7-溴-1H-吲哚-2-甲酸乙酯 | 16732-69-7

• 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: 7-溴-1H-吲哚-2-甲酸乙酯
• 中文别名: 7-溴-2-吲哚羧酸乙酯
• 英文名称: ethyl 7-bromo-1H-indole-2-carboxylate
• 英文别名: ethyl 7-bromoindole-2-carboxylate；7-Brom-indol-2-carbonsaeure-ethylester
• CAS: 16732-69-7
• 化学式: C₁₁H₁₀BrNO₂
• 分子量: 268.11
• InChiKey: FKIRSCKRJJUCNI-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C(Solv: ethanol (64-17-5))
• 沸点：
  394.7±22.0 °C(Predicted)
• 密度：
  1.554±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 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：
  H315,H319,H335
• 储存条件：
  存放在室温、干燥且密封的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 7-bromo-1H-indole-2-carboxylate
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: Ethyl 7-bromo-1H-indole-2-carboxylate
CAS number: 16732-69-7

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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, 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: C11H10BrNO2
Molecular weight: 268.1

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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 bromide.

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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

7-溴-1H-吲哚-2-甲酸乙酯是一种有机中间体，可通过2-溴苯基肼与丙酮酸乙酯反应关环制备得到。

反应信息

• 作为反应物：
  描述：

  7-溴-1H-吲哚-2-甲酸乙酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 甲醇 、 sodium hydride 、 1-丙基磷酸酐 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 80.0 ℃ 、200.0 kPa 条件下， 反应 33.58h， 生成 methyl 2-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylcarbamoyl)-1-methyl-1H-indole-7-carboxylate
  参考文献：
  名称：

  7-(Piperazine-1-Ymethyl)-1H-Indole-2-Carboxylic Acid (Phenyl)-Amide Derivatives and Allied Compounds as P38 Map Kinase Inhibitors for the Treatment of Respiratory Diseases

  摘要：

  本发明提供了根据通用公式(I)的化合物，这些化合物被建议用于治疗呼吸系统疾病，特别是哮喘和慢性阻塞性肺病(COPD)。

  公开号：

  US20110269737A1
• 作为产物：
  描述：

  2-溴苯肼盐酸盐 在 对甲苯磺酸 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 7-溴-1H-吲哚-2-甲酸乙酯
  参考文献：
  名称：

  7-(Piperazine-1-Ymethyl)-1H-Indole-2-Carboxylic Acid (Phenyl)-Amide Derivatives and Allied Compounds as P38 Map Kinase Inhibitors for the Treatment of Respiratory Diseases

  摘要：

  本发明提供了根据通用公式(I)的化合物，这些化合物被建议用于治疗呼吸系统疾病，特别是哮喘和慢性阻塞性肺病(COPD)。

  公开号：

  US20110269737A1

文献信息

• Piperazine derivatives
  申请人：——

  公开号：US20020169163A1

  公开（公告）日：2002-11-14

  Piperazine derivatives, as well as pharmaceutically acceptable salts, solvates and esters thereof, can be used in the form of pharmaceutical preparations for the treatment or prevention of disorders of the central nervous system, damage to the central nervous system, cardiovascular disorders, gastrointestinal disorders, diabetes insipidus, type II diabetes, obesity and sleep apnoea.

  哌嗪衍生物以及其中医药可接受的盐、溶剂合物和酯，可用于制药制剂的形式，用于治疗或预防中枢神经系统疾病、中枢神经系统损伤、心血管疾病、胃肠疾病、尿崩症、2型糖尿病、肥胖和睡眠呼吸暂停。
• [EN] SUBSTITUTED INDOLE MCL-1 INHIBITORS<br/>[FR] INHIBITEURS D'INDOLES MCL-1 SUBSTITUÉS
  申请人：UNIV VANDERBILT

  公开号：WO2017152076A1

  公开（公告）日：2017-09-08

  The present disclosure provides for compounds that inhibit the activity of an anti- apoptotic Bcl-2 family member Myeloid cell leukemia-1 (Mcl-1) protein. The present disclosure also provides for pharmaceutical compositions as well as methods for using compounds for treatment of diseases and conditions (e.g., cancer) characterized by the over- expression or dysregulation of Mcl-1 protein.

  本公开提供了抑制抗凋亡Bcl-2家族成员髓细胞白血病-1（Mcl-1）蛋白活性的化合物。本公开还提供了用于治疗由Mcl-1蛋白过度表达或失调所特征的疾病和病况（例如癌症）的药物组合物以及使用化合物的方法。
• Anti-obesity 1,2,3,4,10,10-a-hexahydropy razino [1,2-a] indoles
  申请人：——

  公开号：US20020035110A1

  公开（公告）日：2002-03-21

  The present invention is directed to 1,2,3,4,10,10a,-hexahydropyrazino[1,2-a] indole derivatives as well as pharmaceutically acceptable salts, solvates and esters thereof, wherein R 1 to R 8 have the significance given in claim 1 be used in the form of pharmaceutical preparations for the treatment or prevention of disorders of the central nervous system, damage to the central nervous system, cardiovascular disorders, gastrointestinal disorders, diabetes insipidus, obesity and sleep apnea.

  本发明涉及1,2,3,4,10,10a,-六氢吡唑[1,2-a]吲哚衍生物以及药用可接受的盐、溶剂合物和酯，其中R1至R8具有如权利要求1中所述的意义，用于以药物制剂的形式治疗或预防中枢神经系统疾病、中枢神经系统损伤、心血管疾病、胃肠疾病、尿崩症、肥胖和睡眠呼吸暂停。
• [EN] SPIROCYCLOHEPTANES AS INHIBITORS OF ROCK<br/>[FR] SPIROCYCLOHEPTANES UTILISÉS EN TANT QU'INHIBITEURS DE ROCK
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016010950A1

  公开（公告）日：2016-01-21

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically-acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了式(I)的化合物：或立体异构体、互变异构体或药用可接受的盐，其中所有变量均如本文所述定义。这些化合物是选择性的ROCK抑制剂。本发明还涉及包含这些化合物的药物组合物，以及使用同一化合物治疗心血管、平滑肌、肿瘤学、神经病理学、自身免疫、纤维化和/或炎症性疾病的方法。
• CBI analogues of the duocarmycins and CC-1065
  申请人：Boger L. Dale

  公开号：US20050026987A1

  公开（公告）日：2005-02-03

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC 50 =2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp 2 , sp 3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.

  一系列广泛的CBI类似物，包括二聚卡蜜素和CC-1065的类似物，探索了第一个吲哚DNA结合亚基中取代基效应的细节。一般来说，在吲哚C5位置的取代导致细胞毒性增强，可以达到≧1000倍，提供了更强效（IC50=2-3 pM）的含有单个DNA结合亚基的简化类似物，比CBI-TMI、二聚卡蜜素SA或CC-1065更有效。细胞毒性增加与DNA烷基化速率和效率的增加密切相关。与基于DSA或CPI的类似物相比，这种效应在CBI类似物中更为显著。此外，这种效应对于C5取代基的电子性质不太敏感，但对于取代基的大小、刚性长度和形状（sp、sp2、sp3杂化）敏感，这与预期一致，即这种影响仅仅是由于其存在。