4-(2-羧基乙基)苯硼酸 | 166316-48-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 4-(2-羧基乙基)苯硼酸
• 中文别名: 4-(2-羧基乙基)苯基硼酸
• 英文名称: 4-(2-carboxyethyl)benzeneboronic acid
• 英文别名: 3-(4-boronophenyl)propanoic acid；4-(2-carboxyethyl)phenylboronic acid
• CAS: 166316-48-9
• 化学式: C₉H₁₁BO₄
• mdl: MFCD01318119
• 分子量: 193.995
• InChiKey: VPSARXNVXCRDIV-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160°C
• 沸点：
  419.2±47.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  14
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-(2-Carboxyethyl)phenylboronic acid
Product Name:
Synonyms: 3-(4-Boronophenyl)propionic 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-(2-Carboxyethyl)phenylboronic acid
Ingredient name:
CAS number: 166316-48-9

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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: C9H11BO4
Molecular weight: 194.0

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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.

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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-(2-羧基乙基)苯硼酸 在 palladium diacetate 、 sodium hydride 、 sodium carbonate 、 三苯基膦 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  N-Hydroxyindole-based inhibitors of lactate dehydrogenase against cancer cell proliferation

  摘要：

  Current cancer research is being increasingly focused on the study of distinctive characters of tumour metabolism, resulting in a switch from oxidative phosphorylation to glycolysis (Warburg effect). Isoform 5 of human lactate dehydrogenase (hLDH5), which catalyzes the final step in the glycolytic cascade (pyruvate to lactate), constitutes a relatively new and untapped anti-cancer target. In this study, careful design and synthesis of a selected series of aryl-substituted N-hydroxyindole-2-carboxylates (NHIs) has led to several hLDH5-inhibitors, showing "first-in-class" potency and isoform selectivity. Enzyme kinetics studies indicated that these inhibitors exhibit a competitive mode of inhibition. Some representative examples were tested against two human pancreatic carcinoma cell lines, and displayed a good antiproliferative activity, which was even more evident under hypoxic conditions. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.046
• 作为产物：
  描述：

  对溴苯丙酸乙酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydroxide 、 potassium acetate 、 二乙醇胺 作用下， 以 二甲基亚砜 、 异丙醇 为溶剂， 反应 33.0h， 生成 4-(2-羧基乙基)苯硼酸
  参考文献：
  名称：

  与有机硼烷合成。十三。ω-（4-溴苯基）链烷酸的合成及其硼化

  摘要：

  通过氢硼化-热异构化-氧化，从1-溴-4-烯基苯5c - e获得ω-（4-溴苯基）链烷酸2c - e。通过与4,4,5,5,4'，4'，5'，5'-八甲基[2.2'] bi的交叉偶联反应，将它们的酯11c - e转化为相应的硼酸酯12c - e的高收率。离子液体[bmim] [BF 4 ]中的[[1,3,2]二恶硼硼烷基]（10）。使用频哪醇硼烷在离子液体中进行偶联反应可得到脱溴产物，并降低了12c - e的收率。3-（4-溴苯基）丙酸乙酯（通过与[2,2']双[[1,3,2]二氧杂硼烷基]交叉偶联，将7c）转化成3-（4- [1,3,2]二恶硼硼烷基）丙酸乙酯（9c）。

  DOI：

  10.1016/s0022-328x(02)01383-9

文献信息

• Substrate Activity Screening:  A Fragment-Based Method for the Rapid Identification of Nonpeptidic Protease Inhibitors
  作者：Warren J. L. Wood、Andrew W. Patterson、Hiroyuki Tsuruoka、Rishi K. Jain、Jonathan A. Ellman

  DOI：10.1021/ja0547230

  日期：2005.11.1

  A new fragment-based method for the rapid development of novel and distinct classes of nonpeptidic protease inhibitors, Substrate Activity Screening (SAS), is described. This method consists of three steps: (1) a library of N-acyl aminocoumarins with diverse, low molecular weight N-acyl groups is screened to identify protease substrates using a simple fluorescence-based assay, (2) the identified N-acyl

