4-(咪唑并[1,2-a]吡啶-2-基)苯胺 | 139705-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(咪唑并[1,2-a]吡啶-2-基)苯胺
• 中文别名: 4-咪唑并[1,2-a]吡啶-2-苯胺
• 英文名称: 4-(imidazo[1,2-a]pyridin-2-yl)aniline
• 英文别名: 2-(4-aminophenyl)imidazo[1,2-a]pyridine；4-imidazo[1,2-a]pyridin-2-ylaniline
• CAS: 139705-74-1
• 化学式: C₁₃H₁₁N₃
• mdl: MFCD00107394
• 分子量: 209.25
• InChiKey: FPCHINCJTRAFAK-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206°
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险类别：
  IRRITANT

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Imidazo[1,2-a]pyridin-2-ylaniline
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.
4-Imidazo[1,2-a]pyridin-2-ylaniline
Ingredient name:
CAS number: 139705-74-1

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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.

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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: C13H11N3
Molecular weight: 209.3

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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：

  4-(咪唑并[1,2-a]吡啶-2-基)苯胺 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-(4′-dimethylaminophenyl)-6-imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Structure−Activity Relationship of Imidazo[1,2-a]pyridines as Ligands for Detecting β-Amyloid Plaques in the Brain

  摘要：

  A series of novel beta-amyloid (Abeta) aggregate-specific ligands, 2-(4'-dimethylaminophenyl)-6-iodoimidazo[1,2-alpha]pyridine, (IMPY), and its related derivatives were prepared. An in vitro binding study with preformed Abeta aggregates showed that 16(IMPY) and its bromo derivative competed with binding of 2-(4'-dimethylaminophenyl)-6-iodobenzothiazole, [I-125]7(TZDM), a known ligand for Abeta aggregates, with high binding affinities (K-i = 15 and 10 nM, respectively). In vitro autoradiography of brain sections of a transgenic mouse (Tg2576) with [I-125]16(IMPY) displayed high selective binding to amyloid-like structures, comparable to that observed by staining with thioflavin-S visualized under fluorescence. In vivo biodistribution after an intravenous injection of [I-125]16(IMPY) in normal mice showed a high initial brain uptake and fast washout, indicating a low background activity associated with this iodinated ligand. Taken together, the data suggests that [I-123]16(IMPY) may be useful for imaging Abeta aggregates in patients with Alzheimer's disease.

  DOI：

  10.1021/jm020351j
• 作为产物：
  描述：

  2-溴-4'-硝基苯乙酮 在 sodium sulfide 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 54.0h， 生成 4-(咪唑并[1,2-a]吡啶-2-基)苯胺
  参考文献：
  名称：

  Substituent Effects on Fluorescent Properties of Imidazo[1,2-a]pyridine-Based Compounds

  摘要：

  为了寻找新型荧光有机化合物，合成了20种咪唑并[1,2-a]吡啶(1)的衍生物，并研究了它们的荧光性质。尽管母体化合物1在室温下为液态(λfl = 370.5 nm，Φ = 0.57，在乙醇中)，但2-苯基咪唑并[1,2-a]吡啶(5)、2-(2-萘基)咪唑并[1,2-a]吡啶(16)、7-甲基咪唑并[1,2-a]吡啶(3)、7-甲基-2-苯基咪唑并[1,2-a]吡啶(12)和7-甲基-2-(2-萘基)咪唑并[1,2-a]吡啶(17)被发现能形成热稳定的固态化合物(熔点55-190°C)，且对母体化合物的荧光性质影响不大(λfl = 374-381 nm，Φ = 0.50-0.78，在乙醇中)。在4'-取代的2-苯基衍生物中，发现引入强电子供体的氨基和二甲氨基(分别为2-(4-氨基苯基)咪唑并[1,2-a]吡啶(7)和2-[4-(二甲氨基)苯基]咪唑并[1,2-a]吡啶(8))会导致它们的荧光显著红移(λfl = 445和446 nm，在乙醇中)，从而提供了调节IP衍生物荧光颜色的途径。7和8荧光的红移归因于激发态分子内电荷转移态的贡献。

