4-(磺酰吡咯啉)苯基硼酸 | 486422-57-5

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 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-(磺酰吡咯啉)苯基硼酸
• 中文别名: 4-(1-吡咯烷基磺酰基)苯硼酸
• 英文名称: (4-(pyrrolidin-1-ylsulfonyl)phenyl)boronic acid
• 英文别名: (4-(pyrrolidine-1-sulphonyl)phenyl)boronic acid；[4-(pyrrolidin-1-ylsulfonyl)phenyl]boronic acid；(4-pyrrolidin-1-ylsulfonylphenyl)boronic acid；(4-boronophenyl)(pyrrolidin-1-yl)sulfone；4-boronophenyl(pyrrolidin-1-ylsulfone)；4-(pyrrolidin-1-ylsulfonyl)phenylboronic acid
• CAS: 486422-57-5
• 化学式: C₁₀H₁₄BNO₄S
• 分子量: 255.102
• InChiKey: LSQCNEYLDWKDHO-UHFFFAOYSA-N

物化性质

• 熔点：
  275-277
• 密度：
  1.41

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2935009090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(Pyrrolidinylsulfonyl)phenylboronic acid
Synonyms: 1-(4-Boronobenzenesulfonyl)pyrrolidine; (4-boronophenyl)(pyrrolidin-1-yl)sulfone; 4-(Pyrrolidin-
1-ylsulfonyl)phenylboronic acid

---

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
P280: Wear protective gloves/protective clothing/eye protection/face protection
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
Store locked up
P405:

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Section 3. Composition/information on ingredients.
Ingredient name: 4-(Pyrrolidinylsulfonyl)phenylboronic acid
CAS number: 486422-57-5

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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.
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.
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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H14BNO4S
Molecular weight: 255.1

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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, sulfur 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-(磺酰吡咯啉)苯基硼酸 、 溴氟甲烷 在 4-二甲氨基吡啶 、 1,10-菲罗啉 、 氯化镍二甲氧基乙烷 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 为溶剂， 反应 24.0h， 以50%的产率得到1-((4-(fluoromethyl)phenyl)sulfonyl)pyrrolidine
  参考文献：
  名称：

  芳基硼酸和氟代甲基溴之间的镍催化交叉偶合，易于接触氟代甲基化的芳烃

  摘要：

  以工业原料氟甲基溴（CH 2 FBr）为偶合伙伴，可实现芳基硼酸的镍催化氟甲基化。反应在温和的反应条件下高效地进行。它具有使用低成本镍催化剂，合成简单和出色的官能团相容性的特点，并提供了容易获得与生物相关的氟甲基化分子的途径。初步的机理研究表明，催化循环涉及单电子转移（SET）途径。

  DOI：

  10.1002/anie.201502882
• 作为产物：
  描述：

  C₁₆H₂₆BNO₄S 在 水 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 生成 4-(磺酰吡咯啉)苯基硼酸
  参考文献：
  名称：

  Discovery of Novel Potent and Highly Selective Glycogen Synthase Kinase-3β (GSK3β) Inhibitors for Alzheimer’s Disease: Design, Synthesis, and Characterization of Pyrazines

  摘要：

  Glycogen synthase kinase-3 beta, also called tau phosphorylating kinase, is a proline-directed serine/threonine kinase which was originally identified due to its role in glycogen metabolism. Active forms of GSK3 beta localize to pretangle pathology including dystrophic neuritis and neurofibrillary tangles in Alzheimer's disease (AD) brain. By using a high throughput screening (HTS) approach to search for new chemical series and cocrystallization of key analogues to guide the optimization and synthesis of our pyrazine series, we have developed highly potent and selective inhibitors showing cellular efficacy and blood-brain barrier penetrance. The inhibitors are suitable for in vivo efficacy testing and may serve as a new treatment strategy for Alzheimer's disease.

  DOI：

  10.1021/jm201724m

文献信息

• [EN] COMPOUNDS AND METHODS FOR CD73 MODULATION AND INDICATIONS THEREFOR<br/>[FR] COMPOSÉS ET PROCÉDÉS DE MODULATION DE CD73 ET LEURS INDICATIONS
  申请人：PLEXXIKON INC

  公开号：WO2021216898A1

  公开（公告）日：2021-10-28

  Disclosed are compounds of Formula (I): or a pharmaceutically acceptable salt, a solvate, a tautomer, a stereoisomer or a deuterated analog thereof, wherein R1, R2, R3, A, E, L, and G are as described in any of the embodiments described in this disclosure; compositions thereof; and uses thereof.

  披露了公式(I)的化合物：或其药用盐、溶剂化物、互变异构体、立体异构体或氘代类似物，其中R1、R2、R3、A、E、L和G如本公开的任何实施方案所述；其组合物；及其用途。
• SUBSTITUTED NAPHTHYLACETIC ACIDS
  申请人：Hoffmann-La Roche Inc.

  公开号：US20130225588A1

  公开（公告）日：2013-08-29

  The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 and X are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds of formula I are antagonists or partial agonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.

  这项发明涉及式(I)的化合物： 及其药学上可接受的盐，其中R 1 ，R 2 ，R 3 和X在详细说明和权利要求中有定义。此外，本发明涉及制造和使用式I的化合物的方法，以及含有这种化合物的药物组合物。式I的化合物是CRTH2受体的拮抗剂或部分激动剂，可能在治疗与该受体相关的疾病和紊乱方面有用，如哮喘。
• [EN] ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014135495A1

  公开（公告）日：2014-09-12

  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.

  本发明公开了化合物的结构式I：其中结构式I中的变量如本文所述。还公开了含有这些化合物的药物组合物，以及使用结构式I中的化合物预防或治疗HCV感染的方法。
• [EN] NOBEL COMPOUNDS HAVING SELECTIVE INHIBITING EFFECT AT GSK3<br/>[FR] NOUVEAUX COMPOSES PRESENTANT UN EFFET INHIBITEUR SELECTIF DE LA GSK3
  申请人：ASTRAZENECA AB

  公开号：WO2004055006A1

  公开（公告）日：2004-07-01

  The present invention relates to new compounds, a process for their preparation and new intermediates used therein, pharmaceutical formulations containing said therapeutically active compounds and to the use of said active compounds in therapy, such as provide compounds having a selective inhibiting effect at GSK3.

  本发明涉及新化合物，其制备方法和其中使用的新中间体，包含上述治疗活性化合物的药物配方，以及该活性化合合物在治疗中的应用，例如提供具有对GSK3具有选择性抑制作用的化合物。
• [EN] PYRAZOLOPYRIMIDINE COMPOUNDS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS DE PYRAZOLOPYRIMIDINE POUR LE TRAITEMENT DU CANCER
  申请人：UNIV NORTH CAROLINA

  公开号：WO2011146313A1

  公开（公告）日：2011-11-24

  Compound of Formula (I): are described, along with pharmaceutically acceptable salts thereof, compositions containing the same, and methods of use thereof in the treatment of cancer.

  化合物的化学式（I）及其药学上可接受的盐被描述，包括含有这些化合物的组合物，以及在癌症治疗中使用它们的方法。