2-(2,5-二甲基-1H-吡咯-1-基)苯胺 | 2405-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-(2,5-二甲基-1H-吡咯-1-基)苯胺
• 英文名称: 2-(2,5-dimethyl-1H-pyrrol-1-yl)aniline
• 英文别名: 2-(2,5-dimethyl-1H-pyrrol-1-yl)benzenamine；2-(2,5-dimethylpyrrol-1-yl)aniline
• CAS: 2405-01-8
• 化学式: C₁₂H₁₄N₂
• mdl: MFCD01860278
• 分子量: 186.257
• InChiKey: ZCCGWYQXOIOJRO-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(2,5-Dimethylpyrrol-1-yl)aniline
Synonyms: N-(2-Aminophenyl)-2,5-dimethylpyrrole

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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: 2-(2,5-Dimethylpyrrol-1-yl)aniline
CAS number: 2405-01-8

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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: C12H14N2
Molecular weight: 186.3

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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：

  2-(2,5-二甲基-1H-吡咯-1-基)苯胺 、 2-苯基丁酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl)-2-phenylbutanamide
  参考文献：
  名称：

  Discovery of a Series of 2-Phenyl-N-(2-(pyrrolidin-1-yl)phenyl)acetamides as Novel Molecular Switches that Modulate Modes of K_v7.2 (KCNQ2) Channel Pharmacology: Identification of (S)-2-Phenyl-N-(2-(pyrrolidin-1-yl)phenyl)butanamide (ML252) as a Potent, Brain Penetrant K_v7.2 Channel Inhibitor

  摘要：

  A potent and selective inhibitor of KCNQ2, (S)-5 (ML252, IC50 = 69 nM), was discovered after a high-throughput screen of the MLPCN library was performed. SAR studies revealed a small structural change (ethyl group to hydrogen) caused a functional shift from antagonist to agonist activity (37, EC50 = 170 nM), suggesting an interaction at a critical site for controlling gating of KCNQ2 channels.

  DOI：

  10.1021/jm300700v
• 作为产物：
  描述：

  2,5-己二酮 、 2-硝基苯胺 在 tin(II) chloride dihdyrate 作用下， 以 水 为溶剂， 反应 1.0h， 以70%的产率得到2-(2,5-二甲基-1H-吡咯-1-基)苯胺
  参考文献：
  名称：

  SnCl2 Catalyzed Direct Synthesis of Pyrroles under Aqueous Conditions

  摘要：

  合成取代吡咯与有趣的生物活性有关，但在药物发现领域仍未得到充分探索。近年来，人们对能够提供结构新颖的吡咯的合成方法越来越感兴趣，以便更全面地研究这一化合物类的生物用途。在这里，描述了一种高效且多功能的吡咯实用方案，使用二水合氯化亚锡(II)作为催化剂，在55摄氏度的水性条件下，产率高。此外，这种方法适用于制备多样性和定向的吡咯衍生物。

  DOI：

  10.14233/ajchem.2020.22454

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Synthesis of two distinct pyrrole moiety-containing arenes from nitroanilines using Paal–Knorr followed by an indium-mediated reaction
  作者：Byeong Hyo Kim、Seolhee Bae、Ahra Go、Hyunseung Lee、Cheoloh Gong、Byung Min Lee

  DOI：10.1039/c5ob02101d

  日期：——

  Synthesis of arenes substituted with two different substituted-pyrrole moieties was investigated.

  芳烃合成中探讨了含有两种不同取代吡咯基团的芳烃。
• MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS
  申请人：Sheth Urvi

  公开号：US20120309758A1

  公开（公告）日：2012-12-06

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及调节ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节蛋白，以及相关的组合物和方法。本发明还涉及使用这些调节剂治疗ABC转运蛋白介导的疾病的方法。
• Synthesis, antimycobacterial screening and ligand-based molecular docking studies on novel pyrrole derivatives bearing pyrazoline, isoxazole and phenyl thiourea moieties
  作者：Shrinivas D. Joshi、Sheshagiri R. Dixit、M.N. Kirankumar、Tejraj M. Aminabhavi、K.V.S.N. Raju、Ramanuj Narayan、Christian Lherbet、Kap Seung Yang

  DOI：10.1016/j.ejmech.2015.10.047

  日期：2016.1

  ENR performed using Surflex-Dock in Sybyl-X 2.0 software indicates the occupation of substituted pyrrolyl derivatives into hydrophobic pocket of InhA enzyme. Compounds 9b and 9d exhibited the highest antitubercular activity almost close to isoniazid (0.4 μg/mL) with a MIC value of 0.8 μg/mL. All other compounds showed the good activity with a MIC value of 6.25-100 μg/mL. The compounds were further tested

  我们在这里报告了61个带有吡唑啉，异恶唑和苯基硫脲部分的新型吡咯基衍生物的合成，抗菌和抗结核评估。使用Surflex-Dock对结核分枝杆菌的烯酰ACP还原酶进行了分子对接，Surflex-Dock是参与结核分枝杆菌II型脂肪酸生物合成途径的关键酶之一，这是设计新型抗结核药的有吸引力的靶标。使用Sybyl-X 2.0软件中的Surflex-Dock对ENR的晶体结构进行对接分析，表明取代的吡咯基衍生物已进入InhA酶的疏水口袋中。化合物9b和9d表现出最高的抗结核活性，几乎接近异烟肼（0.4μg/ mL），MIC值为0.8μg/ mL。所有其他化合物均显示出良好的活性，MIC值为6.25-100μg/ mL。使用人肺癌细胞系（A549）对化合物的哺乳动物细胞毒性进行了进一步测试，并且该化合物无毒。一些化合物表现出对InhA的抑制活性。
• Bio-based Material as Medium, Mild and Reusable Catalyst for Paal– Knorr Pyrrole Synthesis with and Without Ultrasonic Irradiation
  作者：Abha Sharma、Illa Siva Kalyani、Anam Fatima

  DOI：10.2174/1570178614666170711145253

  日期：2018.2.7

  a simple, mild and speedy synthesis of N-substituted 2,5-dimethyl pyrrole derivatives in ‘’GAAS’’ as medium and catalyst at room temperature and under ultrasound irradiation. Results: This protocol was employed for the synthesis of various 2,5-dimethyl-N-substituted pyrrolederivatives using both aliphatic as well as aromatic amines in short time (2 to 10 minutes)with excellent yield (84-95%) at room

  背景：吡咯部分存在于天然存在的化合物（例如叶绿素，血红素和维生素B12）中，并存在于多种药物中，例如阿托伐他汀，酮咯酸，伊洛吡唑，托美汀和舒尼替尼。已经使用了多种方法来合成吡咯衍生物。然而，仍然需要环境友好和经济的协议。 方法：我们报道了在“ GAAS”中在室温和超声辐射下简单，温和，快速地合成N-取代的2,5-二甲基吡咯衍生物作为介质和催化剂。 结果：该方案用于在短时间（2至10分钟）内同时使用脂肪族和芳香族胺在室温下以优异的收率（84-95％）合成各种2,5-二甲基-N-取代的吡咯烷衍生物并在超声波照射下。催化系统“ GAAS”已有效再生并重复使用了五次，而活性并未受到重大影响。 结论：总之，我们已经开发出一种环保，简单，快速，可重复使用，温和有效的方法，用于合成N-取代的吡咯衍生物。这种基于生物的方案是一种具有成本效益的绿色方法，可用于合成具有生物活性的N-取代的吡咯衍生物。