6-溴咪唑并[1,2-a]吡啶-2-羧酸乙酯 | 67625-37-0

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 6-溴咪唑并[1,2-a]吡啶-2-羧酸乙酯
• 中文别名: 6-溴咪唑并[1,2-A]砒啶-2-羧酸乙酯
• 英文名称: ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate
• CAS: 67625-37-0
• 化学式: C₁₀H₉BrN₂O₂
• mdl: MFCD06659034
• 分子量: 269.098
• InChiKey: MWDCKDQQAFZDOH-UHFFFAOYSA-N

物化性质

• 熔点：
  69-72℃
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 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：
  储存条件：2-8°C，密封保存，并确保干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate
Ingredient name:
CAS number: 67625-37-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H9BrN2O2
Molecular weight: 269.1

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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-溴咪唑并[1,2-a]吡啶-2-羧酸乙酯 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到6-bromoimidazo[1,2-a]pyridine-2-carboxamide
  参考文献：
  名称：

  仿生咪唑并[1,2-a:4,5-c']双吡啶在人类癌细胞中具有双重抗增殖和抗迁移特性：SAR调查

  摘要：

  在此，我们报告了新型仿生咪唑并[1,2- a :4,5 c' ]联吡啶的设计、合成和评估。结构优化确定了四种抗增殖化合物。化合物11，18，19和20表现出优异的抗癌活性的体外与IC 50 0.4-5μM针对三种人癌细胞系的（MDA-MB-468，MDA-MB-435S和MDA-MB-231）。这四种化合物诱导的细胞凋亡中的MDA-MB-231细胞以剂量依赖的方式，针对不同的细胞凋亡蛋白表达：11增加促凋亡Bax蛋白表达而18 - 20降低抗凋亡 Bcl-2 蛋白的水平。通过 Ki-67 染色测量，化合物18和19还降低了 MDA-MB-231 细胞增殖。 此外，还测试了化合物在高度侵袭性的人类 MDA-MB-435s 细胞系中抑制细胞迁移的能力。该系列的六种化合物 ( 8, 15, 18, 22, 23, 24 ) 抑制了 41–50% 的细胞迁移，而四种化合物 ( 20 , 25 , 27

  DOI：

  10.1016/j.ejmech.2021.113258
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 、 3-溴丙酮酸乙酯 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以80.6%的产率得到6-溴咪唑并[1,2-a]吡啶-2-羧酸乙酯
  参考文献：
  名称：

  一种新化合物 6-(2-氟苯基)-N-(对甲苯基)Imidazo[1,2-A]Pyridine-2-Carboxamide 的合成、晶体结构和 DFT 研究

  摘要：

  6-(2-氟苯基)-N-(对甲苯基)咪唑并[1,2-a]吡啶-2-甲酰胺是一种具有氮杂双环和酰胺基团功能的有机中间体。本文通过闭环反应、铃木反应、水解和酰胺化反应得到标题化合物。化合物的结构通过FT-IR、1H NMR、13C NMR光谱和MS确认。同时，标题化合物的单晶通过 X 射线衍射测量并进行晶体学和构象分析。使用密度泛函理论 (DFT) 进一步计算分子结构，并与 X 射线衍射值进行比较。构象分析结果表明，DFT优化的分子结构与单晶X射线衍射确定的晶体结构一致。此外，

  DOI：

  10.1134/s0022476619120072

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE PRMT5
  申请人：JUBILANT BIOSYS LTD

  公开号：WO2019102494A1

  公开（公告）日：2019-05-31

  The compounds of Formula I, Formula Ia, and Formula Ib are described herein along with their analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites, and prodrugs thereof. These compounds inhibit PRMT5 and are useful as therpeautic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, schizophrenia, Alzheimer's disease, Parkinson's disease and the like.

  公式I、公式Ia和公式Ib的化合物以及它们的类似物、互变异构体、对映异构体、多态性、水合物、溶剂化物、药物可接受的盐、药物组合物、代谢物和前药在本文件中进行了描述。这些化合物抑制PRMT5，并可作为治疗或改善与细胞生长相关的疾病，如恶性肿瘤、精神分裂症、阿尔茨海默病、帕金森病等的治疗或改善剂。
• Design, Synthesis, and Biological Evaluation of Imidazo[1,2-<i>a</i>]pyridine Derivatives as Novel PI3K/mTOR Dual Inhibitors
  作者：Ya’nan Yu、Yuqiao Han、Fupo Zhang、Zhenmei Gao、Tong Zhu、Suzhen Dong、Mingliang Ma

