4-(2-(哌啶-1-基)乙氧基)苯基硼酸频哪醇酯 | 934586-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(2-(哌啶-1-基)乙氧基)苯基硼酸频哪醇酯
• 中文别名: 4-(2-(哌啶-1-基)乙氧基)苯硼酸频那醇酯
• 英文名称: 1-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)piperidine
• 英文别名: 1-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl]piperidine
• CAS: 934586-49-9
• 化学式: C₁₉H₃₀BNO₃
• 分子量: 331.263
• InChiKey: JKCDXXAFGMZLQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  448.9±30.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-(2-(Piperidin-1-yl)ethoxy)phenylboronic acid, pinacol ester
Synonyms: 1-(2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)piperidine

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-(2-(Piperidin-1-yl)ethoxy)phenylboronic acid, pinacol ester
CAS number: 934586-49-9

---

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.

---

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.

---

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.

---

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.
Storage:

---

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.

---

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: C19H30BNO3
Molecular weight: 331.3

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(2-(哌啶-1-基)乙氧基)苯基硼酸频哪醇酯 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Discovery of 1-(4-(4-Amino-3-(4-(2-morpholinoethoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea (CHMFL-FLT3-213) as a Highly Potent Type II FLT3 Kinase Inhibitor Capable of Overcoming a Variety of FLT3 Kinase Mutants in FLT3-ITD Positive AML

  摘要：

  FLT3-ITD mutant has been observed in about 30% of AML patients and extensively studied as a drug discovery target. On the basis of our previous study that ibrutinib (9) exhibited selective and moderate inhibitory activity against FLT3-ITD positive AML cells, through a structure-guided drug design approach, we have discovered a new type II FLT3 kinase inhibitor, compound 14 (CHMFL-FLT3-213), which exhibited highly potent inhibitory effects against FLT3TTD mutant and associated oncogenic mutations (including FLT3-D835Y/H/V, FLT3-ITD-D835Y/I/N/A/G/Del, and FLT3-ITD-F691L). In the cellular context 14 strongly affected FLT3-TTD mediated signaling pathways and induced apoptosis by arresting cell cycle into G0/G1 phase. In the in vivo studies 14 demonstrated an acceptable bioavaOability (F = 19%) and significantly suppressed the tumor growth in MV4-11 cell inoculated xenograft model (15 mg kg(-1) day(-1), TGI = 97%) without exhibiting obvious toxicity. Compound 14 might be a potential drug candidate for FLT3-TTD positive AML.

  DOI：

  10.1021/acs.jmedchem.7b00840
• 作为产物：
  描述：

  N-羟乙基哌啶 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-(2-(哌啶-1-基)乙氧基)苯基硼酸频哪醇酯
  参考文献：
  名称：

  Discovery of 1-(4-(4-Amino-3-(4-(2-morpholinoethoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea (CHMFL-FLT3-213) as a Highly Potent Type II FLT3 Kinase Inhibitor Capable of Overcoming a Variety of FLT3 Kinase Mutants in FLT3-ITD Positive AML

  摘要：

  FLT3-ITD mutant has been observed in about 30% of AML patients and extensively studied as a drug discovery target. On the basis of our previous study that ibrutinib (9) exhibited selective and moderate inhibitory activity against FLT3-ITD positive AML cells, through a structure-guided drug design approach, we have discovered a new type II FLT3 kinase inhibitor, compound 14 (CHMFL-FLT3-213), which exhibited highly potent inhibitory effects against FLT3TTD mutant and associated oncogenic mutations (including FLT3-D835Y/H/V, FLT3-ITD-D835Y/I/N/A/G/Del, and FLT3-ITD-F691L). In the cellular context 14 strongly affected FLT3-TTD mediated signaling pathways and induced apoptosis by arresting cell cycle into G0/G1 phase. In the in vivo studies 14 demonstrated an acceptable bioavaOability (F = 19%) and significantly suppressed the tumor growth in MV4-11 cell inoculated xenograft model (15 mg kg(-1) day(-1), TGI = 97%) without exhibiting obvious toxicity. Compound 14 might be a potential drug candidate for FLT3-TTD positive AML.

  DOI：

  10.1021/acs.jmedchem.7b00840

文献信息

• SUBSTITUTED FUROPYRIDINES FOR THERAPEUTIC USE
  申请人：Masarykova Univerzita

  公开号：EP4353727A1

  公开（公告）日：2024-04-17

  The invention relates to furopyridine compounds of formula I: for use in the treatment of FLT3-related, DDR-related and MAP4K-related diseases.

