(5-氟-2-甲基-1H-吲哚-3-基)乙酸 | 71987-67-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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-氟-2-甲基-1H-吲哚-3-基)乙酸
• 英文名称: 2-(5-fluoro-2-methyl-1H-indol-3-yl)acetic acid
• 英文别名: (5-fluoro-2-methyl-1H-indol-3-yl)acetic acid
• CAS: 71987-67-2
• 化学式: C₁₁H₁₀FNO₂
• mdl: MFCD02664389
• 分子量: 207.204
• InChiKey: VJZAMNBVIWOUJR-UHFFFAOYSA-N

物化性质

• 熔点：
  179-182 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  421.1±40.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (5-Fluoro-2-methyl-1H-indol-3-yl)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-Fluoro-2-methyl-1H-indol-3-yl)acetic acid
CAS number: 71987-67-2

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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: C11H10FNO2
Molecular weight: 207.2

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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, hydrogen fluoride.

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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-氟-2-甲基-1H-吲哚-3-基)乙酸 在 sodium hydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  通过可见光诱导的自由基级联反应 合成功能化吡咯并吲哚啉：（±）-氟雌醇B †的快速合成

  摘要：

  报道了通过自由基级联反应的可见光诱导的功能化吡咯并吲哚啉合成的发展。该反应显示出较宽的底物范围并突出了反应条件的温和性质。吲哚芳族环和N-中心的一系列取代均被很好地耐受，包括游离的烯丙醇。依靠该策略，实现了（±）-氟雌醇B的快速合成。

  DOI：

  10.1039/c8cc03575j
• 作为产物：
  描述：

  乙酰丙酸乙酯 在 sodium hydroxide 、 硫酸 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (5-氟-2-甲基-1H-吲哚-3-基)乙酸
  参考文献：
  名称：

  新的N-（吡啶-4-基）-（吲哚-3-基）乙酰胺和丙酰胺作为抗过敏剂。

  摘要：

  为了寻找新的抗过敏化合物，已经制备了一系列新的N-（吡啶-4-基）-（吲哚-3-基）烷基酰胺44-84。通过在Fischer条件下进行吲哚化来合成所需的（2-甲基吲哚-3-基）乙酸乙酯1-4。Japp-Klingemann方法，然后进行2-脱羧，得到（吲哚-3-基）链烷酸乙酯17-25。通过使相应的酸或其N-芳基（甲基）衍生物与2-氯-1-甲基吡啶碘化物促进的4-氨基吡啶缩合而成功进行了酰胺化反应。通过改变吲哚取代基（R1，R2，R）和烷链长度（n = 1、2、3）来改善标题系列的抗过敏效力的努力导致选择N-（吡啶-4 41种化合物中的45-基）-[1-（4-氟苄基）吲哚-3-基]乙酰胺45。使用豚鼠腹膜肥大细胞，在卵白蛋白诱导的组胺释放测定中，该酰胺的效价比阿司咪唑高406倍，IC50 = 0.016 microM。在Th-2细胞的IL-4产生测试中，其抑制活性与参考组胺拮抗剂的抑制活性相同（IC50

  DOI：

  10.1021/jm981079+
• 作为试剂：
  描述：

  methyl 2-(5-fluoro-2-methyl-1H-indol-3-yl)acetate 、 methyl 2-(5-(trifluoromethyl)-1H-indol-3-yl)acetate 在 (5-氟-2-甲基-1H-吲哚-3-基)乙酸 作用下， 生成 (5-氟-2-甲基-1H-吲哚-3-基)乙酸
  参考文献：
  名称：

  COMPOUNDS FOR THE TREATMENT OF HIV

  摘要：

  本发明提供了以下式子（I）的化合物或其盐，如本文所述。本发明还提供了包括式子（I）化合物的制药组合物，制备式子（I）化合物的方法，用于制备式子I化合物的中间体以及治疗逆转录病毒感染的治疗方法，包括由HIV病毒引起的感染。

  公开号：

  US20140142085A1

文献信息

• [EN] COMPOUNDS FOR USE IN THE TREATMENT OF KINETOPLASTID INFECTION<br/>[FR] COMPOSÉS UTILISÉS POUR TRAITER UNE INFECTION CINÉTOPLASTIDE
  申请人：IRBM SCIENCE PARK S P A

  公开号：WO2018115275A1

  公开（公告）日：2018-06-28

  The present invention relates to a class of novel heterocyclic compounds, to pharmaceutical compositions comprising the compounds and their use in the treatment of kinetoplastid infections.