  DOI：10.1021/acs.jmedchem.9b01736

  日期：2020.3.26

  no PI3K/mTOR dual inhibitor has been approved by the FDA yet. Therefore, it is still essential to discover a candidate with good efficacy and low toxicity. In our design, a series of imidazo[1,2-a]pyridine derivatives had been synthesized and subjected to activity assessment in vitro and in vivo. 15a was proved to be a potent PI3K/mTOR dual inhibitor with excellent kinase selectivity, modest plasma

  PI3K-Akt-mTOR信号传导途径已被验证为癌症治疗的有效靶向途径。但是，尚未有FDA批准PI3K / mTOR双抑制剂。因此，寻找具有良好疗效和低毒性的候选药物仍然至关重要。在我们的设计中，已合成了一系列咪唑并[1,2-a]吡啶衍生物，并进行了体内和体外活性评估。15a被证明是一种有效的PI3K / mTOR双重抑制剂，具有出色的激酶选择性，适度的血浆清除率和可接受的口服生物利用度。此外，15a在HCT116和HT-29异种移植物中显示出对肿瘤生长的显着抑制作用，而对体重没有明显影响。
• [EN] FUSED TRICYCLIC IMIDAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY<br/>[FR] DÉRIVÉS D'IMIDAZOLE TRICYCLIQUE CONDENSÉ COMME MODULATEURS DE L'ACTIVITÉ DU TNF
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2015086526A1

  公开（公告）日：2015-06-18

  A series of fused tricyclic imidazole derivatives, in particular dihydro-1H-cyclopenta[4,5]imidazo[1,2-a]pyridine derivatives, and analogues thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

  一系列融合的三环咪唑衍生物，特别是二氢-1H-环戊[4,5]咪唑[1,2-a]吡啶衍生物及其类似物，作为人类肿瘤坏死因子α活性的强力调节剂，因此在治疗和/或预防各种人类疾病方面具有益处，包括自身免疫和炎症性疾病；神经和神经退行性疾病；疼痛和痛觉障碍；心血管疾病；代谢性疾病；眼科疾病；以及肿瘤学疾病。
• [EN] BENZOFUROPYRIMIDINONES AS PROTEIN KINASE INHIBITORS<br/>[FR] BENZOFUROPYRIMIDINONES EN TANT QU'INHIBITEURS DE PROTÉINE KINASE
  申请人：EXELIXIS INC

  公开号：WO2009086264A1

  公开（公告）日：2009-07-09

  A compound according to formula I: or a pharmaceutically acceptable salt thereof; wherein R1, R2, R3a, R3b, R3c and R3d are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

  根据公式I的化合物：或其药用可接受盐；其中R1、R2、R3a、R3b、R3c和R3d如规范中所定义，以及其药物组合物和使用方法。
• OXAZOLIDINONE DERIVATIVE HAVING FUSED RING
  申请人：Katoh Issei

  公开号：US20110098471A1

  公开（公告）日：2011-04-28

  The present invention provides a novel antimicrobial drug comprising an oxazolidinone derivative of the formula (I): or a pharmaceutically acceptable salt or solvate thereof; wherein ring A is ring B is a benzene ring optionally substituted with lower alkyl; ring C is an optionally substituted six-membered heterocycle containing at least one nitrogen atom and one to three double bond(s) in the ling wherein the atom at the point of attachment to ring B is a carbon atom; ring D is an optionally substituted five-membered ring containing one or two double bond(s) in the ring; A 1 and A 2 are independently nitrogen or carbon; m is 0 or 1; R represents H, —NHC(═O)R A , —NHC(═S)R A , —NH-het 1 , —O-het 1 , —S-het 1 , —S(═O)-het 1 , —S(═O) 2 -het 1 , het 2 , —CONHR A , —OH, lower alkyl, lower alkoxy or lower alkenyl; and het 1 and het 2 are independently a heterocyclic group; with the proviso that the fused ring C-D is not

  本发明提供了一种新型抗菌药物，包括式(I)的噁唑烷酮衍生物： 或其药学上可接受的盐或溶剂；其中环A是 环B是一个苯环，可选择地取代为较低的烷基；环C是一个可选择地取代的含有至少一个氮原子和一个到三个双键的六元杂环，在连接到环B的点的原子是一个碳原子；环D是一个可选择地取代的含有一个或两个双键的五元环；A 1 和A 2 独立地是氮或碳；m为0或1；R代表H，—NHC(═O)R A ，—NHC(═S)R A ，—NH-het 1 ，—O-het 1 ，—S-het 1 ，—S(═O)-het 1 ，—S(═O) 2 -het 1 ，het 2 ，—CONHR A ，—OH，较低的烷基，较低的烷氧基或较低的烯基；和het 1 和het 2 独立地是一个杂环基团；但附带条件是融合的环C-D不是