6-甲基-3-吲哚甲酸 | 209920-43-4

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 6-甲基-3-吲哚甲酸
• 中文别名: 6-甲基吲哚-3-甲酸；6-甲基-1H-吲哚-3-羧酸
• 英文名称: 6-methyl-1H-indole-3-carboxylic acid
• CAS: 209920-43-4
• 化学式: C₁₀H₉NO₂
• mdl: MFCD06203633
• 分子量: 175.187
• InChiKey: PHHZCIOPSFQASN-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C (decomp)
• 沸点：
  411.5±25.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

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: 6-Methyl-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: 6-Methyl-1H-indole-3-carboxylic acid
CAS number: 209920-43-4

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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: C10H9NO2
Molecular weight: 175.2

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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：

  6-甲基-3-吲哚甲酸 生成 6-甲基吲哚
  参考文献：
  名称：

  Sues; Moeller, Justus Liebigs Annalen der Chemie, 1955, vol. 593, p. 91,109

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基吲哚 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 三氯氧磷 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 6-甲基-3-吲哚甲酸
  参考文献：
  名称：

  鉴定 5-[5-氰基-1-(吡啶-2-基甲基)-1H-吲哚-3-甲酰氨基]噻唑-4-羧酸作为尿酸转运蛋白 1 和黄嘌呤氧化酶的有前途的双重抑制剂

  摘要：

  曲尼司特与别嘌呤醇联合作为尿酸转运蛋白1（URAT1）抑制剂用于治疗高尿酸血症，但其与URAT1抑制活性的构效关系鲜有研究。在本文中，在曲尼司特和优先支架吲哚的基础上，使用支架跳跃策略设计和合成了类似物。然后，使用 HEK293-URAT1 过表达细胞的 C-尿酸摄取测定来评估 URAT1 活性。与曲尼司特（10 μM 时抑制率为 44.9%）相比，大多数化合物对 URAT1 表现出明显的抑制作用，10 μM 时抑制率为 40.0% 至 81.0%。令人惊讶的是，随着在吲哚环5位引入氰基，化合物和 - 发挥了黄嘌呤氧化酶（XO）抑制活性。特别是，化合物对 URAT1（10 μM 时为 48.0%）和 XO（IC = 1.01 μM）具有效力。分子模拟分析表明该化合物的基本结构与URAT1、XO具有亲和力。此外，在测试期间，口服剂量为 10 mg/kg 的化合物在氧酸钾诱导的高尿酸血症大鼠模

  DOI：

  10.1016/j.ejmech.2023.115532

文献信息

• Copper-Mediated Cascade C–H/N–H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids
  作者：Ting-Yu Zhang、Chang Liu、Chao Chen、Jian-Xin Liu、Heng-Ye Xiang、Wei Jiang、Tong-Mei Ding、Shu-Yu Zhang

  DOI：10.1021/acs.orglett.7b03580

  日期：2018.1.5

  An efficient and environmentally benign Cu-mediated method was developed for direct cascade C–H/N–H annulation to construct polyheterocyclic indoloquinoline scaffolds. This method highlights an emerging strategy for transforming inert C–H bonds into versatile functional groups in organic synthesis and provides a new versatile approach for the efficient synthesis of indolo[3,2-c] and [2,3-c]quinoline

  开发了一种高效且环境友好的铜介导的方法，用于直接级联C–H / N–H环化，以构建多杂环吲哚并喹啉支架。该方法突出了在有机合成中将惰性C–H键转变为通用官能团的新兴策略，并为有效合成吲哚[3,2- c ]和[2,3- c ]喹啉生物碱提供了新的通用方法。
• Monoacylglycerol Lipase Modulators
  申请人：Janssen Pharmaceutica NV

  公开号：US20200102303A1

  公开（公告）日：2020-04-02

  Fused compounds of Formula (I) and Formula (II), pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with MGL modulation, such as those associated with pain, psychiatric disorders, neurological disorders (including, but not limited to major depressive disorder, treatment resistant depression, anxious depression, bipolar disorder), cancers and eye conditions. Wherein R 1 , R 2 , R 2a , R 3 , R 3a , R 4 , and R 4a are defined herein.

  化合物的结构式（I）和结构式（II），含有它们的药物组合物，制备它们的方法，以及使用它们的方法，包括用于治疗与MGL调节相关的疾病状态、紊乱和病况的方法，例如与疼痛、精神障碍、神经障碍（包括但不限于重性抑郁障碍、治疗抵抗性抑郁症、焦虑性抑郁症、躁郁症）、癌症和眼部疾病相关的方法。 其中R1、R2、R2a、R3、R3a、R4和R4a在此处定义。
• [EN] TETRAHYDROBENZO-QUINOLINE SULFONAMIDES DERIVATIVE COMPOUNDS<br/>[FR] COMPOSÉS DÉRIVÉS DE TÉTRAHYDROBENZO-QUINOLÉINE SULFONAMIDES
  申请人：UCB BIOPHARMA SRL

  公开号：WO2021130262A1

  公开（公告）日：2021-07-01

  The present invention relates to tetrahydrobenzo-isoquinoline sulfonamides derivatives of formula (I), processes for preparing them, pharmaceutical compositions containing them and their use in treating disorders caused by IgE (such as allergic responses, non-allergic mast cell responses or certain autoimmune responses), and in particular disorders caused by the interaction of IgE with the FcεRI receptor.

  本发明涉及公式（I）的四氢苯并异喹啉磺胺衍生物，制备它们的方法，含有它们的药物组合物以及它们在治疗由IgE引起的疾病（如过敏反应、非过敏肥大细胞反应或某些自身免疫反应）中的用途，特别是由IgE与FcεRI受体相互作用引起的疾病。
• Gold(III)-Catalyzed Decarboxylative C3-Benzylation of Indole-3-carboxylic Acids with Benzylic Alcohols in Water
  作者：Hidemasa Hikawa、Fumiya Kotaki、Shoko Kikkawa、Isao Azumaya

  DOI：10.1021/acs.joc.8b02947

  日期：2019.2.15

  the indole ring in the transition state. Furthermore, comparison of initial rates in H2O and in D2O reveals an observed kinetic solvent isotope effect (KSIE = 2.7). This simple protocol, which affords the desired products with CO2 and water as the coproducts, can be achieved under mild conditions without the need for base or other additives in water.

  已经开发了金（III）催化的吲哚-3-羧酸与苯甲醇的脱羧偶联反应的策略。这种级联反应被设计为3-苄基吲哚的简单有效的合成途径，产率中等至优异（50-93％）。Hammett对原脱羧的研究给出了一个负ρ值，表明在过渡态吲哚环上会积累正电荷。此外，比较H 2 O和D 2 O中的初始速率可发现观察到的动力学溶剂同位素效应（KSIE = 2.7）。这个简单的协议，提供所需的产品与CO 2 和水作为副产物，可以在温和的条件下获得，而无需在水中添加碱或其他添加剂。
• 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。