2,7-二甲基咪唑并[1,2-a]吡啶-3-羧酸乙酯 | 81448-48-8

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 2,7-二甲基咪唑并[1,2-a]吡啶-3-羧酸乙酯
• 中文别名: 乙基2,8-二甲基咪唑并[1,2-a]吡啶-3-羧酸酯；2,7-二甲基咪唑并[1,2-A]吡啶-3-羧酸乙酯；2,7-二甲基-1H-咪唑并[1,2-a]吡啶-3-甲酸乙酯
• 英文名称: ethyl 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxylate
• CAS: 81448-48-8
• 化学式: C₁₂H₁₄N₂O₂
• mdl: MFCD00139510
• 分子量: 218.255
• InChiKey: CQNUHMHESISBRX-UHFFFAOYSA-N

物化性质

• 熔点：
  79-82°
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 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,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 2,7-dimethylimidazo[1,2-a]pyridine-3-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 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxylate
CAS number: 81448-48-8

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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: C12H14N2O2
Molecular weight: 218.3

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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：

  2,7-二甲基咪唑并[1,2-a]吡啶-3-羧酸乙酯 在 20 % platinum on carbon 、 palladium 10% on activated carbon 、 氢气 、 重水 作用下， 反应 24.0h， 以52%的产率得到ethyl 2,7-bis(methyl-d3)imidazo[1,2-a]pyridine-3-carboxylate-6,8-d2
  参考文献：
  名称：

  [EN] DEUTERATED IMIDAZOPYRIDINES
  [FR] IMIDAZOPYRIDINES DEUTÉRÉS

  摘要：

  提供了一系列咪唑吡啶和吡唑吡啶化合物，其中碳氢键已被同位素碳-氘键所取代，以及这些化合物的合成、组成和使用方法。各种实施方式提供了杀灭和/或抑制结核分枝杆菌和/或埃维分枝杆菌生长的方法，以及治疗、预防和/或缓解结核分枝杆菌、埃维分枝杆菌或其他分枝杆菌感染（如麻风分枝杆菌或溃疡分枝杆菌）在受试者中的方法。

  公开号：

  WO2019175737A1
• 作为产物：
  描述：

  2-氨基-4-甲基吡啶 、 2-氯乙酰乙酸乙酯 以 乙二醇二甲醚 为溶剂， 反应 48.0h， 以10.93 g的产率得到2,7-二甲基咪唑并[1,2-a]吡啶-3-羧酸乙酯
  参考文献：
  名称：

  哌嗪子-1,3-苯并噻嗪-4-酮（pBTZ）与2,7-二甲基咪唑并[1,2 - a ]吡啶-3-羧酸和7-苯基乙酰头孢菌素的共轭物的设计，合成和抗结核活性

  摘要：

  结核病（TB）仍然是世界上威胁最大的疾病之一，迫切需要开发新疗法。在这里，我们描述了pBTZ与咪唑并吡啶和头孢菌素支架之间的缀合物的设计以及随后的合成和研究的原理。总体而言，在微孔板Alamar Blue（MABA）分析中，某些化合物在2–0.2μM范围内显示出显着的抗TB活性。

  DOI：

  10.1016/j.bmcl.2016.02.076

文献信息

• Design, Synthesis and Antimycobacterial Activity of Novel Imidazo[1,2-a]pyridine Amide-Cinnamamide Hybrids
  作者：Linhu Li、Zhuorong Li、Mingliang Liu、Weiyi Shen、Bin Wang、Huiyuan Guo、Yu Lu

  DOI：10.3390/molecules21010049

  日期：——

  the design and synthesis of a series of novel imidazo[1,2-a]pyridine amide-cinnamamide hybrids linked via an alkyl carbon chain. All 38 new hybrids were evaluated for their antimycobacterial activity against M. tuberculosis (MTB) H37Rv ATCC 27294 using the microplate Alamar Blue assay (MABA). Although the hybrids are less active than the two reference compounds, the promising activity (MICs: 4 μg/mL)

  我们在此报告了一系列通过烷基碳链连接的新型咪唑并[1,2-a]吡啶酰胺-肉桂酰胺杂合物的设计和合成。使用微孔板Alamar Blue分析（MABA）评估了所有38个新杂种对结核分枝杆菌（MTB）H37Rv ATCC 27294的抗分枝杆菌活性。尽管杂种的活性不及两种参考化合物，但2,6-二甲基咪唑并[1,2-a]吡啶酰胺-肉桂酰胺杂种11e和11k的有希望的活性（MIC：4μg/ mL）可能是一个很好的起点进一步寻找抗多药结核病的新的先导化合物。
• Design, synthesis and antimycobacterial activity of novel imidazo[1,2- a ]pyridine-3-carboxamide derivatives
  作者：Kai Lv、Linhu Li、Bo Wang、Mingliang Liu、Bin Wang、Weiyi Shen、Huiyuan Guo、Yu Lu

