4-氟-3-(2-羟基乙基氨甲酰基)苯基硼酸 | 874219-25-7

• 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: 4-氟-3-(2-羟基乙基氨甲酰基)苯基硼酸
• 中文别名: 4-氟-3-(2-羟基乙基氨甲酰基)苯硼酸
• 英文名称: 4-fluoro-3-(2-hydroxyethylaminoformyl)phenylboronic acid
• 英文别名: 4-fluoro-3-(2-hydroxyethylcarbamoyl)phenylboronic acid；(4-Fluoro-3-((2-hydroxyethyl)carbamoyl)phenyl)boronic acid；[4-fluoro-3-(2-hydroxyethylcarbamoyl)phenyl]boronic acid
• CAS: 874219-25-7
• 化学式: C₉H₁₁BFNO₄
• mdl: MFCD08235044
• 分子量: 227.0
• InChiKey: AGNPGTVSVSPBEX-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2931900090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Fluoro-3-(2-hydroxyethylcarbamoyl)phenylboronic acid
Product Name:
Synonyms: N-2-Hydroxyethyl 5-borono-2-fluorobenzamide

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
4-Fluoro-3-(2-hydroxyethylcarbamoyl)phenylboronic acid
Ingredient name:
CAS number: 874219-25-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.

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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: C9H11BFNO4
Molecular weight: 227.0

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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, hydrogen fluoride.

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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'-amino-6-bromo-1'-methyl-2-phenylspiro[chroman-4,4'-imidazol]-5'(1'H)-one 、 4-氟-3-(2-羟基乙基氨甲酰基)苯基硼酸 在 双三苯基磷二氯化钯 作用下， 以 1,4-二氧六环 、 Dicaesio carbonate 为溶剂， 反应 0.5h， 以to give pure 5-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)-2-fluoro-N-(2-hydroxyethyl)benzamide (3.1 mg, 12%)的产率得到5-(2'-amino-1'-methyl-5'-oxo-2-phenyl-1',5'-dihydrospiro[chroman-4,4'-imidazole]-6-yl)-2-fluoro-N-(2-hydroxyethyl)benzamide
  参考文献：
  名称：

  INHIBITORS OF BETA-SECRETASE

  摘要：

  本发明涉及以下结构式所代表的化合物：或其药学上可接受的盐。还描述了包括结构式（I）所代表的化合物的药物组合物以及使用这些化合物抑制需要此类治疗的受体中的BACE活性的方法。

  公开号：

  US20130317014A1

文献信息

• Inhibitors Of Beta-Secretase
  申请人：Dillard Lawrence W.

  公开号：US20110218192A1

  公开（公告）日：2011-09-08

  The present invention is directed to a compound represented by the following structural formula: or a pharmaceutically acceptable salt thereof. Pharmaceutical composition comprising a compound represented by Structural Formula (I) and method of use of these compound for inhibiting BACE activity in a subject in need of such treatment are also described.

  本发明涉及以下结构式所表示的化合物或其药学上可接受的盐。还描述了包含由结构式（I）所表示的化合物的药物组合物和使用这些化合物抑制需要此类治疗的受体中的BACE活性的方法。
• INHIBITORS OF BETA-SECRETASE
  申请人：Dillard Lawrence W.

  公开号：US20130317014A1

  公开（公告）日：2013-11-28

  The present invention is directed to a compound represented by the following structural formula: or a pharmaceutically acceptable salt thereof. Pharmaceutical composition comprising a compound represented by Structural Formula (I) and method of use of these compound for inhibiting BACE activity in a subject in need of such treatment are also described.

  本发明涉及以下结构式所代表的化合物：或其药学上可接受的盐。还描述了包括结构式（I）所代表的化合物的药物组合物以及使用这些化合物抑制需要此类治疗的受体中的BACE活性的方法。
• ANTIVIRAL COMPOUNDS
  申请人：HOFFMANN-LA ROCHE INC.

  公开号：US20160000760A1

  公开（公告）日：2016-01-07

  The present invention discloses compounds of Formula I: wherein the variables in Formula I are defined as described herein. Also disclosed are pharmaceutical compositions containing such compounds and methods for using the compounds of Formula I in the prevention or treatment of HCV infection.