  DOI：

  10.1246/bcsj.72.1327

文献信息

• 1-Phenyl-<i>N</i>-(benzothiazol-2-yl)methanimine derivatives as Middle East respiratory syndrome coronavirus inhibitors
  作者：Min-Qi Hu、Heng Li、Ying Lin、Ying Zhang、Jie Tang、Jian-Ping Zuo、Li-Fang Yu、Xian-Kun Tong、Wei Tang、Fan Yang

  DOI：10.1039/d0ra08442e

  日期：——

  A series of novel 1-phenyl-N-(benzothiazol-2-yl)methanimine derivatives were synthesized and their in vitro inhibitory potencies were evaluated on MERS-S pseudovirus.

  一系列新颖的1-苯基-N-(苯并噻唑-2-基)甲醛亚胺衍生物被合成，并在MERS-S假病毒上评估了它们的体外抑制效力。
• HETEROCYCLIC INHIBITORS OF AN Hh-SIGNAL CASCADE, MEDICINAL COMPOSITIONS BASED THEREON AND METHODS FOR TREATING DISEASES CAUSED BY THE ABERRANT ACTIVITY OF AN Hh-SIGNAL SYSTEM
  申请人：Ivaschenko Andrey Alexandrovich

  公开号：US20110053915A1

  公开（公告）日：2011-03-03

  The invention relates to novel heterocyclic compounds and to the use thereof, to pharmaceutical compositions containing said chemical compounds as an active ingredient and to the use thereof for producing medicinal preparations for the human being and warm-blood animals for treating diseases caused by the aberrant activity of an Hedgehog (Hh)-signal system, in particular oncological diseases. The invention also relates to the use of the above-mentioned compounds in the form of ‘molecular pharmacological tools’ for examining (in vitro and in vivo) the biochemical features of the Hh-signal system, in particular, the interaction of Hh protein and transmembrane proteins, namely, suppressor Patched (Ptc) and protooncogenic proteins. The eight groups of the claimed compounds comprise the derivatives of 2,6-dihydro-7H-pyrazolo[3,4-d]pyridazine-7-one and 1,4-dihydropyrazolo[3,4-b][1,4]thiazine-5-one; N-acidylated 4-imidazo[1,2-a]pyrimidine-2-il-anilines; ([4H-thino[3,2-b]pyrrol-5-il) carbonyl]piperidine-4-carbonic acid amides; 2-(4carbomoilpyperidine-1-il)-isonicotinic acid amides; N-sylphonyl-1,2,3,4-tetrahydroquinoline-6-carbonic acid amides; and pyridine 2-amino-4,5,6,7-tetrahydrothieno[2,3-c] N-acidylated 3-azole derivatives.

  该发明涉及新颖的杂环化合物及其用途，包括含有该化合物作为活性成分的药物组合物，以及用于制备用于治疗由Hedgehog（Hh）信号系统异常活性引起的人类和温血动物疾病的药物制剂。该发明还涉及上述化合物的使用形式为“分子药理学工具”，用于检查Hh信号系统的生化特征（体外和体内），特别是Hh蛋白与跨膜蛋白之间的相互作用，即抑制剂Patched（Ptc）和原癌基因蛋白。所述化合物的八个类别包括2,6-二氢-7H-吡唑并[3,4-d]吡啶嗪-7-酮和1,4-二氢吡唑并[3,4-b][1,4]噻嗪-5-酮的衍生物；N-酰化的4-咪唑并[1,2-a]嘧啶-2-基-苯胺；([4H-噻吩[3,2-b]吡咯-5-基)羰基]哌啶-4-羧酸酰胺；2-(4-羧甲基哌啶-1-基)-异尼古丁酸酰胺；N-磺酰基-1,2,3,4-四氢喹啉-6-羧酸酰胺；以及吡啶2-氨基-4,5,6,7-四氢噻吩[2,3-c] N-酰化的3-唑衍生物。
• Preparation of 2-aryl and 2-aryloxymethyl imidazo[1,2-<i>a</i>]pyridines and related compounds
  作者：Richard J. Sundberg、D. J. Dahlhausen、G. Manikumar、B. Mavunkel、Atanu Biswas、V. Srinivasan、Fred King、Philip Waid

  DOI：10.1002/jhet.5570250119

  日期：1988.1

  A series of substituted 2-aryl imidazo[1,2-a]pyridines has been prepared in which a variety of substituents are introduced on the 4′-position of the phenyl ring and on the 3, 5, 6 or 7 position of the heterocyclic ring. Most examples have acetamido, bromo, cyano, or formyl substituents at the 4′-position. Analogous imidazo-[2,1-b]fhiazoles and imidazo[1,2-a]pyrimidines have also been prepared. Another

  一系列取代的2-芳基咪唑并[1,2-α]吡啶已被制备，其中多种取代基被引入在苯环的4'位和在3，5的，6或7位杂环。大多数实例在4'-位具有乙酰氨基，溴，氰基或甲酰基取代基。还已经制备了类似的咪唑并[ 2，1- b ]噻唑和咪唑并[1,2- a ]嘧啶。制备了由咪唑的4'-甲酰基苯氧基甲基衍生物，吡啶，噻唑，苯并咪唑和环取代的咪唑并[1,2- a ]吡啶的三个位置异构体组成的另一系列化合物。还制备了咪唑和咪唑并[1,2- a ]吡啶的2-（4'-甲酰基苯基乙烯基）衍生物。
• リードスルー誘導剤およびその医薬用途
  申请人：京都薬品工業株式会社

  公开号：JP2020100564A

  公开（公告）日：2020-07-02

  【課題】新規なリードスルー誘導剤を提供する。【解決手段】本発明は、一般式（Ｉ）：［式中の各記号は、明細書に記載のとおりである。］で表される化合物またはその医薬上許容される塩、該化合物を有効成分として含有する医薬組成物に関する。本発明によれば、上記化合物がリードスルー活性を有しているため、筋ジストロフィー、デュシェンヌ型筋ジストロフィー、嚢胞性線維症、ムコ多糖症、セロイドリポフスチン症、ニーマンピック病等のナンセンス変異型遺伝子疾患の予防または治療剤として有用な医薬を提供することができる。【選択図】なし

  提供新型的的导入物质。本发明涉及一种包含化合物或其医药上可接受的盐的药物组合物，其由通式（I）表示：［式中的每个符号如说明书所述。］根据本发明，由于上述化合物具有导入活性，因此可以提供用于预防或治疗肌肉萎缩症、杜欧肌萎缩症、囊性纤维症、黏多糖症、瑟罗依-利波斯汀症、尼曼-匹克病等无义突变型遗传疾病的有用药物。【选择图】无
• [EN] CYCLOPENTANECARBOXAMIDE DERIVATIVES, MEDICAMENTS CONTAINING SUCH COMPOUNDS AND THEIR USE<br/>[FR] DÉRIVÉS DE CYCLOPENTANECARBOXAMIDE, MÉDICAMENTS CONTENANT CES COMPOSÉS ET LEUR UTILISATION
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011048018A1

  公开（公告）日：2011-04-28

  The invention relates to cyclopentanecarboxamide derivatives of formula 1, to their use as Fatty Acid Synthase inhibitors, to methods for their therapeutic use and to pharmaceutical compositions containing them, wherein R1, R2, R3, LO, W, AR1, n are as defined in claim 1.

  这项发明涉及公式1的环戊烷羧酰胺衍生物，它们的用途是作为脂肪酸合成酶抑制剂，用于它们的治疗用途的方法，以及含有它们的药物组合物，其中R1、R2、R3、LO、W、AR1、n如权利要求1中所定义。