  本发明涉及一类新颖的杂环化合物，以及包含这些化合物的药物组合物及其在治疗运动毛虫感染中的用途。
• Synthesis, Characterization and Antibacterial Evaluation of some New 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines as Potential Antibacterial Agents
  作者：Kooi-Mow Sim、Kah-Cheng Teo

  DOI：10.2174/1570180814666170922165933

  日期：2018.5.30

  -3-yl)methyl]- 1,2,4-triazoles with a series of phenacyl bromides produced the corresponding 1,2,4-triazolo[3,4- b][1,3,4]thiadiazines. The structures of 1,2,4-triazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines were elucidated by IR, NMR and mass spectral data and were evaluated for their antibacterial activity using 96-well microbroth dilution assay. Results: In the current study, two new 4-a

  背景：吲哚衍生物和1,2,4-三唑并[3,4-b] [1,3,4]噻二嗪是药物化学中重要的杂环化合物。它们显示出广泛的生物学活性，例如抗癌，抗微生物，抗氧化剂和抗炎活性。 目的：本研究的目的是合成4-氨基-5-巯基-3-[（5-取代的2-甲基-1H-吲哚-3-基）甲基] -1,2,4-三唑和1 ，2,4-三唑并[3,4-b] [1,3,4]噻二嗪并入吲哚骨架并评估其抗菌活性。 方法：由5-取代基的融合反应合成了4-氨基-5-巯基-3-[（5-取代-2-甲基-1H-吲哚-3-基）甲基] -1,2,4-三唑。 -2-甲基吲哚-3-乙酸与硫代碳酰肼。4-氨基-5-巯基-3-[（5-取代-2-甲基-1H-吲哚-3-基）甲基] -1,2,4-三唑与一系列苯甲酰溴的反应产生了相应的1,2,4-三唑并[3,4-b] [1,3,4]噻二嗪。红外，核磁共振和质谱数据阐明了1,2,4-三唑和1,2,4-三唑并[3
• [DE] 4-AMINOMETHYL-1-ARYL-CYCLOHEXYLAMIN-DERIVATE<br/>[EN] 4-AMINOMETHYL-1-ARYL-CYCLOHEXYLAMINE DERIVATIVES<br/>[FR] DERIVES DE 4-AMINOMETHYL-1-ARYL-CYCLOHEXYLAMINE
  申请人：GRUENENTHAL GMBH

  公开号：WO2004043899A1

  公开（公告）日：2004-05-27

  Die vorliegende Erfindung betrifft 4-Aminomethyl-1-Ary.-Cyclohexylamin-Derivate, verfahren zu deren Herstellung, Arzneimittel enthaltend diese Verbindung und die Verwendung von 4-Aminomethyl-1-Aryl-Cyclohexylamin-Derivaten zur Herstellung von Arzneimitteln.

  这项发明涉及4-氨甲基-1-芳基-环己胺衍生物，其制备方法，含有该化合物的药物，以及利用4-氨甲基-1-芳基-环己胺衍生物制备药物的用途。
• Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy
  作者：Sharon Rossiter、Lisa K Folkes、Peter Wardman

  DOI：10.1016/s0960-894x(02)00505-x

  日期：2002.9

  Substituted indole-3-acetic acid (IAA) derivatives, plant auxins with potential for use as prodrugs in enzyme-prodrug directed cancer therapies, were oxidised with horseradish peroxidase (HRP) and toxicity against V79 Chinese hamster lung fibroblasts was determined. Rate constants for oxidation by HRP compound I were also measured. Halogenated IAAs were found to be the most cytotoxic, with typical

  用辣根过氧化物酶（HRP）氧化取代的吲哚-3-乙酸（IAA）衍生物，可能用作酶前药导向的癌症治疗前药的植物生长素，并确定其对V79中国仓鼠肺成纤维细胞的毒性。还测量了由HRP化合物I氧化的速率常数。与100 microM前体药物和HRP孵育2h后，发现卤化的IAA具有最高的细胞毒性，典型的存活分数<10（-3）。
• [EN] NOVEL N-(2,3-DIHYDRO-1H-PYRROLO[2,3-B]JPYRIDIN-5-YL)-4- QUINAZOLINAMINE AND N-(2,3-DIHYDRO-1H-INDOL-5-YL)-4- QUINAZOLINAMINE DERIVATIVES AS PERK INHIBITORS<br/>[FR] DÉRIVÉS N-(2,3-DIHYDRO-1H-PYRROLO[2,3-B]PYRIDIN-5-YL)-4-QUINAZOLINAMINE ET N-(2,3-DIHYDRO-1H-INDOL-5-YL)-4-QUINAZOLINAMINE D'UN NOUVEAU TYPE EN TANT QU'INHIBITEURS DE PERK
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2014161808A1

  公开（公告）日：2014-10-09

  The present invention relates to N-(2,3-dihydro-1H-pyrrolo[2,3-b)]pyridin-5-yl)-4-quinazolinamine and N-(2.3-dihydro-1H-indol-5-yl)-4-quinazolinamine derivatives of Formula (I) wherein R1, R2, R3, R4, R5, R6 and A have the meaning defined in the claims. The compounds according to the present invention are useful as inhibitors of PERK. The invention further relates to processes for preparing such compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及Formula (I)中的N-(2,3-二氢-1H-吡咯[2,3-b)]吡啶-5-基)-4-喹唑啉胺和N-(2.3-二氢-1H-吲哚-5-基)-4-喹唑啉胺衍生物，其中R1、R2、R3、R4、R5、R6和A的含义如索赔中所定义。根据本发明的化合物可用作PERK的抑制剂。本发明还涉及制备这些化合物的方法、包含上述化合物作为活性成分的药物组合物以及将上述化合物用作药物的用途。