6-甲基-2-(4-甲基苯基)咪唑并[1,2-a]吡啶-3-乙酸 | 189005-44-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6-甲基-2-(4-甲基苯基)咪唑并[1,2-a]吡啶-3-乙酸
• 中文别名: 6-甲基-2-(4-甲基苯)咪唑并[1,2A]吡啶-3-乙酸
• 英文名称: 2-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)acetic acid
• 英文别名: 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetic acid；2-(4-methylphenyl)-6-methylimidazo[1,2-a]pyridine-3-acetic acid；[6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-acetic acid；2-[6-Methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid
• CAS: 189005-44-5
• 化学式: C₁₇H₁₆N₂O₂
• mdl: MFCD04114705
• 分子量: 280.326
• InChiKey: JHGHLTNIQXXXNV-UHFFFAOYSA-N

物化性质

• 熔点：
  243-245°C
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（略微加热）、甲醇（略微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.176
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

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：
  -20°C 冰箱

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Methyl-2-(4-methylphenyl)imidazo[1,2-a]-pyridine-3-acetic 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: 6-Methyl-2-(4-methylphenyl)imidazo[1,2-a]-pyridine-3-acetic acid
CAS number: 189005-44-5

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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: C17H16N2O2
Molecular weight: 280.3

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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.

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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-甲基-2-(4-甲基苯基)咪唑并[1,2-a]吡啶-3-乙酸 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 唑吡坦
  参考文献：
  名称：

  硝态烯烃的森田-贝利斯-希尔曼乙酸盐合成咪唑并吡啶并方便地获得毒杀and和唑吡坦

  摘要：

  通过一锅，室温，硝基烯烃的MBH乙酸酯与2-氨基吡啶之间的无试剂反应，已经合成了多种官能化的咪唑并[1,2-a]吡啶。该反应涉及2-氨基吡啶向MBH乙酸酯的级联的分子间双氮杂-Michael加成。我们的方法具有出色的收率，区域选择性以及最重要的是对合成咪唑并吡啶基药物分子（如Alpidem和Zolpidem）的适应性。

  DOI：

  10.1021/ol3020418
• 作为产物：
  描述：

  唑吡坦 在 盐酸 作用下， 以 水 为溶剂， 反应 18.0h， 以94%的产率得到6-甲基-2-(4-甲基苯基)咪唑并[1,2-a]吡啶-3-乙酸
  参考文献：
  名称：

  [EN] IMIDAZO[1,2-A]PYRIDINE ANXIOLYTICS
  [FR] ANXIOLYTIQUES D'IMIDAZO[1,2-A]PYRIDINE

  摘要：

  公开号：

  WO2005044818A3

文献信息

• Structure-based discovery of potent and selective small-molecule inhibitors targeting signal transducer and activator of transcription 3 (STAT3)
  作者：Qiuyao Huang、Yan Zhong、Bingbing Li、Shumin Ouyang、Lin Deng、Jianshan Mo、Shuo Shi、Nan Lv、Ruibo Wu、Peiqing Liu、Wenhao Hu、Xiaolei Zhang、Yuanxiang Wang

  DOI：10.1016/j.ejmech.2021.113525

  日期：2021.10

  of highly potent and selective STAT3 inhibitors, exemplified by compound 39 with the privileged structure of 2-phenylimidazo[1,2-a]pyridine, which selectively inhibits phosphorylation of STAT3 and suppresses subsequent signaling pathway. Moreover, 39 inhibits cell growth, migration and invasion of human triple negative breast cancer (TNBC) cells lines. Consistently, it achieves significant and dose-dependent