  本发明涉及具有式I结构式的环状吡啶衍生物，用于治疗FLT3相关性疾病、DDR相关性疾病和MAP4K相关性疾病。
• Optimization of microtubule affinity regulating kinase (MARK) inhibitors with improved physical properties
  作者：David L. Sloman、Njamkou Noucti、Michael D. Altman、Dapeng Chen、Andrea C. Mislak、Alexander Szewczak、Mansuo Hayashi、Lee Warren、Tammy Dellovade、Zhenhua Wu、Jacob Marcus、Deborah Walker、Hua-Poo Su、Suzanne C. Edavettal、Sanjeev Munshi、Michael Hutton、Hugh Nuthall、Matthew G. Stanton

  DOI：10.1016/j.bmcl.2016.02.003

  日期：2016.9

  Inhibition of microtubule affinity regulating kinase (MARK) represents a potentially attractive means of arresting neurofibrillary tangle pathology in Alzheimer's disease. This manuscript outlines efforts to optimize a pyrazolopyrimidine series of MARK inhibitors by focusing on improvements in potency, physical properties and attributes amenable to CNS penetration. A unique cylcyclohexyldiamine scaffold was identified that led to remarkable improvements in potency, opening up opportunities to reduce MW, Pgp efflux and improve pharmacokinetic properties while also conferring improved solubility. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis and growth inhibition activity of fluorinated derivatives of tamoxifen
  作者：Bianca Malo-Forest、Grégory Landelle、Jessye-Ann Roy、Jacques Lacroix、René C. Gaudreault、Jean-François Paquin

  DOI：10.1016/j.bmcl.2013.01.057

  日期：2013.3

  The design and synthesis of 11 fluorinated derivatives of tamoxifen are described. Growth inhibition values (GI(50)) on human HT-29, M21, MCF7, and MDA-MB-231 tumor cells are also reported. In general, the GI(50) values are similar or slightly higher than tamoxifen with the most active compound on MCF7 cell line having a GI(50) = 3.6 mu M. Surprisingly, as opposed to tamoxifen, both geometrical isomers behave similarly. We hypothesize that this behavior is due to in vitro isomerization of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.
• CN116178248
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of 1-(4-(4-Amino-3-(4-(2-morpholinoethoxy)phenyl)-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-1-yl)phenyl)-3-(5-(<i>tert</i>-butyl)isoxazol-3-yl)urea (CHMFL-FLT3-213) as a Highly Potent Type II FLT3 Kinase Inhibitor Capable of Overcoming a Variety of FLT3 Kinase Mutants in FLT3-ITD Positive AML
  作者：Aoli Wang、Xixiang Li、Cheng Chen、Hong Wu、Ziping Qi、Chen Hu、Kailin Yu、Jiaxin Wu、Juan Liu、Xiaochuan Liu、Zhenquan Hu、Wei Wang、Wenliang Wang、Wenchao Wang、Li Wang、Beilei Wang、Qingwang Liu、Lili Li、Jian Ge、Tao Ren、Shanchun Zhang、Ruixiang Xia、Jing Liu、Qingsong Liu

  DOI：10.1021/acs.jmedchem.7b00840

  日期：2017.10.26

  FLT3-ITD mutant has been observed in about 30% of AML patients and extensively studied as a drug discovery target. On the basis of our previous study that ibrutinib (9) exhibited selective and moderate inhibitory activity against FLT3-ITD positive AML cells, through a structure-guided drug design approach, we have discovered a new type II FLT3 kinase inhibitor, compound 14 (CHMFL-FLT3-213), which exhibited highly potent inhibitory effects against FLT3TTD mutant and associated oncogenic mutations (including FLT3-D835Y/H/V, FLT3-ITD-D835Y/I/N/A/G/Del, and FLT3-ITD-F691L). In the cellular context 14 strongly affected FLT3-TTD mediated signaling pathways and induced apoptosis by arresting cell cycle into G0/G1 phase. In the in vivo studies 14 demonstrated an acceptable bioavaOability (F = 19%) and significantly suppressed the tumor growth in MV4-11 cell inoculated xenograft model (15 mg kg(-1) day(-1), TGI = 97%) without exhibiting obvious toxicity. Compound 14 might be a potential drug candidate for FLT3-TTD positive AML.