4-乙酰氨基甲基苯基硼酸 | 850568-41-1

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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-乙酰氨基甲基苯基硼酸
• 中文别名: 4-乙酰甲基苯硼酸
• 英文名称: (4-(acetamidomethyl)phenyl)boronic acid
• 英文别名: [4-(acetamidomethyl)phenyl]boronic acid
• CAS: 850568-41-1
• 化学式: C₉H₁₂BNO₃
• mdl: MFCD06659818
• 分子量: 193.01
• InChiKey: ZMJVNKSOLIUBKO-UHFFFAOYSA-N

物化性质

• 熔点：
  278-280
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Acetamidomethylphenylboronic acid
Product Name:
Synonyms: 4-Acetylaminomethylphenylboronic acid

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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-Acetamidomethylphenylboronic acid
Ingredient name:
CAS number: 850568-41-1

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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: C9H12BNO3
Molecular weight: 193.0

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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.

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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：

  4-乙酰氨基甲基苯基硼酸 、 4-氯吡咯并[1,2-a]喹喔啉 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以49%的产率得到N-[4-(pyrrolo[1,2-a]quinoxalin-4-yl)benzyl]acetamide
  参考文献：
  名称：

  抑制RAD51的D环活性的候选药物的优化。

  摘要：

  RAD51是同源重组（HR）修复中的中心蛋白，它首先结合ssDNA，然后通过D环中间体催化链入侵。另外，RAD51通过保护停滞的复制叉在忠实的DNA复制中发挥作用。这需要RAD51结合DNA，但可能不需要RAD51的链入侵活性。我们先前描述了一种名为RI（dl）-2的RAD51小分子抑制剂（D-loop形成＃2的RAD51抑制剂，以下称为2 h），它在抑制ssDNA结合的同时抑制了D-loop的活性。然而，2 h在体内抑制HR的能力有限，仅阻止了细胞中总HR事件的约50％。我们试图通过进行结构-活性关系（SAR）运动来获得更强效的2 h类似物，以改善这一点。大多数化合物是由1-（2-氨基苯基）吡咯通过以下方法制得的：通过与醛缩合形成喹喔啉部分，然后将所得的4,5-二氢中间体脱氢，或与N，N'-羰基二咪唑缩合，进行氯化和通过铃木-宫浦联轴器安装4位取代基。许多类似物表现出增强的针对人RAD5

  DOI：

  10.1002/cmdc.201900075
• 作为产物：
  描述：

  4-(aminomethyl)phenylboronic acid hydrochloride 、 乙酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以59 %的产率得到4-乙酰氨基甲基苯基硼酸
  参考文献：
  名称：

  烷基化酰肼作为具有 T 细胞调节特性的高效和选择性 I 类组蛋白脱乙酰酶抑制剂的开发

  摘要：

  组蛋白脱乙酰酶 (HDAC) 是表观遗传调节剂，另外还控制非组蛋白底物的活性。我们最近证明，抑制在各种癌症中过表达的 HDAC8 会以 T 细胞依赖性方式降低肝细胞癌的致瘤性。在这里，我们提出了基于烷基化酰肼的 I 类 HDAC 抑制剂，其中连接到酰肼部分的正己基侧链在体外表现出 HDAC8 选择性。对最有希望的化合物7d对 HDAC8的抑制模式的分析揭示了一种底物竞争性结合模式。7d显着诱导 HDAC8 底物 H3K27 和 SMC3 的乙酰化，但不诱导 CD4 +中的微管蛋白T 淋巴细胞，并显着上调记忆和效应功能的基因表达。此外，在 C57BL/6 小鼠中腹腔注射7d（10 mg/kg）可增加CD4 + T 细胞和 CD8 + T 细胞比例中的白细胞介素 2表达，且无明显毒性。本研究扩展了具有 T 细胞调节特性的 HDAC8 抑制剂的新型化学型，用于未来的治疗应用。

  DOI：

  10.1021/acs.jmedchem.2c01132

文献信息

• [EN] SUBSTITUTED PIPERAZINYL PYRAZINES AND PYRIDINES AS 5-HT7 RECEPTOR ANTAGONISTS<br/>[FR] PIPÉRAZINYL PYRAZINES ET PYRIDINES SUBSTITUÉES COMME ANTAGONISTES DU RÉCEPTEUR 5-HT7
  申请人：LILLY CO ELI

  公开号：WO2009029439A1

  公开（公告）日：2009-03-05

  The present invention provides selective 5-HT7 receptor antagonist compounds of Formula (I) and their use in the treatment of migraine: where A is C(H)= or N=; m is 0, 1 or 2; R1 is optionally substituted phenyl, optionally substituted pyrazol-4-yl; optionally substituted imidazolyl, optionally substituted pyridyl, or thienyl; R2 is hydrogen or methyl; and R3 and R4 are as defined herein.

