3-氨基-4-(环己基氨基)苯甲酸甲酯 | 503859-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-4-(环己基氨基)苯甲酸甲酯
• 英文名称: methyl 3-amino-4-(cyclohexylamino)benzoate
• 英文别名: SRS8-61；3-amino-4-cyclohexylamino-benzoic acid methyl ester
• CAS: 503859-27-6
• 化学式: C₁₄H₂₀N₂O₂
• mdl: MFCD13343558
• 分子量: 248.325
• InChiKey: QZHHJKXBIHAXTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922499990

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 3-amino-4-(cyclohexylamino)benzoate
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: Methyl 3-amino-4-(cyclohexylamino)benzoate
CAS number: 503859-27-6

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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: C14H20N2O2
Molecular weight: 248.3

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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：

  3-氨基-4-(环己基氨基)苯甲酸甲酯 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 magnesium sulfate 、 三乙胺 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.34h， 生成 methyl 2-(2-aminopyridin-4-yl)-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Multicomponent Solvent-Free Synthesis Of Benzimidazolyl Imidazo[1,2-a]-pyridine Under Microwave Irradiation

  摘要：

  A novel one-pot, three-component reaction employing variously substituted benzimidazole-linked amino pyridines, aldehydes, and isonitriles catalyzed by scandium(III) triflate under solvent-free conditions were accomplished. This new synthetic methodology facilitates the rapid generation of intricate molecular frameworks in three-dimensional fashion leading to benzinaidazole-imidazo [1,2-a] pyridines. This approach is envisioned as an environmentally benign process and a simple operation to the biological interesting compounds. The present synthetic sequence permits the introduction of three points of structural diversity to expand chemical space with high purity and excellent yields.

  DOI：

  10.1021/co400010y
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 氯化亚砜 、 铁粉 、 potassium carbonate 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 3-氨基-4-(环己基氨基)苯甲酸甲酯
  参考文献：
  名称：

  作为新型改良铁死亡抑制剂的 Ferrostatin-1 甲酰哌嗪类似物的设计、合成和评估

  摘要：

  本研究基于已知的铁死亡抑制剂铁他汀-1（Fer-1）的结构，设计并合成了一系列新型甲酰基哌嗪衍生的铁死亡抑制剂。评估了这些合成化合物在 Erastin 诱导的人脐静脉内皮细胞 (HUVEC) 中的抗铁死亡活性。研究发现，一些新化合物，特别是化合物 ，表现出有效的抗铁死亡活性，其能够恢复细胞活力、减少铁积累、清除活性氧、维持线粒体膜电位、增加 GSH 水平、降低 LPO和 MDA 含量，并上调 GPX4 表达。此外，该化合物表现出比Fer-1更优异的微粒体稳定性。目前的结果表明，该化合物是开发治疗血管疾病的新型铁死亡抑制剂的有前途的先导化合物。

  DOI：

  10.1016/j.bmc.2024.117716

文献信息

• Compounds useful for treating hepatitis C virus
  申请人：——

  公开号：US20030134853A1

  公开（公告）日：2003-07-17

  A series of compounds of Formula I are disclosed which are useful in treating viral hepatitus C. 1

  披露了一系列的I公式化合物，这些化合物在治疗丙型病毒性肝炎方面是有用的。
• [EN] COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING FERROPTOSIS AND TREATING EXCITOTOXIC DISORDERS<br/>[FR] COMPOSÉS, COMPOSITIONS, ET PROCÉDÉS POUR MODULER LA FERROPTOSE ET TRAITER DES TROUBLES EXCITOTOXIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2013152039A1

  公开（公告）日：2013-10-10

  The present invention provides, inter alia, a compound having the structure: (Formula (I). Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, and methods for treating or ameliorating the effects of a neurodegenerative disease.

  本发明提供了一种具有以下结构的化合物：（化学式（I）。还提供了含有药用载体和根据本发明的化合物的组合物。进一步提供了用于治疗或改善受体内兴奋毒性障碍影响的方法，用于调节受体内铁死亡的方法，用于减少细胞内活性氧化物种（ROS）的方法，以及用于治疗或改善神经退行性疾病影响的方法。
• [EN] MODULATING FERROPTOSIS AND TREATING EXCITOTOXIC DISORDERS<br/>[FR] MODULATION DE LA FERROPTOSE ET TRAITEMENT DES TROUBLES EXCITOTOXIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2015084749A1

  公开（公告）日：2015-06-11

  The present invention provides, inter alia, a compound having the structure of Formula (I). Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, and methods for treating or ameliorating the effects of a neurodegenerative disease.

  本发明提供了一种具有式（I）结构的化合物。还提供了含有药用载体和根据本发明的化合物的组合物。此外还提供了用于治疗或改善受体内兴奋毒性障碍影响的方法，用于调节受体内铁死亡的方法，用于减少细胞内活性氧化物种（ROS）的方法，以及用于治疗或改善神经退行性疾病影响的方法。
• A Novel Mechanistic Study on Ultrasound-Assisted, One-Pot Synthesis of Functionalized Benzimidazo[2,1-<i>b</i>]quinazolin-1(1<i>H</i>)-ones
  作者：Li-Hsun Chen、Tsai-Wen Chung、Bharat D. Narhe、Chung-Ming Sun

  DOI：10.1021/acscombsci.5b00186

  日期：2016.3.14

  Ultrasound-assisted synthesis of benzimidazo[2,1-b]quinazolin-1(1H)-ones was achieved via piperidine-catalyzed three-component reaction of 2-aminobenzimidazoles, an aromatic aldehyde, and 1,3-dione in aqueous isopropanol. This mechanism was first suspected following our identification of unusual reaction intermediates in a one-pot reaction. An unprecedented coupling reaction, it involved a nucleophilic

  通过哌啶催化的2-氨基苯并咪唑，芳香族醛和1,3-二酮在异丙醇水溶液中的三组分反应实现苯并咪唑并[2,1 - b ]喹唑啉-1（1 H）-的超声辅助合成。在我们确定了一锅反应中不寻常的反应中间体之后，首先怀疑了这种机制。前所未有的偶联反应，它涉及2-氨基苯并咪唑对原位生成的迈克尔加合物的亲核攻击，然后发生电环形成反应。与普遍接受的机理相反，2-氨基苯并咪唑与Knoevenagel加合物的直接反应不能释放目标化合物。
• Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization
  作者：Po-Hsin Eric Yao、Sunil Kumar、Yu-Li Liu、Chiu-Ping Fang、Chia-Chen Liu、Chung-Ming Sun

  DOI：10.1021/acscombsci.7b00004

  日期：2017.4.10

  Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent yields. In situ intramolecular cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanomethylbenzimidazoles with salicylaldehydes promoted by triethylamine

  N-（2-氨基苯基）-2-氰基乙酰胺通过一锅三步顺序反应以优异的收率实现了香豆素连接的苯并咪唑的多样性导向合成。氰基乙酰胺的原位分子内环化得到苯并咪唑，随后使2-氰基甲基苯并咪唑与三乙胺促进的水杨醛进行Knoevenagel缩合反应以达到目标化合物。的重要中间体，2-（2-亚氨基-2- ħ -苯并吡喃-3-基）-1 ħ -苯并咪唑用X射线分析，并进一步水解为2-（香豆素-3-基）苯并咪唑在酸性条件下。在合成的化合物中，发现有一些是猪肾d-氨基酸氧化酶（pk DAO）。