6-氯咪唑[1,2-a]吡啶-2-羧酸乙基脂 | 67625-38-1

• 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-氯咪唑[1,2-a]吡啶-2-羧酸乙基脂
• 中文别名: 6-氯咪唑并[1,2-a]吡啶-2-羧酸乙酯；6-氯咪唑并[1,2-A]砒啶-2-羧酸乙酯
• 英文名称: 6-chloroimidazo[1,2-a]pyridine-2-carboxylate
• 英文别名: 6-Chlor-imidazo<1,2-a>pyridin-2-carbonsaeureethylester；6-chloro-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester；ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate
• CAS: 67625-38-1
• 化学式: C₁₀H₉ClN₂O₂
• mdl: MFCD02186220
• 分子量: 224.647
• InChiKey: JWGKTXNASUZJAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114°
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 6-chloroimidazo[1,2-a]pyridine-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 6-chloroimidazo[1,2-a]pyridine-2-carboxylate
CAS number: 67625-38-1

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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.
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: C10H9ClN2O2
Molecular weight: 224.6

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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 chloride.

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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-氯咪唑[1,2-a]吡啶-2-羧酸乙基脂 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 6-氯咪唑并[1,2-a]吡啶-2-甲醛
  参考文献：
  名称：

  Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria

  摘要：

  A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.

  DOI：

  10.1021/acsmedchemlett.9b00515
• 作为产物：
  描述：

  2-氨基-5-氯吡啶 、 3-溴丙酮酸乙酯 以 四氢呋喃 为溶剂， 生成 6-氯咪唑[1,2-a]吡啶-2-羧酸乙基脂
  参考文献：
  名称：

  Palladium‐Catalyzed Regiodivergent C‐H Olefination of Imidazo[1,2a]pyridine Carboxamide and Unactivated Alkenes

  摘要：

  摘要尽管在线性和支链乙烯基（杂）炔合成方面取得了显著的成功，但使用单一催化体系进行的反式 C-H 烯化反应仍未得到充分发展。为了克服这一局限性，本文报道了一种 Pd/MPAA 催化的咪唑并[1,2a] 吡啶羧酰胺与未活化的末端烯的区域发散性 C-H 烯化反应，根据烯的电子性质生成支链和线性烯化产物。此外，该方案还可用于以 D2O 为氘源对相应杂环烯进行 C-H 脱氘反应。初步实验研究和计算研究（DFT 研究）表明，通过烯烃插入和 β-酸酐消除步骤，可以控制区域发散的烯化反应。

  DOI：

  10.1002/chem.202302759

文献信息

• Imidazo\x9b1,2-a!pyridines for the treatment of CNS and cardiac diseases
  申请人：Pharmacia & Upjohn Company

  公开号：US05912246A1

  公开（公告）日：1999-06-15

  The present invention relates to imidazo\x9b1,2-a!pyridine compounds of formula (1) ##STR1## which are dopamine D-4 antagonists and useful as anti-psychotic agents.

  本发明涉及式（1）的咪唑并[1,2-a]吡啶化合物，它们是多巴胺D-4拮抗剂，可用作抗精神病药物。
• [EN] SUBSTITUTED HETEROARYL FUSED DERIVATIVES AS PI3K INHIBITORS<br/>[FR] DÉRIVÉS CONDENSÉS D'HÉTÉROARYLES SUBSTITUÉS À TITRE D'INHIBITEURS DE PI3K
  申请人：INCYTE CORP

  公开号：WO2011075643A1

  公开（公告）日：2011-06-23

  The present invention provides fused derivatives of Formula (I) that modulate the activity of phosphoinositide 3-kinases (PI3Ks) and are useful in the treatment of diseases related to the activity of PBKs including, for example, inflammatory disorders, immune- based disorders, cancer, and other diseases.

  本发明提供了公式（I）的融合衍生物，可调节磷脂酰肌醇3-激酶（PI3Ks）的活性，并在治疗与PBKs活性相关的疾病方面具有用处，例如炎症性疾病、免疫性疾病、癌症和其他疾病。
• Dearomatization of Electron-Deficient Nitrogen Heterocycles via Cobalt-Catalyzed Asymmetric Cyclopropanation
  作者：Amruta Joshi-Pangu、Ryan D. Cohen、Matthew T. Tudge、Yonggang Chen

  DOI：10.1021/acs.joc.6b00322

  日期：2016.4.15

  The dearomatization of a series of electron-deficient nitrogen heterocycles has been achieved through a cobalt-catalyzed asymmetric cyclopropanation reaction. This reaction proceeds with high levels of enantio- and diastereoselectivity to afford unique cyclopropanes that can be further functionalized to provide complex heterocyclic building blocks.