  本发明提供了选择性5-HT7受体拮抗剂化合物的公式(I)及其在治疗偏头痛中的应用：其中A为C(H)=或N=；m为0、1或2；R1为可选择取代的苯基、可选择取代的吡唑-4-基；可选择取代的咪唑基、可选择取代的吡啶基或噻吩基；R2为氢或甲基；R3和R4如本文所定义。
• [EN] IMIDAZOPYRIDAZINE COMPOUNDS USEFUL AS MODULATORS OF IL-12, IL-23 AND/OR IFN ALPHA RESPONSES<br/>[FR] COMPOSÉS D'IMIDAZOPYRIDAZINE UTILES EN TANT QUE MODULATEURS DE RÉPONSES D'IL-12, IL-23 ET/OU IFN ALPHA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2020180907A1

  公开（公告）日：2020-09-10

  Compounds having the following formula I: or a stereoisomer or a pharmaceutically-acceptable salt thereof, wherein all substituents are as defined herein, are useful in the modulation of IL-12, IL-23 and/or IFNα by acting on Tyk-2 to cause signal transduction inhibition.

  具有以下化学式I的化合物，或其立体异构体或药用盐，在此定义的所有取代基条件下，可用于通过作用于Tyk-2从而引起信号转导抑制，从而调节IL-12、IL-23和/或IFNα。
• A General Strategy for the Construction of Functionalized Azaindolines via Domino Palladium-Catalyzed Heck Cyclization/Suzuki Coupling
  作者：Tabitha T. Schempp、Blake E. Daniels、Steven T. Staben、Craig E. Stivala

  DOI：10.1021/acs.orglett.7b01606

  日期：2017.7.7

  The preparation of substituted azaindolines utilizing a domino palladium-catalyzed Heck cyclization/Suzuki coupling is described. The approach is amenable for the construction of all four azaindoline isomers. A range of functional groups such as esters, amides, ketones, sulfones, amines, and nitriles are all tolerated under the reaction conditions.

  描述了利用多米诺骨牌钯催化的Heck环化/ Suzuki偶联制备取代的氮杂二氢吲哚。该方法适合于所有四个氮杂二氢吲哚异构体的构建。在反应条件下，可以耐受各种官能团，例如酯，酰胺，酮，砜，胺和腈。
• [EN] INHIBITORS OF MONOACYLGLYCEROL LIPASE AND METHODS OF THEIR USE<br/>[FR] INHIBITEURS DE MONOACYLGLYCÉROL LIPASE ET PROCÉDÉS DE LEUR UTILISATION
  申请人：INFINITY PHARMACEUTICALS INC

  公开号：WO2013049332A1

  公开（公告）日：2013-04-04

  Provided herein are compounds which mediate the activity of monoacyglycerol lipase (MAGL). Also provided are pharmaceutical compositions comprising a compound provided herein, and methods for treating, preventing and/or managing a MAGL mediated condition using a compound or pharmaceutical composition as provided herein.

  本文提供了介导单甘酰基甘油脂肪酶（MAGL）活性的化合物。还提供了包括本文提供的化合物的制药组合物，以及使用本文提供的化合物或制药组合物治疗、预防和/或管理MAGL介导疾病的方法。
• Discovery of 2,6-disubstituted pyrazine derivatives as inhibitors of CK2 and PIM kinases
  作者：Lakshmaiah Gingipalli、Michael H. Block、Larry Bao、Emma Cooke、Les A. Dakin、Christopher R. Denz、Andrew D. Ferguson、Jeffrey W. Johannes、Nicholas A. Larsen、Paul D. Lyne、Timothy W. Pontz、Tao Wang、Xiaoyun Wu、Allan Wu、Hai-Jun Zhang、Xiaolan Zheng、James E. Dowling、Michelle L. Lamb

  DOI：10.1016/j.bmcl.2018.03.018

  日期：2018.5

  The design and synthesis of a novel series of 2,6-disubstituted pyrazine derivatives as CK2 kinase inhibitors is described. Structure-guided optimization of a 5-substituted-3-thiophene carboxylic acid screening hit (3a) led to the development of a lead compound (12b), which shows inhibition in both enzymatic and cellular assays. Subsequent design and hybridization efforts also led to the unexpected

  描述和设计了一系列新型的2,6-二取代吡嗪衍生物作为CK2激酶抑制剂。对5-取代的3-噻吩羧酸筛选结果（3a）进行结构导向的优化导致了前导化合物（12b）的开发，该化合物在酶促和细胞分析中均表现出抑制作用。随后的设计和杂交努力也导致了具有有效PIM激酶活性的类似物的意外鉴定（14f）。