1-(4-硝基苯)咪唑 | 18994-90-6

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 1-(4-硝基苯)咪唑
• 中文别名: 1-(4-硝基苄基)咪唑；1-(4-硝基苄基)-1H-咪唑
• 英文名称: 1-(4-nitrobenzyl)-1H-imidazole
• 英文别名: 4-(1-Imidazolylmethyl)-1-nitrobenzene；1-[(4-nitrophenyl)methyl]imidazole
• CAS: 18994-90-6
• 化学式: C₁₀H₉N₃O₂
• mdl: MFCD01799096
• 分子量: 203.2
• InChiKey: FLYGQJXMRPZYHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P273,P305+P351+P338
• 危险性描述：
  H315,H319,H335,H412
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(4-Nitrobenzyl)-1h-imidazole
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: 1-(4-Nitrobenzyl)-1h-imidazole
CAS number: 18994-90-6

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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: C10H9N3O2
Molecular weight: 203.2

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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

反应信息

• 作为反应物：
  描述：

  1-(4-硝基苯)咪唑 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 生成 1-(4-氨基苄基)咪唑
  参考文献：
  名称：

  基于结构的药物设计和合成新型 N-Aryl-2,4-联噻唑-2-胺 CYP1B1 选择性抑制剂克服 A549 细胞的紫杉醇耐药性

  摘要：

  作为一个有前途的癌症治疗靶点，CYP1B1 在紫杉醇耐药的 A549 细胞中过表达；然而，其在耐药性中的作用仍不清楚。生物信息学分析数据表明，CYP1B1与AKT/ERK1/2和粘着斑通路密切相关，从而在紫杉醇耐药和癌症迁移/侵袭中发挥重要作用。沿着类似的思路，AhR 激动剂 7,12-二甲基苯并[ a ]蒽 (DMBA) 增强了紫杉醇抗性并促进了可能源于 CYP1B1 上调的 A549 和 H460 细胞的迁移/侵袭。此外，还设计合成了 83 种新型N -芳基-2,4-联噻唑-2-胺 CYP1B1 选择性抑制剂，以验证 CYP1B1 在紫杉醇抗性 A549 细胞中的作用。令人印象深刻的是，最有效和最具选择性的一个，即77显着抑制 AKT/ERK1/2 和 FAK/SRC 通路，从而逆转紫杉醇抗性并抑制 A549/紫杉醇细胞的迁移和侵袭。总的来说，这项研究不仅展示了 CYP1B1 在紫杉醇

  DOI：

  10.1021/acs.jmedchem.2c01306
• 作为产物：
  描述：

  咪唑 以85%的产率得到
  参考文献：
  名称：

  SCALZO M.; BIAVA M.; CERRETO F.; PORRETTA G. C.; PANICO S.; SIMONETTI N.;+, FARMACO. ED. SCI., 41,(1986) N 4, 392-397

  摘要：

  DOI：

文献信息

• 2-[1H-Benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides as kinase inhibitors
  申请人：Aurrecoechea Natalia

  公开号：US20100081653A1

  公开（公告）日：2010-04-01

  2-[1H-benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and their salts are kinase inhibitors, useful in the treatment of cancer.

  2-[1H-苯并咪唑-2(3H)-基]-2-(嘧啶-2-基)乙酰胺和2-[苯并噻唑-2(3H)-基]-2-(嘧啶-2-基)乙酰胺及其盐是激酶抑制剂，在癌症治疗中有用。
• Synthesis and Serotonergic Activity of N,N-Dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and Analogs: Potent Agonists for 5-HT1D Receptors
  作者：Leslie J. Street、Raymond Baker、William B. Davey、Alexander R. Guiblin、Richard A. Jelley、Austin J. Reeve、Helen Routledge、Francine Sternfeld、Alan P. Watt

