(3-(2-吗啉代乙氧基)苯基)硼酸 | 787591-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (3-(2-吗啉代乙氧基)苯基)硼酸
• 英文名称: 3-(2-morpholin-4-yl-ethoxy)-phenylboronic acid
• 英文别名: 3-(2-morpholinoethoxy)phenylboronic acid；[3-(2-morpholin-4-ylethoxy)phenyl]boronic acid
• CAS: 787591-35-9
• 化学式: C₁₂H₁₈BNO₄
• 分子量: 251.09
• InChiKey: KUXSLEXAYSGYIE-UHFFFAOYSA-N

物化性质

• 沸点：
  458.7±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(2-Morpholinoethoxy)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-(2-Morpholinoethoxy)phenylboronic acid
CAS number: 787591-35-9

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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, under −20◦C.
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: C12H18BNO4
Molecular weight: 251.1

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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.

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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-(2-吗啉代乙氧基)苯基)硼酸 、 2-氯-5-羟基吡啶 在 copper diacetate 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以65%的产率得到4-{2-[3-(6-chloropyridin-3-yloxy)phenoxy]ethyl}morpholine
  参考文献：
  名称：

  PYRIDINE DERIVATIVES FOR THE TREATMENT OF AMYLOID-RELATED DISEASES

  摘要：

  该化合物的结构式（I）或其药用可接受的盐或前药：其中X和Y分别独立为NR5或O；W和Z分别独立为键或（CH2）mCH(R7)(CH2)n；m=0-1，n=0-2；R为氢或卤素；R1和R2分别选自氢卤素，CF3，CN，OR8，NR9R10，NR9COR11，NR9SO2R11或C1-6烷基，可选择地被羟基，C1-6烷氧基或NR9R10取代；R3为氢，卤素，CF3，CN，OR8，SR8或SO2R11；R4为氢，卤素，CF3，OR9，NR9R10，NR9COR11，NR9SO2R11或C1-6烷基，可选择地被羟基，C1-6烷氧基或NR9R10取代；R5为氢或C1-6烷基，可选择地被羟基，C1-6烷氧基或NR9R10取代；R6为氢，氟，C1-6烷基或C1-6烷氧基；R7为氢，C1-6烷基，苯基或C1-3烷基苯基，其中所述苯基可选择地被一个或多个取代基取代，所述取代基选自卤素，C1-6烷基，CF3，OCF3或OR9；R8为氢或C1-6烷基，可选择地被氟，C1-6烷氧基或NR9R10取代；R9为氢，C1-6烷基或C1-3烷基苯基，其中所述苯基可选择地被一个或多个取代基取代，所述取代基选自卤素，C1-6烷基，CF3，OR8，NR9R10或OCF3；R10为氢，C1-6烷基，C1-6烯基，苯基或C1-3烷基苯基，其中所述苯基可选择地被一个或多个取代基取代，所述取代基选自卤素，C1-6烷基，CF3，OR8或OCF3；或当连接到氮原子时，R9和R10组合可形成一个可选择地含有来自NR9，S和O的进一步杂原子的5-或6-成员环；R11为C1-6烷基或一个苯基，可选择地被一个或多个取代基取代，所述取代基选自卤素，C1-6烷基，CF3，OCF3或OR8。这些化合物在治疗与淀粉样蛋白相关的疾病中很有用。

  公开号：

  US20100298325A1
• 作为产物：
  描述：

  [2-(3-bromophenoxy)ethyl]-morpholine 在 正丁基锂 、 硼酸三异丙酯 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以74%的产率得到(3-(2-吗啉代乙氧基)苯基)硼酸
  参考文献：
  名称：

