4-(3-环戊基脲)苯硼酸频哪酯 | 874297-80-0

• 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-(3-环戊基脲)苯硼酸频哪酯
• 中文别名: 4-(3-环戊基L脲)苯基硼酸频哪醇酯
• 英文名称: N-cyclopentyl-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea
• 英文别名: 1-Cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea；1-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea
• CAS: 874297-80-0
• 化学式: C₁₈H₂₇BN₂O₃
• 分子量: 330.235
• InChiKey: XIRYAWDMLJRGHR-UHFFFAOYSA-N

物化性质

• 沸点：
  444.1±37.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(3-Cyclopentyllureido)phenylboronic acid, pinacol ester
Synonyms: 1-Cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea

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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: 4-(3-Cyclopentyllureido)phenylboronic acid, pinacol ester
CAS number: 874297-80-0

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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.
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: C18H27BN2O3
Molecular weight: 330.2

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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：

  4-(3-环戊基脲)苯硼酸频哪酯 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.67h， 生成 (S)-1-(4-(1-(1-acryloylpyrrolidin-3-yl)-4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)-3-cyclopentylurea
  参考文献：
  名称：

  一系列新型吡咯并[2,3-d]嘧啶/吡唑并[3,4-d]嘧啶-4-胺衍生物作为FGFRs-主要多靶点受体酪氨酸激酶抑制剂的设计、合成和生物学评价胃癌

  摘要：

  胃癌是全球第二大致命癌症。随着治疗手段的进步，早期胃癌的5年生存率可达95%以上。然而，晚期胃癌的预后和生存时间仍然很严峻。因此，迫切需要更有效的胃癌治疗靶向疗法。FGFR、VEGFR 和其他受体酪氨酸激酶最近被建议作为胃癌治疗的潜在靶标。我们在此报告了吡咯并[2,3 - d ]嘧啶/吡唑并[3,4- d ]嘧啶-4-胺衍生物作为一类新型FGFRs-显性多靶受体酪氨酸激酶抑制剂的发现。SAR 评估确定了最活跃的化合物8f和8k，对多种受体酪氨酸激酶显示出极好的抑制活性。此外，8f和8k在 SNU-16 胃癌细胞系中表现出优异的效力。此外，8f和8k可以抑制 FGFR1 磷酸化和下游信号通路以及诱导细胞凋亡。在体内，8f和8k在 SNU-16 异种移植模型中抑制肿瘤生长，而不会引起明显的毒性。这些发现提高了化合物8f和8k可能作为治疗胃癌的潜在药物的可能性。

  DOI：

  10.1016/j.bioorg.2022.105965
• 作为产物：
  描述：

  环戊基异氰酸酯 、 4-氨基苯硼酸频哪醇酯 以 二氯甲烷 为溶剂， 生成 4-(3-环戊基脲)苯硼酸频哪酯
  参考文献：
  名称：

  一系列新型吡咯并[2,3-d]嘧啶/吡唑并[3,4-d]嘧啶-4-胺衍生物作为FGFRs-主要多靶点受体酪氨酸激酶抑制剂的设计、合成和生物学评价胃癌

  摘要：

  胃癌是全球第二大致命癌症。随着治疗手段的进步，早期胃癌的5年生存率可达95%以上。然而，晚期胃癌的预后和生存时间仍然很严峻。因此，迫切需要更有效的胃癌治疗靶向疗法。FGFR、VEGFR 和其他受体酪氨酸激酶最近被建议作为胃癌治疗的潜在靶标。我们在此报告了吡咯并[2,3 - d ]嘧啶/吡唑并[3,4- d ]嘧啶-4-胺衍生物作为一类新型FGFRs-显性多靶受体酪氨酸激酶抑制剂的发现。SAR 评估确定了最活跃的化合物8f和8k，对多种受体酪氨酸激酶显示出极好的抑制活性。此外，8f和8k在 SNU-16 胃癌细胞系中表现出优异的效力。此外，8f和8k可以抑制 FGFR1 磷酸化和下游信号通路以及诱导细胞凋亡。在体内，8f和8k在 SNU-16 异种移植模型中抑制肿瘤生长，而不会引起明显的毒性。这些发现提高了化合物8f和8k可能作为治疗胃癌的潜在药物的可能性。

  DOI：

  10.1016/j.bioorg.2022.105965

文献信息

• Thienopyridine urea inhibitors of KDR kinase
  作者：H. Robin Heyman、Robin R. Frey、Peter F. Bousquet、George A. