6-氮杂吲哚 | 271-29-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 6-氮杂吲哚
• 中文别名: 6-杂氮吲哚；1H-吡咯并[2,3-C]吡啶；1H-吡咯并[2,3-c]吡啶
• 英文名称: 6-azaindole
• 英文别名: 1H-pyrrolo[2,3-c]pyridine；6-Azaindol
• CAS: 271-29-4
• 化学式: C₇H₆N₂
• mdl: MFCD01686899
• 分子量: 118.138
• InChiKey: XLKDJOPOOHHZAN-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137°C
• 沸点：
  295.8±13.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  29339980
• 危险品标志：
  Xi
• WGK Germany：
  3
• 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：
  存放于惰性气体中，避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Azaindole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 6-Azaindole
CAS number: 271-29-4

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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.
Storage: Store in closed vessels, refrigerated.

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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: C7H6N2
Molecular weight: 118.1

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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

制备方法与用途

用途：用于有机合成。

反应信息

• 作为反应物：
  描述：

  6-氮杂吲哚 在 正丁基锂 、 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.84h， 生成 2-甲基-1H-吡咯并[2,3-c]吡啶
  参考文献：
  名称：

  一种烷基取代氮杂吲哚的制备方法

  摘要：

  一种合成装置，其特征在于，包括：四口瓶(1)、阶梯槽(2)、同温槽(3)、输气管(4)、气源(5)、水浴部(6)。还有2(2‑甲基‑1H‑吡咯[2,3‑c]吡啶‑3‑基)乙烷‑1‑胺的制备方法，其利用前述合成装置以进行。其以6‑氮杂吲哚出发，利用上述装置，通过九个步骤和后处理，得到2(2‑甲基‑1H‑吡咯[2,3‑c]吡啶‑3‑基)乙烷‑1‑胺。

  公开号：

  CN114573578A
• 作为产物：
  描述：

  7-氯-6-氮杂吲哚 在 sodium tetrahydroborate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 以70.95%的产率得到6-氮杂吲哚
  参考文献：
  名称：

  新型吲哚和氮杂吲哚（吡咯并吡啶）大麻素（CB）受体激动剂：设计，合成，结构-活性关系，理化性质和生物活性

  摘要：

  报告了一系列新型的大麻素1（CB 1）和大麻素2（CB 2）受体配体的发现，合成和构效关系（SAR）。基于所述aminoalkylindole类大麻素受体激动剂，联苯部分被引入作为新颖的亲脂性的吲哚3-酰基取代基在11 - 16。此外，系绳是与羧酰胺接头取代-3-羰基17 - 20和氮杂吲哚（吡咯并吡啶）核被设计为具有改进的物理化学性质的吲哚生物电子等排在21 - 25。通过这些SAR努力，几个高亲和力CB 1 / CB 2确定了双重大麻素受体配体。吲哚-3-羧酰胺17对CB 1比CB 2受体具有几位数的纳摩尔亲和力和约80倍的选择性。氮杂吲哚显示出显着改善的理化性质（亲脂性；水溶性）。氮杂吲哚21引起有效的大麻素活性。大麻素受体激动剂17和21在大麻素受体调节的神经传递的急性大鼠脑切片模型中有效地调节了兴奋性突触传递。

  DOI：

  10.1016/j.ejmech.2011.08.021
• 作为试剂：
  描述：

  N-(3-chloro-6-nitroisoquinolin-5-yl)acetamide 、 6-氮杂吲哚 在 6-氮杂吲哚 作用下， 以81的产率得到N-(6-Nitro-3-(1H-pyrrolo[2,3-c]pyridin-1-yl)isoquinolin-5-yl)acetamide
  参考文献：
  名称：

  [EN] PYRROLO[2,3-C]PYRIDINES AS IMAGING AGENTS FOR NEUROFIBRILARY TANGLES
  [FR] PYRROLO[2,3-C]PYRIDINES UTILISABLES EN TANT QU'AGENTS D'IMAGERIE POUR LES ENCHEVÊTREMENTS NEUROFIBRILLAIRES

  摘要：

  本发明涉及式(I)的吡咯吡啶化合物或其药学上可接受的盐，可能适用于成像tau聚集体、β-折叠聚集体、β-淀粉样聚集体或α-突触核聚集体，因此有助于在阿尔茨海默病患者中结合和成像tau聚集体。更具体地，本发明涉及使用本发明化合物作为正电子发射断层扫描（PET）成像中的示踪剂，以研究体内脑中的tau沉积物，从而诊断阿尔茨海默病和其他以tau病理学为特征的神经退行性疾病。本发明还涉及一种测量治疗阿尔茨海默病和其他以tau病理学为特征的神经退行性疾病的临床疗效的方法。

  公开号：

  WO2015191506A2

文献信息

• SUBSTITUTED 4-PYRIDONES AND THEIR USE AS INHIBITORS OF NEUTROPHIL ELASTASE ACTIVITY
  申请人：OOST Thorsten

  公开号：US20140057916A1

  公开（公告）日：2014-02-27

  This invention relates to substituted 4-pyridones of formula 1 and their use as inhibitors of neutrophil elastase activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of pulmonary, gastrointestinal and genitourinary diseases, inflammatory diseases of the skin and the eye and other auto-immune and allergic disorders, allograft rejection, and oncological diseases.

