5-羟基-2-甲基吲哚 | 13314-85-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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: 5-羟基-2-甲基吲哚
• 中文别名: 2-甲基-1H-吲哚-5-醇
• 英文名称: 2-methyl-1H-indol-5-ol
• 英文别名: 5-hydroxy-2-methylindole；2-methyl-5-hydroxyindole
• CAS: 13314-85-7
• 化学式: C₉H₉NO
• mdl: MFCD00022714
• 分子量: 147.177
• InChiKey: MDWJZBVEVLTXDE-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132℃
• 沸点：
  344.8±22.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 危险品标志：
  C
• 危险类别码：
  R34,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933990090
• 安全说明：
  S26,S27,S28,S36/37/39,S45
• 危险品运输编号：
  UN 3265 8/PG 2
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Hydroxy-2-methylindole
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-Hydroxy-2-methylindole
CAS number: 13314-85-7

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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, under −20◦C.
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: C9H9NO
Molecular weight: 147.2

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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

制备方法与用途

5-羟基-2-甲基吲哚用作研究用化合物。

反应信息

• 作为反应物：
  描述：

  5-羟基-2-甲基吲哚 在 palladium 10% on activated carbon 、 ammonium acetate 、 甲酸铵 、 三乙酰氧基硼氢化钠 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-methoxy-2-methyltryptamine
  参考文献：
  名称：

  Arp2/3 复合物小分子抑制剂的结构表征和计算机辅助优化，Arp2/3 复合物是肌动蛋白细胞骨架的关键调节剂

  摘要：

  CK-666 ( 1 ) 是最近发现的肌动蛋白相关蛋白 2/3 (Arp2/3) 复合物的小分子抑制剂，这是一种关键的肌动蛋白细胞骨架调节剂，在细菌发病机制和癌细胞运动中发挥作用。虽然1是市售的，但与1结合的 Arp2/3 复合物的晶体结构尚未见报道，因此其作用机制尚不确定。此外，其相对较低的效力增加了其体内脱靶效应的可能性，使其在细胞生物学研究中的影响解释复杂化并妨碍其临床应用。在此我们报告了与 Arp2/3 复合物结合的1的晶体结构，这表明1在 Arp2 和 Arp3 亚基之间结合以稳定复合物的无活性构象。基于晶体结构，我们使用1的单取代导数的计算对接和自由能微扰计算来指导优化工作。对十种新合成化合物进行生化分析，鉴定出化合物2，其体外抑制活性比1增加了三倍。此外，我们的计算分析揭示了 Arp2 和 Arp3 亚基界面处的表面凹槽，可用于额外的基于结构的优化。

  DOI：

  10.1002/cmdc.201200104
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 5-羟基-2-甲基吲哚
  参考文献：
  名称：

  Nenitzescu, Buletinul Societatii de Chimie din Romania, vol. 11, p. 37

  摘要：

  DOI：

文献信息

• Structure–activity relationship of 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole analogues as 5-HT6 receptor agonists
  作者：Cecilia Mattsson、Peder Svensson、Henning Boettcher、Clas Sonesson

  DOI：10.1016/j.ejmech.2013.03.006

  日期：2013.5

  structure–activity relationship (SAR) of the 5-hydroxytryptamine type 6 (5-HT6) receptor agonist 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (EMD386088, 6), a series of 2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles were synthesized, and in vitro affinity to, and functional activity at 5-HT6 receptors was tested. We focused on substituents made at the indole N1-, 2- and 5-positions

  进一步研究5-羟基色胺6型（5-HT 6）受体激动剂5-氯-2-甲基-3-（1,2,3,6-四氢吡啶-4--4-基）-1 ħ -吲哚（EMD386088，6），一系列的2-甲基-3-（1,2,3,6-四氢吡啶-4-基）-1 ħ -indoles合成，并在体外亲和力，测试了5-HT 6受体的功能活性。我们专注于在吲哚N 1-，2-和5-位上制得的取代基，发现这些取代基不仅会影响5-HT 6上的亲和力受体和内在活性导致拮抗剂，部分激动剂和完全激动剂。为了使化合物表现出有效的5-HT 6受体激动剂特性，吲哚N 1应该未被取代，需要烷基如2-甲基，最后是吲哚5-位的卤素取代基（氟，氯或氯）。溴）是必不可少的要求。然而，在N 1位引入苯磺酰基使完全激动剂6变成5-HT 6受体拮抗剂（30）。2-甲基-3-（1,2,3,6-四氢吡啶-4--4-基）-1 H中的一些化合物还对-吲哚进行脱靶筛选，通常它们
• Synthesis and Evaluation of Indole-Based Chalcones as Inducers of Methuosis, a Novel Type of Nonapoptotic Cell Death
  作者：Michael W. Robinson、Jean H. Overmeyer、Ashley M. Young、Paul W. Erhardt、William A. Maltese

