1-(苯磺酰基)-5-溴-3-碘吡咯并[2,3-b]吡啶 | 757978-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(苯磺酰基)-5-溴-3-碘吡咯并[2,3-b]吡啶
• 中文别名: 1-(苯磺酰基)-5-溴-3-碘-1H-吡咯并[2,3-b]吡啶
• 英文名称: 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 1-(benzenesulfonyl)-5-bromo-3-iodo-pyrrolo[2,3-b]pyridine；1-benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine；3-iodo-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine；1-(benzenesulfonyl)-5-bromo-3-iodopyrrolo[2,3-b]pyridine
• CAS: 757978-19-1
• 化学式: C₁₃H₈BrIN₂O₂S
• 分子量: 463.093
• InChiKey: BVYHANZXUBVRRV-UHFFFAOYSA-N

物化性质

• 沸点：
  555.2±60.0 °C(Predicted)
• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件：2-8℃，需密封保存并在干燥处存放。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Benzenesulfonyl-5-bromo-3-iodo-1h-pyrrolo[2,3-b]pyridine
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: 1-Benzenesulfonyl-5-bromo-3-iodo-1h-pyrrolo[2,3-b]pyridine
CAS number: 757978-19-1

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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: C13H8BrIN2O2S
Molecular weight: 463.1

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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, hydrogen Iodide, sulfur
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

反应信息

• 作为反应物：
  描述：

  1-(苯磺酰基)-5-溴-3-碘吡咯并[2,3-b]吡啶 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 5-bromo-3-(4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Structure-based de novo design and identification of D816V mutant-selective c-KIT inhibitors

  摘要：

  通过使用改进的精确溶剂自由能的评分函数进行基于结构的全新设计，确定了具有纳摩尔抑制活性和对功能获得性D816V突变体高选择性的新型7-氮杂吲哚基c-KIT抑制剂。

  DOI：

  10.1039/c4ob00053f
• 作为产物：
  描述：

  5-溴-7-氮杂吲哚 在 苄基三乙基氯化铵 、 sodium hydride 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(苯磺酰基)-5-溴-3-碘吡咯并[2,3-b]吡啶
  参考文献：
  名称：

  3,5-Diarylazaindoles as DYRK1A Protein Inhibitors for the Treatment of Cognitive Deficiencies Associated with Down's Syndrome and with Alzheimer's Disease

  摘要：

  本发明涉及一种具有以下结构的化合物（I′）或其药学上可接受的盐、溶剂或水合物，其中：X3为F、OH或SH，Y3为F、OH或SH，X1、X2、X4、X5、Y1、Y2、Y4和Y5分别独立地为H、F、Cl、Br、OH或SH，且在X1、X2、X4和X5基团中的1到2个基团不是H，和/或在Y1、Y2、Y4和Y5基团中的1到2个基团不是H。本发明还涉及一种具有结构式（I′）的化合物，用作药物，特别是用于预防和/或治疗与Dyrk1A蛋白功能障碍相关的认知障碍。

  公开号：

  US20150307492A1

文献信息

• TBK/IKK INHIBITOR COMPOUNDS AND USES THEREOF
  申请人：Merck Patent GmbH

  公开号：US20160376283A1

  公开（公告）日：2016-12-29

  The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as TBK/IKKε inhibitors.

  本发明涉及式I化合物及其药用可接受的组合物，用作TBK/IKKε抑制剂。
• 氮杂吲哚衍生物髓细胞增殖抑制剂及其制备方法与在制药中的应用
  申请人：复旦大学

  公开号：CN113214247A

  公开（公告）日：2021-08-06

  本发明提供式I所示的氮杂吲哚衍生物髓细胞增殖抑制剂，其中R1,R2,R33均具有本发明说明书中所限定的含义。式I化合物可显著抑制以MOLM‑16，HL‑60，MV‑4‑11为代表的髓细胞增殖及其相关病症。本发明提供的式I或其盐或相关药物组合，具有优异的体内外抑制活性、良好的成药性，且生物利用度高，对脏器无明显损伤。因此，式I或其盐及相关药物组合具有巨大的临床应用前景。
• 3-CYANOARYL-1H-PYRROLO[2,3-B]PYRIDINE DERIVATIVES
  申请人：MERCK PATENT GMBH

  公开号：US20140323481A1

  公开（公告）日：2014-10-30

  Compounds of the formula (I) in which R 1 , R 2 , X and Y have the meanings indicated in claim 1 , are inhibitors of TBK1 and IKKε and can be employed, inter alia, for the treatment of cancer and inflammatory diseases.