  DOI：10.1021/jm00010a025

  日期：1995.5

  or 1). Substitution of the azole ring has been explored either alpha or beta to the point of attachment to indole. In a series of N-linked azoles (X = N), simple unsubstituted compounds have high affinity and selectivity for 5-HT1D receptors. It is proposed that for good affinity and selectivity a hydrogen bond acceptor interaction with the 5-HT1D receptor, through a beta-nitrogen in the azole ring,

  描述了在5-位被咪唑，三唑或四唑环取代的一系列新的N，N-二甲基色胺的合成和5-HT受体活性。这项工作的目的是确定具有高口服生物利用度和低中枢神经系统穿透力的有效和选择性5-HT1D受体激动剂。已经制备了其中唑环通过氮或碳连接到吲哚的化合物。已经研究了共轭和亚甲基桥连的衍生物（n = 0或1）。已经研究了将α-环或β-环取代成吲哚的连接点。在一系列的N-连接的唑类（X = N）中，简单的未取代化合物对5-HT1D受体具有高亲和力和选择性。提出为了获得良好的亲和力和选择性，需要通过唑环中的β-氮与5-HT1D受体的氢键受体相互作用。在一系列的C连接的三唑和四唑（X = C）中，当唑环在1位上被甲基或乙基取代时，观察到对5-HT1D受体的最佳亲和性和选择性。这项研究导致发现1,2,4-三唑10a（MK-462）作为有效的选择性5-HT1D受体激动剂，具有较高的口服生物利用度和快速的口服吸收能力
• INHIBITION OF P38 KINASE ACTIVITY USING SUBSTITUTED HETEROCYCLIC UREAS
  申请人：Dumas Jacques

  公开号：US20120046290A1

  公开（公告）日：2012-02-23

  This invention relates to the use of a group of aryl ureas in treating cytokine mediated diseases, other than cancer and proteolytic enzyme mediated diseases, other than cancer, and pharmaceutical compositions for use in such therapy.

  本发明涉及一组芳香脲在治疗细胞因子介导的疾病（除癌症外）和蛋白水解酶介导的疾病（除癌症外）中的用途，以及用于此类治疗的药物组合物。
• Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas
  申请人：Miller Scott

  公开号：US20080269265A1

  公开（公告）日：2008-10-30

  This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

  这项发明涉及使用一组芳基脲类化合物治疗raf介导的疾病，以及用于该疗法的药物组合物。
• Small “Yaw” Angles, Large “Bite” Angles and an Electron-Rich Metal: Revealing a Stereoelectronic Synergy To Enhance Hydride-Transfer Activity
  作者：Shrivats Semwal、Indulekha Mukkatt、Ranjeesh Thenarukandiyil、Joyanta Choudhury

  DOI：10.1002/chem.201702173

  日期：2017.9.21

  Cyclometalated complexes are an important class of (pre)catalysts in many reactions including hydride transfer. The ring size of such complexes could therefore be a relevant aspect to consider while modulating their catalytic activity. However, any correlation between the cyclometalating ring size and the catalytic activity should be drawn by careful assessment of the pertinent geometrical parameters, and overall

  在包括氢化物转移在内的许多反应中，环金属化的络合物是重要的一类（预）催化剂。因此，在调节其催化活性时，此类配合物的环大小可能是要考虑的相关方面。然而，应通过仔细评估相关的几何参数及其总体电子效应来得出环金属化环尺寸与催化活性之间的任何相关性。在这项研究中，我们研究了五类和六类循环的两类环状环复合物的关键立体电子功能在控制模型氢化物转移反应中的催化效率方面的重要作用。我们的调查表明，在所有相关的立体电子因素（偏航角，咬合角，以及配体和金属中心的电子特性，这些特性决定了催化过程中配合物的氢化物供体能力（亲水性）。因此，发现具有小的偏航角和大的咬合角，强的给体配体和富电子的金属的六元螯合物比其五元类似物是更好的催化剂。前沿的分子轨道分析支持了上述与螯合环相关的立体电子协同效应在控制配合物氢化物供体能力方面的重要作用。现已发现，富电子和富电子金属比其五元类似物是更好的催化剂。前沿的分子轨道分析支持