  DOI：10.1021/jm201006x

  日期：2012.3.8

  providing insights into the contributions of the two aryl ring systems and highlighting a potent derivative, 3-(5-methoxy, 2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (i.e., MOMIPP) that can induce methuosis at low micromolar concentrations. We have also generated biologically active azide derivatives that may be useful for future studies aimed at identifying the protein targets of MOMIPP

  Methuosis 是一种新的不依赖于半胱天冬酶的细胞死亡形式，其中来自巨松质体的液泡的大量积累最终导致细胞从基质上分离并破裂。我们最近描述了一种查尔酮类化合物，3-(2-methyl-1 H -indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one（即 MIPP），它可以诱导胶质母细胞瘤和其他类型的癌细胞中的甲基化。在此，我们描述了相关化合物定向库的合成和结构-活性关系，提供了对两个芳环系统贡献的见解，并突出了一种有效的衍生物，3-(5-甲氧基，2-甲基-1 H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one（即 MOMIPP），可在低微摩尔浓度下诱导甲基化。我们还生成了具有生物活性的叠氮化物衍生物，这些衍生物可能对未来旨在通过光亲和标记技术识别 MOMIPP 的蛋白质靶标的研究有用。MOMIPP 可有效降低替莫唑胺耐药
• FUSED HETEROCYCLIC DERIVATIVE AND USE THEREOF
  申请人：Sakai Nozomu

  公开号：US20090137595A1

  公开（公告）日：2009-05-28

  The present invention provides a fused heterocyclic derivative having a potent kinase inhibitory activity and use thereof. A compound represented by the formula (I): wherein each symbol is as defined in the specification, except a particular compound, or a salt thereof, and a pharmaceutical agent containing the compound or a prodrug thereof, which is a kinase (VEGFR, VEGFR2, PDGFR, Raf) inhibitor, an angiogenesis inhibitor, an agent for the prophylaxis or treatment of cancer, a cancer growth inhibitor or a cancer metastasis suppressor.

  本发明提供了一种具有强大激酶抑制活性的融合杂环衍生物及其用途。 一种由以下式（I）表示的化合物： 其中除了特定化合物或其盐外，每个符号如规范中定义，以及含有该化合物或其前药的药用剂，该化合物是激酶（VEGFR、VEGFR2、PDGFR、Raf）抑制剂，血管生成抑制剂，用于癌症的预防或治疗的药剂，癌症生长抑制剂或癌症转移抑制剂。
• Indolyl-urea derivatives of thienopyridines useful as antiangiogenic agents, and methods for their use
  申请人：——

  公开号：US20040019065A1

  公开（公告）日：2004-01-29

  The invention relates to compounds represented by the formula I 1 and to prodrugs thereof, pharmaceutically acceptable salts or solvates of said compounds or said prodrugs, wherein X, R 1 and R 11 are as defined herein. The invention also relates to pharmaceutical compositions containing the compounds of formula I and to methods of treating hyperproliferative disorders in a mammal by administering the compounds of formula I.

  这项发明涉及由公式I表示的化合物，以及这些化合物的前药、药学上可接受的盐或溶剂，其中X、R1和R11如本文所定义。该发明还涉及含有公式I化合物的药物组合物，以及通过给予公式I化合物来治疗哺乳动物的过度增殖性疾病的方法。
• [EN] BENZOXAZINES AS MODULATORS OF ION CHANNELS<br/>[FR] BENZOXAZINES COMME MODULATEURS DES CANAUX IONIQUES
  申请人：VERTEX PHARMA

  公开号：WO2013067248A1

  公开（公告）日：2013-05-10

  The invention relates to benzoxazines useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及可用作离子通道抑制剂的苯并噁嗪。本发明还提供了包含本发明化合物的药用可接受组合物，以及使用这些组合物治疗各种疾病的方法。