  PYRIDINE DERIVATIVES FOR THE TREATMENT OF AMYLOID-RELATED DISEASES

  摘要：

  该化合物的结构式（I）或其药用可接受的盐或前药：其中X和Y分别独立为NR5或O；W和Z分别独立为键或（CH2）mCH(R7)(CH2)n；m=0-1，n=0-2；R为氢或卤素；R1和R2分别选自氢卤素，CF3，CN，OR8，NR9R10，NR9COR11，NR9SO2R11或C1-6烷基，可选择地被羟基，C1-6烷氧基或NR9R10取代；R3为氢，卤素，CF3，CN，OR8，SR8或SO2R11；R4为氢，卤素，CF3，OR9，NR9R10，NR9COR11，NR9SO2R11或C1-6烷基，可选择地被羟基，C1-6烷氧基或NR9R10取代；R5为氢或C1-6烷基，可选择地被羟基，C1-6烷氧基或NR9R10取代；R6为氢，氟，C1-6烷基或C1-6烷氧基；R7为氢，C1-6烷基，苯基或C1-3烷基苯基，其中所述苯基可选择地被一个或多个取代基取代，所述取代基选自卤素，C1-6烷基，CF3，OCF3或OR9；R8为氢或C1-6烷基，可选择地被氟，C1-6烷氧基或NR9R10取代；R9为氢，C1-6烷基或C1-3烷基苯基，其中所述苯基可选择地被一个或多个取代基取代，所述取代基选自卤素，C1-6烷基，CF3，OR8，NR9R10或OCF3；R10为氢，C1-6烷基，C1-6烯基，苯基或C1-3烷基苯基，其中所述苯基可选择地被一个或多个取代基取代，所述取代基选自卤素，C1-6烷基，CF3，OR8或OCF3；或当连接到氮原子时，R9和R10组合可形成一个可选择地含有来自NR9，S和O的进一步杂原子的5-或6-成员环；R11为C1-6烷基或一个苯基，可选择地被一个或多个取代基取代，所述取代基选自卤素，C1-6烷基，CF3，OCF3或OR8。这些化合物在治疗与淀粉样蛋白相关的疾病中很有用。

  公开号：

  US20100298325A1

文献信息

• Design and Synthesis of Novel Aminoindazole-pyrrolo[2,3-b]pyridine Inhibitors of IKKα That Selectively Perturb Cellular Non-Canonical NF-κB Signalling
  作者：Christopher Riley、Usama Ammar、Aisha Alsfouk、Nahoum G. Anthony、Jessica Baiget、Giacomo Berretta、David Breen、Judith Huggan、Christopher Lawson、Kathryn McIntosh、Robin Plevin、Colin J. Suckling、Louise C. Young、Andrew Paul、Simon P. Mackay

  DOI：10.3390/molecules29153515

  日期：——

  The inhibitory-kappaB kinases (IKKs) IKKα and IKKβ play central roles in regulating the non-canonical and canonical NF-κB signalling pathways. Whilst the proteins that transduce the signals of each pathway have been extensively characterised, the clear dissection of the functional roles of IKKα-mediated non-canonical NF-κB signalling versus IKKβ-driven canonical signalling remains to be fully elucidated. Progress has relied upon complementary molecular and pharmacological tools; however, the lack of highly potent and selective IKKα inhibitors has limited advances. Herein, we report the development of an aminoindazole-pyrrolo[2,3-b]pyridine scaffold into a novel series of IKKα inhibitors. We demonstrate high potency and selectivity against IKKα over IKKβ in vitro and explain the structure–activity relationships using structure-based molecular modelling. We show selective target engagement with IKKα in the non-canonical NF-κB pathway for both U2OS osteosarcoma and PC-3M prostate cancer cells by employing isoform-related pharmacodynamic markers from both pathways. Two compounds (SU1261 [IKKα Ki = 10 nM; IKKβ Ki = 680 nM] and SU1349 [IKKα Ki = 16 nM; IKKβ Ki = 3352 nM]) represent the first selective and potent pharmacological tools that can be used to interrogate the different signalling functions of IKKα and IKKβ in cells. Our understanding of the regulatory role of IKKα in various inflammatory-based conditions will be advanced using these pharmacological agents.