3-（环丙基磺酰基）苯硼酸 | 1020204-12-9

• 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: 3-（环丙基磺酰基）苯硼酸
• 中文别名: 3-(环丙基磺酰基)苯基硼酸
• 英文名称: 3-(cyclopropylsulfonyl)phenylboronic acid
• 英文别名: (3-(Cyclopropylsulfonyl)phenyl)boronic acid；(3-cyclopropylsulfonylphenyl)boronic acid
• CAS: 1020204-12-9
• 化学式: C₉H₁₁BO₄S
• 分子量: 226.061
• InChiKey: GDGRCJSXOCMCCT-UHFFFAOYSA-N

物化性质

• 沸点：
  512.5±56.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(Cyclopropylsulfonyl)phenylboronic acid
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: 3-(Cyclopropylsulfonyl)phenylboronic acid
CAS number: 1020204-12-9

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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, refrigerated.
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: C9H11BO4S
Molecular weight: 226.1

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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, 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：

  3-（环丙基磺酰基）苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-(3-(cyclopropylsulfonyl)phenyl)-3-(4-(methylsulfonyl)phenyl)pyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  A Novel Pyrazolopyridine with in Vivo Activity in Plasmodium berghei- and Plasmodium falciparum-Infected Mouse Models from Structure–Activity Relationship Studies around the Core of Recently Identified Antimalarial Imidazopyridazines

  摘要：

  Toward improving pharmacokinetics, in vivo efficacy, and selectivity over hERG, structure activity relationship studies around the central core of antimalarial imidazo-pyridazines were conducted. This study led to the identification of potent pyrazolopyridines, which showed good in vivo efficacy and pharmacokinetics profiles. The lead compounds also proved to be very potent in the parasite liver and gametocyte stages, which makes them of high interest.

  DOI：

  10.1021/acs.jmedchem.5b01605

文献信息

• Synthesis, Structure–Activity Relationship, and Mechanistic Studies of Aminoquinazolinones Displaying Antimycobacterial Activity
  作者：Jessica N. Akester、Paul Njaria、Aloysius Nchinda、Claire Le Manach、Alissa Myrick、Vinayak Singh、Nina Lawrence、Mathew Njoroge、Dale Taylor、Atica Moosa、Anthony J. Smith、Elizabeth J. Brooks、Anne J. Lenaerts、Gregory T. Robertson、Thomas R. Ioerger、Rudolf Mueller、Kelly Chibale

  DOI：10.1021/acsinfecdis.0c00252

  日期：2020.7.10

  2-aminoquinazolinone hit compound, sulfone 1 which was optimized for solubility by replacing the sulfone moiety with a sulfoxide 2. The synthesis and structure–activity relationship (SAR) studies identified several compounds with potent antimycobacterial activity, which were metabolically stable and noncytotoxic. Compound 2 displayed favorable in vitro properties and was therefore selected for in vivo

  表型全细胞筛选针对补充有吐温80和铁（GASTE-Fe）的甘油-丙氨酸-盐中的结核分枝杆菌（Mtb）导致鉴定出2-氨基喹唑啉酮命中化合物砜1，该化合物可通过替换来优化溶解度带有亚砜的砜部分2。合成和结构-活性关系（SAR）研究确定了几种具有有效抗分枝杆菌活性的化合物，它们在代谢上稳定且无细胞毒性。化合物2表现出良好的体外特性，因此被选择用于体内药代动力学（PK）研究，发现它被广泛代谢为砜1。两种衍生物均显示出有希望的PK参数。但是，当评估2在急性TB感染小鼠模型中的体内功效时，发现它没有活性。为了了解体外和体内差异，随后使用在不同培养基中培养的不同Mtb菌株在体外对化合物2进行了重新测试。这表明仅在含甘油的介质中观察到了活性，并导致了以下假设：甘油不被Mtb用作主要碳源。如先前所观察到的，在小鼠肺中的这种作用。自发抗性突变体的产生和全基因组测序研究提供了对这一假说的支持，该研究揭示了映射到
• [EN] KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2009129401A8

  公开（公告）日：2009-12-17
• Medicinal Chemistry Optimization of Antiplasmodial Imidazopyridazine Hits from High Throughput Screening of a SoftFocus Kinase Library: Part 2
  作者：Claire Le Manach、Tanya Paquet、Diego Gonzàlez Cabrera、Yassir Younis、Dale Taylor、Lubbe Wiesner、Nina Lawrence、Sylva Schwager、David Waterson、Michael J. Witty、Sergio Wittlin、Leslie J. Street、Kelly Chibale

  DOI：10.1021/jm500887k

  日期：2014.11.13

  On the basis of our recent results on a novel series of imidazopyridazine-based antimalarials, we focused on identifying compounds with improved aqueous solubility and hERG profile while maintaining metabolic stability and in vitro potency. Toward this objective, 41 compounds were synthesized and evaluated for antiplasmodial activity against NF54 (sensitive) and K1 (multidrug resistant) strains of the malaria parasite Plasmodium falciparum and evaluated for both aqueous solubility and metabolic stability. Selected compounds were tested for in vitro hERG activity and in vivo efficacy in the P. berghei mouse model. Several compounds were identified with significantly improved aqueous solubility, good metabolic stability, and a clean hERG profile relative to a previous frontrunner lead compound. A sulfoxide-based imidazopyridazine analog 45, arising from a prodrug-like strategy, was completely curative in the Plasmodium berghei mouse model at 4 x 50 mg/kg po.
• A Novel Pyrazolopyridine with in Vivo Activity in <i>Plasmodium berghei</i>- and <i>Plasmodium falciparum</i><i>-</i>Infected Mouse Models from Structure–Activity Relationship Studies around the Core of Recently Identified Antimalarial Imidazopyridazines
  作者：Claire Le Manach、Tanya Paquet、Christel Brunschwig、Mathew Njoroge、Ze Han、Diego Gonzàlez Cabrera、Sridevi Bashyam、Rajkumar Dhinakaran、Dale Taylor、Janette Reader、Mariette Botha、Alisje Churchyard、Sonja Lauterbach、Theresa L. Coetzer、Lyn-Marie Birkholtz、Stephan Meister、Elizabeth A. Winzeler、David Waterson、Michael J. Witty、Sergio Wittlin、María-Belén Jiménez-Díaz、María Santos Martínez、Santiago Ferrer、Iñigo Angulo-Barturen、Leslie J. Street、Kelly Chibale

  DOI：10.1021/acs.jmedchem.5b01605

  日期：2015.11.12

  Toward improving pharmacokinetics, in vivo efficacy, and selectivity over hERG, structure activity relationship studies around the central core of antimalarial imidazo-pyridazines were conducted. This study led to the identification of potent pyrazolopyridines, which showed good in vivo efficacy and pharmacokinetics profiles. The lead compounds also proved to be very potent in the parasite liver and gametocyte stages, which makes them of high interest.