(9ci)-1H-苯并咪唑-2-羧酰胺 | 5805-52-7

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9ci)-1H-苯并咪唑-2-羧酰胺
• 中文别名: 1H-苯并咪唑-2-甲酰胺
• 英文名称: 1H-benzo[d]imidazole-2-carboxamide
• 英文别名: 1H-benzimidazole-2-carboxamide；benzimidazole-2-carboxamide；benzimidazole-2-carboximide；2-carbamoylbenzimidazole；1H-benzoimidazole-2-carboxylic acid amide；1H-benzimidazole-2-carboxylic acid amide
• CAS: 5805-52-7
• 化学式: C₈H₇N₃O
• 分子量: 161.163
• InChiKey: XIZCDQOKKYYCRH-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  417.6±28.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P273
• 危险性描述：
  H302,H412
• 储存条件：
  室温和干燥环境中使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1H-Benzimidazole-2-carboxamide
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: 1H-Benzimidazole-2-carboxamide
CAS number: 5805-52-7

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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, refrigerated.
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: C8H7N3O
Molecular weight: 161.2

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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

1H-苯并咪唑-2-甲酰胺是一种医药中间体，可用于制备Pin1抑制剂，如1,2-二取代苯并咪唑衍生物——2-[1-[3-氧代-(3-苯胺基)丙基]-1H-苯并咪唑-2-基]噻唑-4-甲酸。

制备

1H-苯并咪唑-2-甲酰胺是通过三步反应从邻苯二胺和乙醇酸合成得到的一种酰胺类有机物。

反应信息

• 作为反应物：
  描述：

  (9ci)-1H-苯并咪唑-2-羧酰胺 在 potassium carbonate 、 二甲基亚砜 作用下， 以 水 、 硝基苯 为溶剂， 反应 4.0h， 生成 N,N'-二甲基苯并咪唑鎓碘化物
  参考文献：
  名称：

  Glowczyk, Joanna; Serafin, Barbara, Polish Journal of Chemistry, 1984, vol. 58, # 1-3, p. 149 - 156

  摘要：

  DOI：
• 作为产物：
  描述：

  1H-苯并咪唑-2-甲酰氯 在 ammonium hydroxide 作用下， 反应 5.0h， 生成 (9ci)-1H-苯并咪唑-2-羧酰胺
  参考文献：
  名称：

  Structure-Based Design of Novel Benzimidazole Derivatives as Pin1 Inhibitors

  摘要：

  肽丙烯酰基脯氨酸顺反异构酶Pin1在肿瘤发生过程中扮演着关键角色，能够放大和转导多个致癌信号通路。阻断Pin1提供了一种独特的方式来破坏多个致癌通路并诱导细胞凋亡。为了开发有效的Pin1抑制剂，设计并合成了一系列苯并咪唑衍生物。在这些衍生物中，化合物6h和13g表现出最强的Pin1抑制活性，IC50值分别为0.64和0.37μM。体外抗增殖实验表明，化合物6d、6g、6h、6n、6o和7c对人前列腺癌PC-3细胞表现出中等的抗增殖活性。综合来看，这些独特的苯并咪唑衍生物展示出很大的潜力，可以进一步作为有效的Pin1抑制剂进行深入研究，提高其效力。

  DOI：

  10.3390/molecules24071198

文献信息

• [EN] SUBSTITUTED N-HETEROCYCLIC CARBOXAMIDES AS ACID CERAMIDASE INHIBITORS AND THEIR USE AS MEDICAMENTS<br/>[FR] CARBOXAMIDES N-HÉTÉROCYCLIQUES SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE LA CÉRAMIDASE ACIDE ET LEUR UTILISATION EN TANT QUE MÉDICAMENTS
  申请人：BIAL BIOTECH INVEST INC

  公开号：WO2021055627A1

  公开（公告）日：2021-03-25

  The invention provides substituted N-heterocyclic carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

  这项发明提供了替代的N-杂环羧酰胺和相关化合物，含有这些化合物的组合物，医疗工具包，以及使用这些化合物和组合物治疗患者的医疗疾病（例如癌症、溶酶体贮积症、神经退行性疾病、炎症性疾病）的方法。
• [EN] AMINE-LINKED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION<br/>[FR] DÉGRONIMÈRES DE C3-GLUTARIMIDE LIÉS À UNE AMINE POUR LA DÉGRADATION DE PROTÉINES CIBLES
  申请人：C4 THERAPEUTICS INC

  公开号：WO2017197051A1

  公开（公告）日：2017-11-16

  This invention provides amine-linked C3-glutarimide Degronimers and Degrons for therapeutic applications as described further herein, and methods of use and compositions thereof as well as methods for their preparation.

  这项发明提供了胺连接的C3-戊二酰亚胺Degronimers和Degrons，用于治疗应用，如本文进一步描述的，以及它们的使用方法、组合物以及它们的制备方法。
• [EN] DIPEPTIDE AND TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE DIPEPTIDE ET DE TRIPEPTIDE ÉPOXY CÉTONE PROTÉASES
  申请人：ONYX THERAPEUTICS INC

  公开号：WO2014152127A1

  公开（公告）日：2014-09-25

  Provided herein are dipeptide and tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of proliferative diseases including cancer and autoimmune diseases.

  本文提供了二肽和三肽环氧酮蛋白酶抑制剂，其制备方法，相关的药物组合物，以及使用它们的方法。例如，本文提供了化合物的化学式（X）：及其药用盐和包括这些化合物的组合物。本文提供的化合物和组合物可以用于治疗增生性疾病，包括癌症和自身免疫疾病。
• [EN] TRIAZOLE AGONISTS OF THE APJ RECEPTOR<br/>[FR] TRIAZOLES AGONISTES DU RÉCEPTEUR APJ
  申请人：AMGEN INC

  公开号：WO2016187308A1

  公开（公告）日：2016-11-24

  Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures where the definitions of the variables are provided herein.

  公式I和公式II的化合物，其药用盐，上述任何一种的立体异构体，或它们的混合物是APJ受体的激动剂，并可用于治疗心血管和其他疾病。公式I和公式II的化合物具有以下结构，其中变量的定义在此提供。
• [EN] TRIAZOLE PHENYL COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR<br/>[FR] COMPOSÉS PHÉNYLE TRIAZOLE EN TANT QU'AGONISTES DU RÉCEPTEUR APJ
  申请人：AMGEN INC

  公开号：WO2018093579A1

  公开（公告）日：2018-05-24

  Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: (I), (II) where the definitions of the variables are provided herein.

  公式I和公式II的化合物，其药用盐，上述任何一个的立体异构体，或它们的混合物是APJ受体的激动剂，可能用于治疗心血管和其他疾病。公式I和公式II的化合物具有以下结构：(I)，(II)，其中变量的定义在此提供。