5-甲基吲哚-3-乙酸 | 1912-47-6

• 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: 5-甲基吲哚-3-乙酸
• 中文别名: 2-(5-甲基-1H-吲哚)-3-乙酸
• 英文名称: 5-methylindole-3-acetic acid
• 英文别名: 2-(5-methyl-1H-indol-3-yl)acetic acid
• CAS: 1912-47-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: VYFDKXJAORBSAW-UHFFFAOYSA-N

物化性质

• 熔点：
  151 °C
• 沸点：
  420.8±30.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Methylindole-3-acetic 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: 5-Methylindole-3-acetic acid
CAS number: 1912-47-6

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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: C11H11NO2
Molecular weight: 189.2

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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：

  5-甲基吲哚-3-乙酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 2.5h， 生成 benzyl 3-(3-acetoxy-2-oxopropyl)-5-methyl-1H-indole-1-carboxylate
  参考文献：
  名称：

  2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic Acid (PSI-697):  Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists

  摘要：

  P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.

  DOI：

  10.1021/jm060631p
• 作为产物：
  描述：

  2-(5-methyl-1H-indol-3-yl)-2-oxoacetyl chloride 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 18.5h， 生成 5-甲基吲哚-3-乙酸
  参考文献：
  名称：

  合成吲哚-3-乙酸的简便方法

  摘要：

  从相应的吲哚开始，通过吲哚-3-乙醛酸合成吲哚-3-乙酸，然后与对甲苯磺酰肼形成，然后用硼氢化钠还原hydr。

  DOI：

  10.1016/s0040-4039(00)76815-8

文献信息

• Reactivity toward Thiols and Cytotoxicity of 3-Methylene-2-oxindoles, Cytotoxins from Indole-3-acetic Acids, on Activation by Peroxidases
  作者：Lisa K. Folkes、Sharon Rossiter、Peter Wardman

  DOI：10.1021/tx025521+

  日期：2002.6.1

  Oxidation of indole-3-acetic acid and its derivatives by peroxidases such as that from horseradish produces many products, including 3-methylene-2-oxindoles. These have long been associated with biological activity, but their reactivity has not been characterized. We have previously demonstrated the potential value of substituted indole acetic acids and horseradish peroxidase as the basis for targeted

  吲哚-3-乙酸及其衍生物被辣根等过氧化物酶氧化后，会产生许多产物，包括3-亚甲基-2-氧吲哚。长期以来，这些都与生物活性有关，但尚未对其反应性进行表征。以前我们已经证明了取代的吲哚乙酸和辣根过氧化物酶作为靶向癌症治疗的基础的潜在价值，因为当观察到高细胞毒性时，化合物被氧化之前具有低细胞毒性。前药和酶的结合会消耗细胞内的硫醇。在这项研究中，合成了在3位，4位，5位或6位被甲基，F或Cl取代的3-亚甲基-2-氧吲哚及其衍生物，它们对代表性的巯基亲核试剂（谷胱甘肽，半胱氨酸，和半胱氨酸肽）使用停止流动力学分光光度法测量。在25°C的pH 7.4下，速率常数在大约2 x 10（3）到2 x 10（4）M（-）（1）s（-）（1）的范围内，这意味着数十倍的寿命这些亚甲基羟吲哚在细胞环境中的传播时间为毫秒，扩散距离为几微米。不出所料，卤素取代降低了辣根过氧化物酶处理中亚甲基羟吲哚的生成速率。使用中国仓
• CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING
  申请人：Reiley Pharmaceuticals, Inc.

  公开号：US20150374858A1

  公开（公告）日：2015-12-31

  Conjugates derived from non-steroidal anti-inflammatory drugs (NSAIDs) and methods of use thereof are disclosed, useful for, inter alia, identifying and localizing the site of pathology and/or inflammation responsible for the sensation of pain in a patient; for identifying the sites of primary, secondary, benign, or malignant tumors; and for diagnosing infection or confirming or ruling out suspected infection. The NSAID-based conjugates contain an imaging moiety. The conjugates concentrate at sites of increased cyclooxygenase expression, thus revealing the sites of increased prostaglandin production, which is correlated with pain and inflammation, and correlated with tumor presence and/or location. Identifying areas of increased COX expressing can also aid in screening for infections.

