7-甲氧基-1H-吲哚-3-甲酸 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-甲氧基-1H-吲哚-3-甲酰氯
  参考文献：
  名称：

  Weakly coordinating tert-amide assisted Rh(iii)-catalyzed C4-cyanation of indoles: application in photophysical studies

  摘要：

  本研究介绍了一种由铑(iii)催化的吲哚 C4 选择性氰化反应，该反应以工作台稳定、使用方便的亲电氰化剂 N-氰基-N-苯基对甲苯磺酰胺 (NCTS) 为偶联剂。

  DOI：

  10.1039/d3cc03075j
• 作为产物：
  描述：

  7-methoxy-3-[(trifluoromethyl)carbonyl]-1H-indole 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 7-甲氧基-1H-吲哚-3-甲酸
  参考文献：
  名称：

  [EN] 1-[(INDOL-3-YL)CARBONYL] PIPERAZINE DERIVATIVES
  [FR] DERIVES DE 1-[(INDOL-3-YL)CARBONYL] PIPERAZINE

  摘要：

  本发明涉及根据通式（I）的1-[(indol-3-yl)carbonyl]哌嗪衍生物，其中R代表独立选择的1-4个取代基，包括H，（C1-4）烷基（可选择用卤素取代），（C1-4）烷氧基（可选择用卤素取代），卤素，羟基，氨基，氰基和硝基；R1为（C5-8）环烷基或（C5-8）环烯基；R2为H，甲基或乙基；R3，R3'，R4'，R4'，R5，R5'和R6'独立地为氢或（C1-4）烷基，可选择用（C1-4）烷氧基，卤素或羟基取代；R6为氢或（C1-4）烷基，可选择用（C1-4）烷氧基，卤素或羟基取代；或R6与R7一起形成一个含有O和S等进一步杂原子的4-7元饱和杂环；R7与R6一起形成一个含有O和S等进一步杂原子的4-7元饱和杂环；或R7为H，（C1-4）烷基或（C3-5）环烷基，烷基基团可选择用羟基，卤素或（C1-4）烷氧基取代；或其药学上可接受的盐。该发明还涉及包含所述1-[(indol-3-yl)carbonyl]哌嗪衍生物的药物组合物，并且涉及在治疗疼痛方面使用这些衍生物，如围手术疼痛，慢性疼痛，神经病性疼痛，癌症疼痛以及与多发性硬化症相关的疼痛和痉挛。

  公开号：

  WO2004000832A1

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] 1-[(INDOL-3-YL)CARBONYL] PIPERAZINE DERIVATIVES<br/>[FR] DERIVES DE 1-[(INDOL-3-YL)CARBONYL] PIPERAZINE
  申请人：AKZO NOBEL NV

  公开号：WO2004000832A1

  公开（公告）日：2003-12-31

  The present invention relates to 1-[(indol-3-yl)carbonyl]piperazine derivative according to the general formula (I), wherein R represents 1-4 substituents independently selected from H, (C1-4)alkyl (optionally substituted with halogen), (C 1-4)alkyloxy (optionally substituted with halogen), halogen, OH, NH2, CN and NO2; R1 is (C5-8)cycloalkyl or (C5-8)cycloalkenyl; R2 is H, methyl or ethyl; R3, R3', R4' R4', R5, R5' and R6' are independently hydrogen or (C1-4)alkyl, optionally substituted with (C1-4)alkyloxy, halogen or OH; R6 is hydrogen or (C1-4)alkyl, optionally substituted with (C1-4)alkyloxy, halogen or OH; or R6 forms together with R7 a 4-7 membered saturated heterocyclic ring, optionally containing a further heteroatom selected from O and S; R7 forms together with R6 a 4-7 membered saturated heterocyclic ring, optionally containing a further heteroatom selected from O and S; or R7 is H, (C1-4)alkyl or (C3-5)cycloalkyl, the alkyl groups being optionally substituted with OH, halogen or (C1-4)alkyloxy; or a pharmaceutically acceptable salt thereof. The invention also relates to pharmaceutical compositions comprising said 1-[(indol-3-yl)carbonyl]piperazine derivatives, and to the use of these derivatives in the treatment of pain, such as peri-operative pain, chronic pain neuropathic pain, cancer pain, and pain and spasticity associated with multiple sclerosis.

  本发明涉及根据通式（I）的1-[(indol-3-yl)carbonyl]哌嗪衍生物，其中R代表独立选择的1-4个取代基，包括H，（C1-4）烷基（可选择用卤素取代），（C1-4）烷氧基（可选择用卤素取代），卤素，羟基，氨基，氰基和硝基；R1为（C5-8）环烷基或（C5-8）环烯基；R2为H，甲基或乙基；R3，R3'，R4'，R4'，R5，R5'和R6'独立地为氢或（C1-4）烷基，可选择用（C1-4）烷氧基，卤素或羟基取代；R6为氢或（C1-4）烷基，可选择用（C1-4）烷氧基，卤素或羟基取代；或R6与R7一起形成一个含有O和S等进一步杂原子的4-7元饱和杂环；R7与R6一起形成一个含有O和S等进一步杂原子的4-7元饱和杂环；或R7为H，（C1-4）烷基或（C3-5）环烷基，烷基基团可选择用羟基，卤素或（C1-4）烷氧基取代；或其药学上可接受的盐。该发明还涉及包含所述1-[(indol-3-yl)carbonyl]哌嗪衍生物的药物组合物，并且涉及在治疗疼痛方面使用这些衍生物，如围手术疼痛，慢性疼痛，神经病性疼痛，癌症疼痛以及与多发性硬化症相关的疼痛和痉挛。
• Escaping from Flatland: Antimalarial Activity of sp³-Rich Bridged Pyrrolidine Derivatives
  作者：Brian Cox、James Duffy、Victor Zdorichenko、Corentin Bellanger、Jessica Hurcum、Benoît Laleu、Kevin I. Booker-Milburn、Luke D. Elliott、Michael Robertson-Ralph、Christopher J. Swain、Stephen J. Bishop、Irene Hallyburton、Mark Anderson

  DOI：10.1021/acsmedchemlett.0c00486

  日期：2020.12.10

  We utilized synthetic photochemistry to generate novel sp3-rich scaffolds and report the design, synthesis, and biological testing of a diverse series of amides based on the 1-(amino-methyl)-2-benzyl-2-aza-bicyclo[2.1.1]hexane scaffold. Preliminary antimalarial screening of the library provided promising compounds with activity in the 1–5 μM range with an enhanced hit rate. Further evaluation (solubility

  我们利用合成光化学生成了新型富含sp 3 的支架，并报告了基于 1-（氨基-甲基）-2-苄基-2-氮杂-双环 [2.1 .1]己烷支架。该文库的初步抗疟筛选提供了有希望的化合物，其活性范围为 1–5 μM，并具有更高的命中率。所选化合物 ( 9 ) 的进一步评估（溶解度、药物代谢和药代动力学 (DMPK) 和毒性）表明，该系列代表了进一步优化的绝佳机会，该框架为添加独特的矢量定位的额外功能提供了多种机会。
• [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