6-溴-4-吲哚甲酸甲酯 | 107650-22-6

• 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: 6-溴-4-吲哚甲酸甲酯
• 中文别名: 甲基6-溴吲哚-4-甲酸酯；6-溴-1H-吲哚-4-甲酸甲酯
• 英文名称: methyl 6-bromo-1H-indole-4-carboxylate
• 英文别名: methyl 6-bromo-4-indolecarboxylate；6-bromo-1H-indole-4-carboxylic acid methyl ester；methyl 6-bromoindole-4-carboxylate
• CAS: 107650-22-6
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: KPFSQBKJYHWFME-UHFFFAOYSA-N

物化性质

• 沸点：
  382.6±22.0 °C(Predicted)
• 密度：
  1.629

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：
  室温、密封保存，并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-4-indolecarboxylic acid methyl ester
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: 6-Bromo-4-indolecarboxylic acid methyl ester
CAS number: 107650-22-6

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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: C10H8BrNO2
Molecular weight: 254.1

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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：

  6-溴-4-吲哚甲酸甲酯 在 N-甲基吗啉 、 环丁砜 、 N-羟基-7-氮杂苯并三氮唑 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium hydride 、 sodium carbonate 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 对甲苯磺酰肼 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 正庚烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 119.5h， 生成 EZH2甲基转移酶抑制剂(GSK126)
  参考文献：
  名称：

  US2014/256739

  摘要：

  公开号：
• 作为产物：
  描述：

  2-甲基-3-硝基苯甲酸 在 1,3-二溴-5,5-二甲基海因 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 6-溴-4-吲哚甲酸甲酯
  参考文献：
  名称：

  [EN] SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE
  [FR] INHIBITEURS SÉLECTIFS DE MUTANTS CLINIQUEMENT IMPORTANTS DE LA TYROSINE KINASE DE L'EGFR

  摘要：

  本发明提供了式（I）的化合物或其亚类结构或种属，或其药学上可接受的盐、酯、溶剂化合物和/或前药，以及用于治疗或改善异常细胞增殖性疾病，如癌症的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。

  公开号：

  WO2019010295A1

文献信息

• BICYCLIC HETEROARYL COMPOUNDS AND USES THEREOF
  申请人：Revolution Medicines, Inc.

  公开号：US20210139517A1

  公开（公告）日：2021-05-13

  The present disclosure is directed to modulators of SOS1 and their use in the treatment of disease. Also disclosed are pharmaceutical compositions comprising the same.

  本公开涉及SOS1的调节剂及其在治疗疾病中的应用。还公开了包含相同成分的药物组合物。
• [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。
• Development and Scale-up of Continuous Electrocatalytic Hydrogenation of Functionalized Nitro Arenes, Nitriles, and Unsaturated Aldehydes
  作者：Jonathan D. Egbert、Edwin C. Thomsen、Stacy A. O’Neill-Slawecki、Douglas M. Mans、David C. Leitch、Lee J. Edwards、Charles E. Wade、Robert S. Weber

  DOI：10.1021/acs.oprd.8b00379

  日期：2019.9.20

  on the filter-press architecture of redox flow batteries have proven to be effective and scalable toward the production of commercially relevant, pharmaceutical quantities of anilines (>500 kg/year) from halogen-, hydroxyl-, and carbonyl-substituted nitroarenes. Turbulent flow through the carbon felts on which the catalysts were supported facilitated scaling toward production levels because it conferred

  事实证明，基于氧化还原液流电池压滤架构的电解流反应器可有效且可扩展地用于由卤素，羟基和羰基取代生产与商业相关的药学量的苯胺（> 500 kg /年）硝基芳烃。流过负载有催化剂的碳毡的湍流有助于向生产水平扩展，因为它赋予了反应器与规模无关的，类似于塞流的停留时间分布和较高的传质系数。在池中配备微参比电极可以将最初在间歇系统中开发的反应条件转移到连续流反应器中。
• [EN] ANTIBIOTIC COMPOUNDS, PHARMACEUTICAL FORMULATIONS THEREOF AND METHODS AND USES THEREFOR<br/>[FR] COMPOSÉS ANTIBIOTIQUES, LEURS FORMULATIONS PHARMACEUTIQUES, AINSI QUE PROCÉDÉS ASSOCIÉS ET UTILISATIONS ASSOCIÉES
  申请人：UNIV FRASER SIMON

  公开号：WO2017075694A1

  公开（公告）日：2017-05-11

  The present invention relates to compounds of formula (I) wherein G1 to G8 are as defined herein. The compounds are PK inhibitors and as such represent a new approach to treating pathogenic infections, including multidrug resistant pathogens. Disclosed herein are the compounds of formula (I), pharmaceutical compositions comprising the compounds of formula (I) and their use in the treatment of antimicrobial infection. (Formula (1))

  本发明涉及式(I)的化合物，其中G1至G8如本文所定义。这些化合物是PK抑制剂，因此代表了治疗病原体感染的新方法，包括多药耐药病原体。本文披露了式(I)的化合物，包括含有式(I)的药物组合物以及它们在抗微生物感染治疗中的应用。
• Novel Pyrrolopyridone Bromodomain and Extra-Terminal Motif (BET) Inhibitors Effective in Endocrine-Resistant ER+ Breast Cancer with Acquired Resistance to Fulvestrant and Palbociclib
  作者：Yangfeng Li、Jiong Zhao、Lauren M. Gutgesell、Zhengnan Shen、Kiira Ratia、Katherine Dye、Oleksii Dubrovskyi、Huiping Zhao、Fei Huang、Debra A. Tonetti、Gregory R. J. Thatcher、Rui Xiong

  DOI：10.1021/acs.jmedchem.0c00456

  日期：2020.7.9

  cells than six BET inhibitors in clinical trials. Transcriptomic analysis differentiated 27 from the benchmark BETi, JQ-1, showing downregulation of oncogenes and upregulation of tumor suppressors and apoptosis. The therapeutic approach was validated by oral administration of 27 in orthotopic xenografts of endocrine-resistant breast cancer in monotherapy and in combination with fulvestrant. Importantly

  对氟维司群和palbociclib的获得性耐药是治疗雌激素受体阳性（ER +）乳腺癌的新挑战。ER以大多数电阻设置表示；因此，靶向BET扩增的ER介导的转录的溴结构域和末端外蛋白抑制剂（BETi）具有治疗潜力。新型吡咯并吡啶酮BETi利用与L92 / L94的新型相互作用，该相互作用通过与BRD4的共晶结构确定为27。在耐内分泌剂，耐palbociclib和ESR1突变的细胞系中证实了在抗氟司韦特（MCF-7：CFR）细胞中使用生长抑制来优化BETi 。在临床试验中，27种在MCF-7：CFR细胞中比六种BET抑制剂更有效。转录组学分析与众不同27来自基准BETi JQ-1的数据显示癌基因的下调，肿瘤抑制因子和细胞凋亡的上调。通过单药治疗和氟维司群联合口服治疗内分泌抗性乳腺癌的原位异种移植物中的27种药物，验证了该治疗方法的有效性。重要的是，在大鼠中当量剂量下，血小板减少症得到缓解。