6-氯-2-甲基-咪唑并[1,2-A]吡啶-3-羧酸 | 138642-96-3

• 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-2-甲基-咪唑并[1,2-A]吡啶-3-羧酸
• 中文别名: 6-氯-2-甲基咪唑并[1,2-a]吡啶-3-羧酸
• 英文名称: 6-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid
• CAS: 138642-96-3
• 化学式: C₉H₇ClN₂O₂
• mdl: MFCD00269625
• 分子量: 210.62
• InChiKey: PGYYUAYGIWHUJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 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：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Chloro-2-methylimidazo[1,2-a]pyridine-3-carboxylic 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-Chloro-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid
CAS number: 138642-96-3

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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: C9H7ClN2O2
Molecular weight: 210.6

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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-2-甲基-咪唑并[1,2-A]吡啶-3-羧酸 在 盐酸 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 1-羟基苯并三唑 、 sodium ascorbate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (6-chloro-2-methylimidazo-[1,2-a]-pyridin-3-yl)(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)methanone
  参考文献：
  名称：

  咪唑吡啶稠合三唑类似物的合成、抗寄生虫和抗锥虫活性研究

  摘要：

  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

  DOI：

  10.1039/d0ra07881f
• 作为产物：
  描述：

  2-氨基-5-氯吡啶 在 lithium hydroxide 作用下， 生成 6-氯-2-甲基-咪唑并[1,2-A]吡啶-3-羧酸
  参考文献：
  名称：

  N-（2-苯氧基）乙基咪唑并[1,2 - a ]吡啶-3-羧酰胺类新型抗结核药的设计，合成及生物学活性

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2019.06.038

文献信息

• Design, synthesis and biological evaluation of novel 1,2,3-triazole analogues of Imidazo-[1,2-a]-pyridine-3-carboxamide against Mycobacterium tuberculosis
  作者：Adinarayana Nandikolla、Singireddi Srinivasarao、Yogesh Mahadu Khetmalis、Banoth Karan Kumar、Sankaranarayanan Murugesan、Gauri Shetye、Rui Ma、Scott G. Franzblau、Kondapalli Venkata Gowri Chandra Sekhar

  DOI：10.1016/j.tiv.2021.105137

  日期：2021.8

  3-triazole analogues of imidazo-[1,2-a]-pyridine-3-carboxamide were designed and synthesized based on hybridization approach. The structure of the final compounds are characterized using 1HNMR, 13CNMR, LCMS and elemental analyses and are screened in vitro for anti-tubercular activity using low-oxygen recovery assay (LORA) non-replicating and using microplate alamar blue assay (MABA) against replicating

  基于杂交方法设计和合成了 28 种新型 1,2,3-三唑类似物咪唑-[1,2-a]-吡啶-3-甲酰胺。最终化合物的结构使用1 HNMR、13 CNMR、LCMS 和元素分析进行表征，并使用非复制性低氧回收测定 (LORA) 和微孔板阿拉玛蓝测定 (MABA)在体外筛选抗结核活性对抗复制结核分枝杆菌。MIC被确定。由所得结果观察到，(2,7-二甲基咪唑并[1,2- a ]吡啶-3-基)(4-((1-取代苯基-1H-1,2,3-三唑- 4-基)甲基)哌嗪-1-基)甲酮和(6-氯-2-甲基咪唑并[1,2- a]吡啶-3-基)(4-((1-取代苯基-1H-1,2,3-三唑-4-基)甲基)哌嗪-1-基)甲酮，在对位被电子取代的化合物释放组表现出最好的活性（< 34 μg/mL）。其中，(2,7-二甲基咪唑并[1,2- a ]吡啶-3-基)(4-(2-(4-烷基/取代芳基-1H-1,2,3-三唑-1-基)乙基)
• Ligand-free Pd-catalysed decarboxylative arylation of imidazo[1,2-a]pyridine-3-carboxylic acids with aryl bromides
  作者：Uttam B. Karale、Saradhi Kalari、Jala Shivakumar、Vitthal B. Makane、Dattatraya A. Babar、Ritesh P. Thakare、Bathini Nagendra Babu、Sidharth Chopra、Haridas B. Rode

  DOI：10.1039/c6ra12166g

  日期：——

  A facile ligand-free method for Pd(OAc)2 catalysed decarboxylative arylation of imidazo[1,2-a]pyridine-3-carboxylic acids with hetero(aryl) bromides has been developed. This method is applicable to variety of (hetero)aryl bromides as coupling partner....