  描述了一种新的基于片段的方法，用于快速开发新型和不同类别的非肽蛋白酶抑制剂，即底物活性筛选 (SAS)。该方法由三个步骤组成：(1) 筛选具有多种低分子量 N-酰基的 N-酰基氨基香豆素库，以使用简单的基于荧光的测定来鉴定蛋白酶底物，(2) 已鉴定的 N-酰基氨基香豆素底物通过快速类似物合成和评估进行优化，并且 (3) 优化的底物通过用已知机制的药效团直接替换氨基香豆素而转化为抑制剂。SAS 方法已成功应用于与自身免疫性疾病有关的半胱氨酸蛋白酶组织蛋白酶 S。在筛选 N-酰基氨基香豆素文库时鉴定出多种不同类别的非肽底物。两种非肽底物类别针对底物进行了优化，每个类别的切割效率提高了 8000 倍以上。然后将选择的非肽底物直接转化为对组织蛋白酶 S 具有纳摩尔亲和力的低分子量新型醛抑制剂。本研究证明了这种基于底物的快速鉴定和优化弱片段方法的独特特征和优点，并提供了框架用于开发针对许多不同蛋白酶的完全非肽抑制剂。
• [EN] MODIFIED C-3 BETULINIC ACID DERIVATIVES AS HIV MATURATION INHIBITORS<br/>[FR] DÉRIVÉS D'ACIDE BÉTULINIQUE MODIFIÉS EN C-3, UTILISÉS COMME INHIBITEURS DE MATURATION DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011153315A1

  公开（公告）日：2011-12-08

  Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, modified C-3 betulinic acid and other structurally related natural products derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors. These compounds are useful for the treatment of HIV and AIDS.

  具有药物和生物活性的化合物、其药物组合物及其使用方法被详述。特别是，提供了经修改的C-3白桦酸和其他具有独特抗病毒活性的结构相关天然产物衍生物，用作HIV成熟抑制剂。这些化合物用于治疗HIV和艾滋病。
• A DNA‐Encoded Chemical Library Incorporating Elements of Natural Macrocycles
  作者：Cedric J. Stress、Basilius Sauter、Lukas A. Schneider、Timothy Sharpe、Dennis Gillingham

  DOI：10.1002/anie.201902513

  日期：2019.7.8

  Here we show a seven‐step chemical synthesis of a DNA‐encoded macrocycle library (DEML) on DNA. Inspired by polyketide and mixed peptide‐polyketide natural products, the library was designed to incorporate rich backbone diversity. Achieving this diversity, however, comes at the cost of the custom synthesis of bifunctional building block libraries. This study outlines the importance of careful retrosynthetic

  在这里，我们展示了在DNA上进行DNA编码的大环文库（DEML）的七步化学合成。受聚酮化合物和肽-聚酮化合物混合天然产物的启发，该文库旨在整合丰富的骨架多样性。但是，要实现这种多样性，就要以双功能构件块库的定制合成为代价。这项研究概述了在DNA编码文库中仔细进行逆向合成设计的重要性，同时揭示了需要新的DNA合成方法的领域。
• INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：INFINITY PHARMACEUTICALS, INC.

  公开号：US20150368278A1

  公开（公告）日：2015-12-24

  The present invention provides compounds, and pharmaceutically acceptable compositions thereof, encompassed by any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof. The present invention also provides methods for treating an FAAH mediated disease, disorder or condition by administering a therapeutically effective amount of a compound or composition comprising a compound of any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof, to a patient in need thereof. Additionally, the present invention provides methods for inhibiting FAAH by administering a therapeutically effective amount of a compound or composition comprising a compound of any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof, to a patient in need thereof.

  本发明提供了由任何公式（I）、（II）、（III）、（IV）、（V）或（VI）中的任何化合物及其药学上可接受的组合物所包含的范围，或其亚属所包含的范围。本发明还提供了通过向需要的患者投与任何公式（I）、（II）、（III）、（IV）、（V）或（VI）中的任何化合物或其组合物的治疗有效量来治疗FAAH介导的疾病、紊乱或症状的方法。此外，本发明提供了通过向需要的患者投与任何公式（I）、（II）、（III）、（IV）、（V）或（VI）中的任何化合物或其组合物的治疗有效量来抑制FAAH的方法。
• [EN] COMPOUNDS, DEVICES, AND USES THEREOF<br/>[FR] COMPOSÉS, DISPOSITIFS ET UTILISATIONS ASSOCIÉES
  申请人：SIGILON THERAPEUTICS INC

  公开号：WO2018067615A1

  公开（公告）日：2018-04-12

  The present invention provides compounds, e.g., compounds of Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are implantable elements (e.g., devices and materials) comprising the same, as well as methods of use thereof, e.g., for treating or preventing a disease, disorder, or condition.

  本发明提供化合物，例如，具有式（I）的化合物和药用可接受的盐、溶剂化合物、水合物、互变异构体、立体异构体、同位素标记衍生物及其组合物。还提供包括相同化合物的可植入元件（例如，设备和材料），以及使用方法，例如，用于治疗或预防疾病、紊乱或状况。