5-溴-1H-吲哚-3-甲酸 | 10406-06-1

• 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-溴-1H-吲哚-3-甲酸
• 中文别名: 5-溴吲哚-3-羧酸；5-溴吲哚-3-甲酸
• 英文名称: 5-bromo-1H-indole-3-carboxylic acid
• 英文别名: 5-bromoindole-3-carboxylic acid
• CAS: 10406-06-1
• 化学式: C₉H₆BrNO₂
• mdl: MFCD05664007
• 分子量: 240.056
• InChiKey: JVZMBSGNSAHFCY-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C (decomp)
• 沸点：
  240°C(lit.)
• 密度：
  1.838±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存于室温、避光且在惰性气体环境中

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-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: 5-Bromo-1H-indole-3-carboxylic acid
CAS number: 10406-06-1

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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: C9H6BrNO2
Molecular weight: 240.1

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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

反应信息

• 作为反应物：
  描述：

  5-溴-1H-吲哚-3-甲酸 在 盐酸 、 DPPA 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 5-溴-1H-吲哚-3-胺
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY
  [FR] COMPOSÉS ET COMPOSITIONS POUR TRAITER DES ÉTATS PATHOLOGIQUES ASSOCIÉS À UNE ACTIVITÉ DE STING

  摘要：

  这份披露涉及一些化学实体（例如，一种化合物或一种药用可接受的盐，和/或水合物，和/或共晶体，和/或前药，和/或互变异构体，和/或该化合物的药物组合），可以抑制（例如，对抗）干扰素基因刺激器（STING）。这些化学实体可用于治疗某些情况、疾病或障碍，其中增加（例如，过度）STING激活（例如，STING信号传导）导致该情况、疾病或障碍的病理和/或症状和/或进展（例如，癌症）在受试者（例如，人类）中。这份披露还涉及包含相同化学实体的组合物，以及使用和制备这些组合物的方法。公式（I）。

  公开号：

  WO2021067801A1
• 作为产物：
  描述：

  5-溴吲哚-3-甲醛 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 6.5h， 以65%的产率得到5-溴-1H-吲哚-3-甲酸
  参考文献：
  名称：

  2,5-双(吲哚基)-1,3,4-恶二唑、诺托普森汀类似物的合成、抗癌评价和分子对接研究

  摘要：

  摘要 设计合成了10种新型2,5-双(吲哚基)-1,3,4-恶二唑类化合物。使用 MTT 还原试验评估了所有这些化合物对四种癌细胞系即 A549、MDA-MB-231、MCF-7 和 HeLa 的细胞毒性。其中，化合物12e对MCF-7细胞系表现出良好的细胞毒性，IC50值为1.8 μM，与标准药物多柔比星（IC50值为0.98 μM）相比，它被确定为有前景的药物先导物。化合物12h对三种癌细胞系，即肺（A549）、乳腺（MCF-7）和宫颈（HeLa）表现出更好的抗肿瘤活性，IC50值分别为3.3 μM、2.6 μM和6.34 μM。

  DOI：

  10.1016/j.molstruc.2020.127875

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。
• [EN] TRIAZOLONE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE TRIAZOLONE ET LEURS UTILISATIONS
  申请人：INCEPTION 2 INC

  公开号：WO2013134562A1

  公开（公告）日：2013-09-12

  The invention disclosed herein is directed to compounds of Formula (I) and pharmaceutically acceptable salts thereof, which are useful in the treatment of prostate, breast, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention also comprises pharmaceutical compositions comprising a therapeutically effective amount of compound of Formula (I), or a pharmaceutically acceptable salt thereof. The invention disclosed herein is also directed to methods of treating prostate, breast, ovarian, liver, kidney, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention disclosed herein is further directed to methods of treating prostate, breast, colon, pancreatic, chronic lymphocytic leukemia, melanoma and other cancers comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist. The compounds and pharmaceutical compositions of the invention are also useful in the treatment of viral infections, such as HCV infections and HIV infections. The invention disclosed herein is also directed to a methods of preventing the onset of and/or recurrence of acute and chronic myeloid leukemia, as well as other cancers, comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist.