  式（I）中R1、R2、X和Y具有权利要求1中指示的含义的化合物，是TBK1和IKKε的抑制剂，可用于治疗癌症和炎症性疾病。
• Discovery of a Novel Series of 7-Azaindole Scaffold Derivatives as PI3K Inhibitors with Potent Activity
  作者：Chengbin Yang、Xi Zhang、Yi Wang、Yongtai Yang、Xiaofeng Liu、Mingli Deng、Yu Jia、Yun Ling、Ling-hua Meng、Yaming Zhou

  DOI：10.1021/acsmedchemlett.7b00222

  日期：2017.8.10

  inhibitors potently inhibit the signaling pathway of PI3K/AKT/mTOR, which provides a promising new approach for the molecularly targeted cancer therapy. In this work, a novel series of 7-azaindole scaffold derivatives was discovered by the fragment-based growing strategy. The structure–activity relationship profiles identified that the 7-azaindole scaffold derivatives exhibit potent activity against PI3K

  磷酸肌醇3-激酶（PI3K）抑制剂有效抑制PI3K / AKT / mTOR的信号传导途径，这为分子靶向癌症治疗提供了一种有希望的新方法。在这项工作中，通过基于片段的生长策略发现了一系列新型的7-氮杂吲哚支架衍生物。结构-活性之间的关系曲线表明，7-氮杂吲哚支架衍生物在分子和细胞水平上均表现出对PI3K的有效活性，并在一组人类肿瘤细胞中表现出细胞增殖作用。
• Compounds and methods for kinase modulation, and indications therefor
  申请人：Plexxikon Inc.

  公开号：US09096593B2

  公开（公告）日：2015-08-04

  Compounds and salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof and uses thereof are described. In certain aspects and embodiments, the described compounds or salts thereof, formulations thereof, conjugates thereof, derivatives thereof, or forms thereof are active on Fms protein kinase, or on Fms and Kit protein kinase, or on Fms and Flt-3 protein kinase. Also described are methods of use thereof to treat diseases and conditions, including diseases and conditions associated with activity of Fms protein kinase, Kit protein kinase, or Flt-3 protein kinase including rheumatoid arthritis, osteoarthritis, multiple sclerosis, Alzheimer's disease, Parkinson's disease, glomerulonephritis, interstitial nephritis, Lupus nephritis, tubular necrosis, diabetic nephropathy, renal hypertrophy, acute myeloid leukemia, melanoma, multiple myeloma, metastatic breast cancer, prostate cancer, pancreatic cancer, neurofibromatosis, brain metastases, and gastrointestinal stromal tumors.

  描述了化合物及其盐，制剂，共轭物，衍生物，形式和用途。在某些方面和实施方式中，所述的化合物或其盐，制剂，共轭物，衍生物或形式对Fms蛋白激酶，或对Fms和Kit蛋白激酶，或对Fms和Flt-3蛋白激酶具有活性。还描述了使用方法，用于治疗与Fms蛋白激酶，Kit蛋白激酶或Flt-3蛋白激酶活性相关的疾病和状况，包括类风湿性关节炎，骨关节炎，多发性硬化症，阿尔茨海默病，帕金森病，肾小球肾炎，间质性肾炎，狼疮性肾炎，小管坏死，糖尿病肾病，肾肥大，急性髓性白血病，黑色素瘤，多发性骨髓瘤，转移性乳腺癌，前列腺癌，胰腺癌，神经纤维瘤病，脑转移和胃肠间质瘤。