  已开发出一种简便的无配体方法，用于Pd（OAc）2催化的咪唑并[1,2-a]吡啶-3-羧酸与杂（芳基）溴化物的脱羧芳基化反应。该方法适用于各种（杂）芳基溴化物作为偶联伙伴。
• [DE] CARBOXAMIDE DES INDOLIZINS UND SEINER AZA- UND DIAZADERIVATE<br/>[EN] INDOLIZINE CARBOXAMIDES AND THE AZA AND DIAZA DERIVATIVES THEREOF<br/>[FR] CARBOXAMIDES D'INDOLIZINE ET LEURS AZA- ET DIAZA-DERIVES
  申请人：SANOL ARZNEI SCHWARZ GMBH

  公开号：WO2006015737A1

  公开（公告）日：2006-02-16

  Die vorliegende Erfindung betrifft neurorezeptoraktive Carboxamid-substituierte Indolizin­-Derivate der allgemeinen Formel (I) wobei X eine Gruppe mit der allgemeinen Formel (X1) repräsentiert.

  本发明涉及具有神经受体活性的羧酰胺取代的吲哩啉衍生物，其一般式为（I），其中X代表一种具有一般式（X1）的基团。
• Design, synthesis, and biological evaluation of novel imidazo[ <i>1,2‐a</i> ]pyridinecarboxamides as potent anti‐tuberculosis agents
  作者：Oluseye K. Onajole、Shichun Lun、Young Ju Yun、Damkam Y. Langue、Michelle Jaskula‐Dybka、Adrian Flores、Eriel Frazier、Ashle C. Scurry、Ambernice Zavala、Karen R. Arreola、Bryce Pierzchalski、A. Jean‐Luc Ayitou、William R. Bishai

  DOI：10.1111/cbdd.13739

  日期：2020.12

  Tuberculosis (TB) is a highly infectious disease that has been plaguing the human race for centuries. The emergence of multidrug‐resistant strains of TB has been detrimental to the fight against tuberculosis with very few safe therapeutic options available. As part of an ongoing effort to identify potent anti‐tuberculosis agents, we synthesized and screened a series of novel imidazo[1,2‐a ]pyridinecarboxamide

  结核病 (TB) 是一种高度传染性疾病，几个世纪以来一直困扰着人类。结核病耐多药菌株的出现不利于抗击结核病，可用的安全治疗选择很少。作为鉴定强效抗结核药物的持续努力的一部分，我们合成并筛选了一系列新型咪唑并 [1,2- a ] 吡啶甲酰胺衍生物的抗结核特性。这些化合物是根据已报道的吲哚甲酰胺 (I2C) 和咪唑并[1,2- a ] 吡啶甲酰胺 (IPAs) 的抗结核特性设计的。在本系列中，我们鉴定了化合物15和16对 H37Rv 结核菌株具有优异的抗结核活性（MIC = 0.10–0.19 μM）；针对选定的Mtb临床分离株进一步筛选了这些化合物。化合物15和16对结核的多重耐药 (MDR) 和广泛耐药 (XDR) 菌株显示出优异的活性（MIC 范围：0.05-1.5 μM），并具有优异的选择性指数。此外，对化合物16 的初步 ADME 研究显示出有利的药代动力学特性。
• [EN] HETEROARYL-SUBSTITUTED 2-PYRIDINYLMETHYLAMINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 2-PYRIDINYLMÉTHYLAMINE SUBSTITUÉS PAR HÉTÉROARYLE
  申请人：UNIV FRIEDRICH ALEXANDER ER

  公开号：WO2009060030A1

  公开（公告）日：2009-05-14

  The present disclosure relates to compounds having the general formula (I) wherein Q represents a five membered heteroaryl group. The compoungs are selective 5-HT1 a modulators and are useful for treating several diseases.

  本公开涉及具有通式（I）的化合物，其中Q代表五元杂环芳基基团。这些化合物是选择性5-HT1a调节剂，可用于治疗多种疾病。