  本发明公开了I式化合物：其中I式中的变量如本文所述。还公开了包含这种化合物的药物组合物，以及使用I式化合物在预防或治疗HCV感染方面的方法。
• Exploring the chemical space of functionalized [1,2,4]triazolo[4,3-a]quinoxaline-based compounds targeting the bromodomain of BRD9
  作者：Erica Gazzillo、Martina Pierri、Ester Colarusso、Maria Giovanna Chini、Maria Grazia Ferraro、Marialuisa Piccolo、Carlo Irace、Ines Bruno、Giuseppe Bifulco、Stefania Terracciano、Gianluigi Lauro

  DOI：10.1016/j.bioorg.2023.106677

  日期：2023.10

  previously introduced by us, were here employed to evaluate a second generation of compounds, exploring different substitution patterns on the heterocyclic core. Starting from the promising data obtained from our previously identified [1,2,4]triazolo[4,3-a]quinoxaline-based compounds 1–4, the combination of in silico studies, chemical synthesis, biophysical and in vitro assays led to the identification

  在这里，我们报告了一项与基于[1,2,4]三唑并[4,3- a ]喹喔啉的化合物相关的详细构效关系（SAR）研究，该化合物针对含溴结构域蛋白9（BRD9）的读取器模块。我们之前引入的基于 3D 结构的药效团模型在这里用于评估第二代化合物，探索杂环核心上的不同取代模式。从我们之前鉴定的[1,2,4]三唑并[4,3- a ]喹喔啉基化合物1 – 4获得的有希望的数据开始，计算机研究、化学合成、生物物理和体外测定的结合导致鉴定了一组新的衍生物，选择这些衍生物是为了彻底探索溴结构域结合位点的化学空间。更详细地说，对 C-4 位置不同接头的研究强调了胺间隔基对于与蛋白质对应物的结合是必需的，以及 C-1 处的烷基取代基对于增加对 BRD9 的选择性的关键作用。此外，从我们收集的结果分析中推断出氢键供体基团的重要性，氢键供体基团对于锚定 ZA 区域至关重要，并且是与 Ile53 残基相互作用所必需的。
• Discovery of pyrazolo[3,4-d]pyrimidines as novel mitogen-activated protein kinase kinase 3 (MKK3) inhibitors
  作者：Jéssica E. Takarada、Micael R. Cunha、Vitor M. Almeida、Stanley N.S. Vasconcelos、André S. Santiago、Paulo H. Godoi、Anita Salmazo、Priscila Z. Ramos、Angela M. Fala、Lucas R. de Souza、Italo E.P. Da Silva、Mario H. Bengtson、Katlin B. Massirer、Rafael M. Couñago

  DOI：10.1016/j.bmc.2023.117561

  日期：2024.1

  optimization of inhibitors. In this study, we have developed a TR-FRET-based enzymatic assay for the detection of MKK3 activity in vitro and a BRET-based assay to assess ligand binding to this enzyme within intact human cells. These assays were instrumental in identifying hit compounds against MKK3 that share a common chemical scaffold, sourced from a library of bioactive kinase inhibitors. Initial hits

  双特异性蛋白激酶 MKK3 与肿瘤细胞增殖和存活有关，但其在癌症中的确切作用仍不确定。阐明激酶参与疾病生物学的关键一步是鉴定有效的细胞渗透性激酶抑制剂。目前，MKK3 缺乏用于这些目的的专用工具化合物，以及用于轻松筛选、鉴定和优化抑制剂的有效方法。在这项研究中，我们开发了一种基于 TR-FRET 的酶测定法，用于体外检测 MKK3 活性，并开发了一种基于 BRET 的测定法，用于评估完整人体细胞内配体与该酶的结合。这些测定有助于识别针对 MKK3 的命中化合物，这些化合物共享来自生物活性激酶抑制剂库的共同化学支架。随后通过合成新颖的类似物扩大了最初的成功。使用针对 MKK3 同源模型的分子动力学模拟，对所得构效关系 (SAR) 进行了合理化。我们期望我们的发现能够加速新型、有效、选择性和生物活性抑制剂的开发，从而促进 MKK3 在各种癌症中的作用的研究。