  本发明涉及的化合物属于式(I)及其药学上可接受的盐，可用于治疗前列腺、乳腺、结肠、胰腺、人类慢性淋巴细胞白血病、黑色素瘤和其他癌症。该发明还包括含有式(I)化合物的治疗有效量或其药学上可接受的盐的药物组合物。本发明还涉及治疗前列腺、乳腺、卵巢、肝脏、肾脏、结肠、胰腺、人类慢性淋巴细胞白血病、黑色素瘤和其他癌症的方法。本发明还涉及治疗前列腺、乳腺、结肠、胰腺、慢性淋巴细胞白血病、黑色素瘤和其他癌症的方法，包括给予选择性PPARα拮抗剂的治疗有效量。本发明的化合物和药物组合物还可用于治疗病毒感染，如HCV感染和HIV感染。本发明还涉及一种预防急性和慢性骨髓性白血病以及其他癌症发作和/或复发的方法，包括给予选择性PPARα拮抗剂的治疗有效量。
• Heteroaromatic Carboxamide Derivatives as Plasma Kallikrein Inhibitors
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20200054617A1

  公开（公告）日：2020-02-20

  Heteroaromatic carboxamides of formula (I), wherein Y, R, and X are as defined herein, and pharmaceutically acceptable salts thereof. The compounds of formula (I) can be used in methods for the treatment of diseases which can be influenced by inhibition of plasma kallikrein.

  式(I)的杂环芳基羧酰胺，其中Y、R和X如本文所定义，并其药学上可接受的盐。式(I)的化合物可用于治疗受血浆激肽酶抑制影响的疾病的方法。
• Synthesis and Biological Evaluation of 2‐Arylamino‐5‐ (3′‐Indolyl)‐1,3,4‐Oxadiazoles as Potent Cytotoxic Agents
  作者：Mukund P Tantak、Anil Kumar、Brett Noel、Kavita Shah、Dalip Kumar

  DOI：10.1002/cmdc.201300221

  日期：2013.9

  scaffolds in medicinal chemistry, the indole and 1,3,4‐oxadiazole ring systems, gave rise to 2‐arylamino‐5‐(3′‐indolyl)‐1,3,4‐oxadiazoles with IC50 values in the nanomolar range against a panel of tumor cell lines. Preliminary structure–activity relationship studies indicate potential for improved selectivity through further manipulation of the oxadiazole C‐2 and C‐5 positions.

  合理简单：药物化学中的两个关键支架，吲哚和 1,3,4-恶二唑环系统的偶联产生具有 IC 的 2-芳基氨基-5-(3'-吲哚基)-1,3,4-恶二唑针对一组肿瘤细胞系，在纳摩尔范围内有50 个值。初步的构效关系研究表明，通过进一步操纵恶二唑 C-2 和 C-5 位置可以提高选择性。
• PYRIMIDINE COMPOUND, PREPARATION METHOD THEREOF AND MEDICAL USE THEREOF
  申请人：Ancureall Pharmaceutical (Shanghai) Co., Ltd.

  公开号：US20210101881A1

  公开（公告）日：2021-04-08

  The present invention discloses a pyrimidine compound, a preparation method thereof and a medical use thereof. Specifically, the present invention discloses a pyrimidine compound represented by formula (I), pharmaceutically acceptable salts thereof, a preparation method thereof, and a use thereof as a cyclin-dependent kinase 9 (CDK9) inhibitor, particularly for the treatment of cancer. The definition of each group in formula (I) is the same as that in the specification.

  本发明公开了一种嘧啶化合物，其制备方法及医药用途。具体地，本发明公开了一种由式(I)表示的嘧啶化合物，其药学上可接受的盐，其制备方法，以及作为细胞周期依赖性激酶9（CDK9）抑制剂的用途，特别用于癌症治疗。式(I)中每个基团的定义与规范中的相同。