  披露了来自非甾体抗炎药（NSAIDs）的衍生物及其使用方法，这对于识别和定位患者疼痛感觉的病理和/或炎症部位；识别原发、继发、良性或恶性肿瘤的部位；以及诊断感染或确认或排除疑似感染非常有用。基于NSAID的偶联物含有成像基团。这些偶联物在环氧化酶表达增加的部位富集，从而揭示了前列腺素产生增加的部位，这与疼痛和炎症有关，并与肿瘤存在和/或位置有关。识别COX表达增加的区域也有助于筛查感染。
• A Photoredox‐Induced Stereoselective Dearomative Radical (4+2)‐Cyclization/1,4‐Addition Cascade for the Synthesis of Highly Functionalized Hexahydro‐1 <i>H</i> ‐carbazoles
  作者：Dirk Alpers、Malte Gallhof、Julian Witt、Frank Hoffmann、Malte Brasholz

  DOI：10.1002/anie.201610974

  日期：2017.1.24

  synthesis of functionalized hexahydrocarbazoles was developed based on an unprecedented photoredox‐induced dearomative radical (4+2)‐cyclization/1,4‐addition cascade between 3‐(2‐iodoethyl)indoles and acceptor‐substituted alkenes. The title reaction simultaneously generates three C−C bonds and one C−H bond, along with three contiguous stereogenic centers. The hexahydro‐1H‐carbazole products are highly valuable

  基于前所未有的光氧化还原诱导的3–（2-碘乙基）吲哚与受体取代的烯烃之间的脱氧自由基（4 + 2）-环化/ 1,4-加成级联反应，开发了功能化六氢咔唑的立体选择性合成方法。标题反应同时生成三个C-C键和一个C-H键，以及三个连续的立体中心。六氢-1 H-咔唑产品是合成新型抗生素以及多环吲哚啉生物碱的非天然环同源物的极有价值的中间体。
• Design, synthesis, and biological evaluation of tetrahydroisoquinolines derivatives as novel, selective PDE4 inhibitors for antipsoriasis treatment
  作者：Rui Zhang、Heng Li、Xianglei Zhang、Jian Li、Haixia Su、Qiukai Lu、Guangyu Dong、Huixia Dou、Chen Fan、Zhanni Gu、Qianwen Mu、Wei Tang、Yechun Xu、Hong Liu

  DOI：10.1016/j.ejmech.2020.113004

  日期：2021.2

  series of novel PDE4 inhibitors with a tetrahydroisoquinoline scaffold through structure-based drug design, among which compound 1 showed moderate inhibition activity against PDE4. In this study, a series of novel tetrahydroisoquinoline derivatives were developed based on the crystal structure of PDE4D in complex with compound 1. Anti-inflammatory effects of these compounds were evaluated, and compound

  银屑病是一种慢性炎症性皮肤病，而长期使用传统疗法治疗该疾病受到严重不良影响的限制。迫切需要与新的治疗机制相关的新型小分子。已知磷酸二酯酶4（PDE4）通过水解细胞内环状单磷酸腺苷（cAMP）在调节炎症反应中起着核心作用，使PDE4成为治疗炎性疾病（如牛皮癣）的重要靶标。在我们之前的工作中，我们通过基于结构的药物设计鉴定了一系列具有四氢异喹啉骨架的新型PDE4抑制剂，其中化合物1表现出对PDE4的中等抑制活性。在这项研究中，基于与化合物1络合的PDE4D的晶体结构，开发了一系列新型的四氢异喹啉衍生物。评估了这些化合物的抗炎作用，具有高安全性，通透性和选择性的化合物36对PDE4D的酶促活性以及从LPS刺激的RAW 264.7和hPBMC中释放的TNF-α表现出显着的抑制作用。此外，一项体内研究表明，局部给药36与卡泊三醇相比，在改善银屑病样皮肤炎症的特征方面取得了更显着的疗效。总体而言，我们
• Copper-Mediated Decarboxylative Sulfonylation of Arylacetic Acids with Sodium Sulfinates
  作者：Yinrong Wu、Jiewen Chen、Lu Li、Kangmei Wen、Xingang Yao、Jianxin Pang、Ting Wu、Xiaodong Tang

  DOI：10.1021/acs.orglett.0c02516

  日期：2020.9.18

  Herein, we present a copper-mediated decarboxylative sulfonylation of arylacetic acids with sodium sulfinates that provides viable access to sulfone compounds. This protocol features readily available feedstocks, simple operations, high regioselectivities, and moderate to good yields. The newly obtained products could be converted to other useful compounds. Importantly, the products and their derivatives

  在这里，我们介绍了铜磺酸与亚磺酸钠介导的芳基丙烯酸的脱羧磺酰化，提供了通向砜类化合物的可行途径。该方案的特点是易于获得的原料，操作简单，区域选择性高以及中等至良好的收率。新获得的产物可以转化为其他有用的化合物。重要的是，产物和它们的衍生物在体外表现出有效的抗肿瘤活性，这通过MTT测定法进行了测试。