  这项发明涉及式1的取代4-吡啶酮及其作为中性粒细胞弹性蛋白酶活性抑制剂的用途，包含这些化合物的药物组合物，以及将其用作治疗和/或预防肺部、胃肠道和泌尿系统疾病、皮肤和眼睛的炎症性疾病以及其他自身免疫和过敏性疾病、移植物排斥反应和肿瘤性疾病的药剂的方法。
• SULFOXIMINE SUBSTITUTED QUINAZOLINES FOR PHARMACEUTICAL COMPOSITIONS
  申请人：BLUM Andreas

  公开号：US20140135309A1

  公开（公告）日：2014-05-15

  This invention relates to novel sulfoximine substituted quinazoline derivatives of formula I wherein Ar, R 1 and R 2 are as defined herein, and their use as MNK1 (MNK1a or MNK1b) and/or MNK2 (MNK2a or MNK2b) kinase inhibitors, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment or amelioration of MNK1 (MNK1a or MNK1b) and/or MNK2 (MNK2a or MNK2b) mediated disorders.

  这项发明涉及公式I的新型磺酰胺取代的喹唑啉衍生物，其中Ar、R1和R2如本文所定义，并且它们作为MNK1（MNK1a或MNK1b）和/或MNK2（MNK2a或MNK2b）激酶抑制剂的用途，含有这些化合物的药物组合物，以及将其用作治疗或改善MNK1（MNK1a或MNK1b）和/或MNK2（MNK2a或MNK2b）介导的疾病的药剂的方法。
• [EN] SULFOXIMINE SUBSTITUTED QUINAZOLINES FOR PHARMACEUTICAL COMPOSITIONS<br/>[FR] QUINAZOLINES SUBSTITUÉES PAR SULFOXIMINE POUR COMPOSITIONS PHARMACEUTIQUES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014072244A1

  公开（公告）日：2014-05-15

  This invention relates to novel sulfoximine substituted quinazoline derivatives of formula (I), wherein Ar, R1 and R2 are as defined in the description and claims, and their use as MNK1 (MNK1a or MNK1b) and/or MNK2 (MNK2a or MNK2b) kinase inhibitors, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment or amelioration of MNK1 (MNK1a or MNK1b) and/or MNK2 (MNK2a or MNK2b) mediated disorders.

  这项发明涉及一种新型的配方(I)的磺酰胺取代喹唑啉衍生物，其中Ar、R1和R2如描述和声明中所定义，并且它们作为MNK1（MNK1a或MNK1b）和/或MNK2（MNK2a或MNK2b）激酶抑制剂的用途，含有这些化合物的药物组合物，以及将其用作治疗或改善MNK1（MNK1a或MNK1b）和/或MNK2（MNK2a或MNK2b）介导的疾病的药剂的方法。
• [EN] AZADECALIN DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DÉRIVÉS D'AZADÉCALINE EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：VIIV HEALTHCARE UK (NO 5) LTD

  公开号：WO2018002848A1

  公开（公告）日：2018-01-04

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, azadecaline derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors, as represented by compounds of Formula (I). These compounds are useful for the treatment of HIV and AIDS.

  具有药物和生物影响特性的化合物，其药物组合物和使用方法已列出。具体来说，提供了具有独特抗病毒活性的阿扎德卡林衍生物，作为HIV成熟抑制剂，如化合物(I)的公式所代表的那样。这些化合物对于治疗HIV和艾滋病是有用的。
• INDANYLOXYDIHYDROBENZOFURANYLACETIC ACIDS
  申请人：ECKHARDT Matthias

  公开号：US20140163025A1

  公开（公告）日：2014-06-12

  The present invention relates to compounds of general formula I, wherein the groups (Het)Ar and R 1 are defined as in claim 1 , which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及一般式I的化合物， 其中基团(Het)Ar和R1如权利要求1所定义， 具有有价值的药理特性，特别是结合GPR40受体并调节其活性。这些化合物适用于治疗和预防可以受到该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。

表征谱图