  DOI：10.1016/j.ejmech.2017.05.044

  日期：2017.9

  report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against

  我们在此报告基于我们实验室中发现的IMB-1402的结构和合成的“新型咪唑并[1,2- a ]吡啶-3-甲酰胺（IPA）”的设计和合成。结果表明，在苯环上具有给电子基团的2,6-二甲基-N- [2-（苯基氨基）乙基] IPAs作为有效的支架。化合物26g和26h对药物敏感/耐药的MTB菌株具有相当大的活​​性（MIC：0.041–2.64μM），并且它们对MTB H37Rv的安全性指标可接受，SI值分别为4395和1405。此外，N- [2-（哌嗪-1-基）乙基]部分也被鉴定为潜在的替代接头（化合物31），为进一步的SAR研究开辟了新的方向。
• Thermal and Microwave-Assisted Rapid Syntheses of Substituted Imidazo[1,2-a]pyridines Under Solvent- and Catalyst-Free Conditions
  作者：Subbarayappa Adimurthy、Kaushik Chunavala、Girdhar Joshi、Eringathodi Suresh

  DOI：10.1055/s-0030-1258405

  日期：2011.2

  microwave-assisted rapid syntheses of highly substituted imidazo[1,2-a]pyridine derivatives by reaction of aminopyridines and α-bromo-β-keto esters under solvent-free conditions are described. Reactions carried out under microwave irradiation give the highest yields of products in reaction times of less than two minutes. aminopyridines - α-bromo-β-keto esters - imidazo[1,2-a]pyridines - microwave irradiation

  描述了在无溶剂条件下通过氨基吡啶与α-溴-β-酮酯的反应进行热取代和微波辅助快速合成高度取代的咪唑并[1,2- a ]吡啶衍生物。在少于两分钟的反应时间内，在微波辐射下进行的反应可获得最高的产物收率。 氨基吡啶-α-溴-β-酮酸酯-咪唑并[1,2- a ]吡啶-微波辐射-无溶剂-热
• Synthesis, study of antileishmanial and antitrypanosomal activity of imidazo pyridine fused triazole analogues
  作者：Adinarayana Nandikolla、Singireddi Srinivasarao、Banoth Karan Kumar、Sankaranarayanan Murugesan、Himanshu Aggarwal、Louise L. Major、Terry K. Smith、Kondapalli Venkata Gowri Chandra Sekhar

  DOI：10.1039/d0ra07881f

  日期：——

  compounds were screened in vitro for antileishmanial and antitrypanosomal activity against Leishmania major and Trypanosoma brucei parasites, respectively. Among the tested analogues, five compounds (8d, 8f, 8j, 10b and 10d) exhibited significant antileishmanial activity while three compounds (10b, 11a and 11b) showed substantial activity against T. brucei parasite. In silico ADME prediction studies depicted

  使用取代的吡啶、炔丙基溴、2-叠氮乙基设计并合成了四组共 35 个化合物的新型 1,2,3-三唑类咪唑-[1,2 - a ]-吡啶-3-甲酰胺类化合物4-甲基苯磺酸盐和取代的乙炔。使用1 H NMR、13 C NMR、LCMS 和元素分析对这些化合物进行了表征，并获得了一种显着活性化合物8f的晶体结构。所有合成和表征的化合物都在体外筛选了抗利什曼原虫和布氏锥虫的抗利什曼原虫和抗锥虫活性寄生虫，分别。在测试的类似物中，五种化合物（8d、8f、8j、10b和10d）表现出显着的杀虫活性，而三种化合物（10b、11a和11b ）表现出对布氏锥虫的显着活性。计算机ADME 预测研究表明，基本化合物遵循 Lipinski 的五法则。计算机预测毒性概况表明测试的化合物是无毒的，这通过对HeLa细胞缺乏细胞毒性而通过实验证实。最后，还对最活跃的抗利什曼虫化合物进行了 10 天的分子对接研究，以研究其在选
• Design, synthesis and biological activity of N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides as new antitubercular agents
  作者：Apeng Wang、Kai Lv、Linhu Li、Hongtao Liu、Zeyu Tao、Bin Wang、Mingliang Liu、Chao Ma、Xican Ma、Bing Han、Aoyu Wang、Yu Lu

  DOI：10.1016/j.ejmech.2019.06.038

  日期：2019.9

  A series of N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides (IPAs), based on the structure of WZY02 discovered in our lab, were designed and synthesized as new anti-TB agents. Results reveal that many of them exhibit excellent in vitro inhibitory activity with low nanomolar MIC values against both drug-sensitive MTB strain H37Rv and drug-resistant clinical isolates. Compounds 15b and 15d display

  根据在我们实验室中发现的WZY02的结构，设计并合成了一系列N-（2-苯氧基）乙基咪唑并[1,2 - a ]吡啶-3-甲酰胺（IPAs），作为新型抗结核药物。结果表明，它们中的许多对药物敏感性MTB菌株H37Rv和耐药性临床分离株均表现出优异的体外抑制活性，且纳摩尔摩尔MIC值低。化合物15b和15d显示出良好的安全性和药代动力学特征，表明它们有望成为未来抗结核药物发现的先导化合物。