  通过钴催化的不对称环丙烷化反应已实现了一系列电子不足的氮杂环的脱芳香化作用。该反应以高对映体和非对映体选择性进行，得到独特的环丙烷，其可以进一步官能化以提供复杂的杂环结构单元。
• N-HETEROCYCLIC-IMIDAZO[1,2-a]PYRIDINE-2-CARBOXAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
  申请人：PEYRONEL Jean-Francois

  公开号：US20100317673A1

  公开（公告）日：2010-12-16

  Compounds of formula (I): in which: X, R 1 , R 2 , R 3 , and R 4 are as defined in the disclosure, in the form of the base or of an addition salt with an acid; and therapeutic uses thereof.

  式（I）的化合物：其中X、R1、R2、R3和R4如披露中所定义，以碱的形式或与酸形成的加合盐的形式存在；以及它们的治疗用途。
• [EN] 4-[[(7-AMINOPYRAZOLO[1,5-A]PYRIMIDIN-5-YL)AMINO]METHYL]PIPERIDIN-3-OL COMPOUNDS AND THEIR THERAPEUTIC USE<br/>[FR] COMPOSÉS DE 4-[[(7-AMINOPYRAZOLO[1,5-A]PYRIMIDIN-5-YL)AMINO]MÉTHYL]PIPÉRIDIN-3-OL ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：CARRICK THERAPEUTICS LTD

  公开号：WO2021122745A1

  公开（公告）日：2021-06-24

  The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain H-APPAMP compounds (referred to herein as "H-APPAMP compounds") that, inter alia, inhibit cyclin-dependent protein kinases (CDKs), especially CDK12 and/or CDK13, and are selective, for example, for CDK12 and/or CDK13 as compared to CDK7. In addition to selectively inhibiting CDK12 and/or CDK13, the compounds also act as selective Cyclin K degraders thereby removing the key signaling mechanism required for CDK12 and/or CDK13 activation; this confers additional cellular potency and selectivity. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit CDK, especially CDK12 and/or CDK13; and to treat disorders including: disorders that are associated with CDK, especially CDK12 and/or CDK13; disorders that result from an inappropriate activity of a CDK, especially CDK12 and/or CDK13; disorders that are associated with CDK mutation, especially CDK12 and/or CDK13mutation; disorders that are associated with CDK overexpression, especially CDK12 and/or CDK13 overexpression; disorders that are associated with upstream pathway activation of CDK, especially CDK12 and/or CDK13; disorders that are ameliorated by the inhibition of CDK, especially CDK12 and/or CDK13; proliferative disorders; cancer; viral infections (including HIV); neurodegenerative disorders (including Alzheimer's disease and Parkinson's disease); ischaemia; renal diseases; cardiovascular disorders (including atherosclerosis); autoimmune disorders (including rheumatoid arthritis); and disorders caused by dysfunction of translation in cells (including muscular dystrophy). Optionally, the treatment further comprises treatment (e.g., simultaneous or sequential treatment) with a further active agent which is, e.g., an aromatase inhibitor, an anti estrogen, an anti-androgen, a Her2 blocker, a cytotoxic chemotherapeutic agent, an agent stimulating the immune system, a checkpoint inhibitor, a DMA repair inhibitor, etc.

  本发明一般涉及治疗化合物领域。更具体地，本发明涉及某些H-APPAMP化合物（以下简称为“H-APPAMP化合物”），其中包括抑制细胞周期依赖性蛋白激酶（CDKs），特别是CDK12和/或CDK13，并且具有选择性，例如与CDK7相比，对CDK12和/或CDK13有选择性。除了选择性地抑制CDK12和/或CDK13外，这些化合物还作为选择性的Cyclin K降解物，从而去除了CDK12和/或CDK13激活所需的关键信号机制；这赋予了额外的细胞效力和选择性。本发明还涉及包含这些化合物的药物组合物，以及使用这些化合物和组合物，无论是在体外还是在体内，来抑制CDK，特别是CDK12和/或CDK13；以及治疗包括以下疾病的疾病：与CDK有关的疾病，特别是与CDK12和/或CDK13有关的疾病；由于CDK不恰当活性导致的疾病，特别是由于CDK12和/或CDK13不恰当活性导致的疾病；与CDK突变有关的疾病，特别是与CDK12和/或CDK13突变有关的疾病；与CDK过度表达有关的疾病，特别是与CDK12和/或CDK13过度表达有关的疾病；与CDK上游途径激活有关的疾病，特别是与CDK12和/或CDK13上游途径激活有关的疾病；通过抑制CDK改善的疾病，特别是通过抑制CDK12和/或CDK13改善的疾病；增生性疾病；癌症；病毒感染（包括HIV）；神经退行性疾病（包括阿尔茨海默病和帕金森病）；缺血；肾脏疾病；心血管疾病（包括动脉粥样硬化）；自身免疫性疾病（包括类风湿性关节炎）；以及由细胞中翻译功能失调引起的疾病（包括肌肉萎缩症）的疾病。可选地，治疗进一步包括与另一活性药剂的治疗（例如同时或顺序治疗），该药剂可以是芳香化酶抑制剂、抗雌激素、抗雄激素、Her2阻断剂、细胞毒化疗药物、刺激免疫系统的药剂、检查点抑制剂、DNA修复抑制剂等。