  由于其在癌症发生和发展中的重要作用，STAT3 已被证实为有吸引力的抗癌靶点。然而，发现具有类似药物特性的有效且选择性的 STAT3 小分子抑制剂仍然具有挑战性。在这项研究中，通过基于结构的药物发现方法，通过缩合STX-119和SH4-54的特权结构，设计了两个系列的取代 2-苯基喹啉和 2-芳基咪唑并[1,2-a]吡啶。我们的研究发现了许多高效和选择性的 STAT3 抑制剂，例如具有 2-苯基咪唑并[1,2-a]吡啶特权结构的化合物39，它选择性地抑制 STAT3 的磷酸化并抑制随后的信号通路. 而且，39抑制人三阴性乳腺癌 (TNBC) 细胞系的细胞生长、迁移和侵袭。一致地，它在小鼠的细胞系来源和患者来源的异种移植肿瘤模型中实现了显着且剂量依赖性的肿瘤生长抑制。这些结果清楚地表明39是一种高效且选择性的 STAT3 抑制剂。
• Imidazo[1,2-a]pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：EP1803722A1

  公开（公告）日：2007-07-04

  The invention provides novel imidazo[1,2-a]pyridin-3-yl-acetic acid hydrazides of formula (I) wherein R1, R2 and R3 have different meanings, and pharmaceutically acceptable salts, polymorphs, hydrates, tautomers, solvates and stereoisomers thereof. Compounds of formula (I) are useful for treating or preventing diseases associated with GABAA receptors modulation, anxiety, epilepsy, sleep disorders including insomnia, and for inducing sedation-hypnosis, anesthesia, sleep and muscle relaxation. The invention also provides synthetic procedures for preparing said compounds and certain intermediate compounds thereof.

  这项发明提供了式(I)的新型咪唑[1,2-a]吡啶-3-基乙酸腙，其中R1、R2和R3具有不同的含义，以及其药学上可接受的盐、多型体、水合物、互变异构体、溶剂合物和立体异构体。式(I)的化合物对治疗或预防与GABAA受体调节、焦虑、癫痫、包括失眠在内的睡眠障碍以及诱导镇静-催眠、麻醉、睡眠和肌肉松弛相关的疾病有用。该发明还提供了用于制备所述化合物及其某些中间化合物的合成方法。
• A highly selective decarboxylative deuteration of carboxylic acids
  作者：Nian Li、Yunyun Ning、Xiaopeng Wu、Jin Xie、Weipeng Li、Chengjian Zhu

  DOI：10.1039/d1sc00528f

  日期：——

  A scalable, practical and general method for precise deuteration of aliphatic carboxylic acids via synergistic photoredox and HAT catalysis has been developed. The use of recirculation reactor achieved the preparative scale deuteration.

  一种可扩展、实用且通用的精确脂肪族羧酸氘代反应方法已经开发出来，通过光氧化还原和氢原子转移催化的协同作用。利用循环反应器实现了制备规模的氘代反应。
• PROCESS FOR PREPARING ZOLPIDEM
  申请人：Padi Reddy Pratap

  公开号：US20070027180A1

  公开（公告）日：2007-02-01

  A process for preparing zolpidem.

  制备唑吡坦的过程。
• Fast Carbon Isotope Exchange of Carboxylic Acids Enabled by Organic Photoredox Catalysis
  作者：Duanyang Kong、Maxime Munch、Qiqige Qiqige、Christopher J. C. Cooze、Benjamin H. Rotstein、Rylan J. Lundgren

  DOI：10.1021/jacs.0c12819

  日期：2021.2.10

  Carbazole/cyanobenzene photocatalysts promote the direct isotopic carboxylate exchange of C(sp3) acids with labeled CO2. Substrates that are not compatible with transition-metal-catalyzed degradation–reconstruction approaches or prone to thermally induced reversible decarboxylation undergo isotopic incorporation at room temperature in short reaction times. The radiolabeling of drug molecules and precursors

  咔唑/氰基苯光催化剂促进带有标记CO 2的C（sp 3）酸的直接同位素羧酸交换。与过渡金属催化的降解-重建方法不兼容或易于发生热诱导的可逆脱羧作用的底物在室温下会在短时间内经历同位素掺入。证明了用[ 11 C] CO 2对药物分子和前体进行放射性标记。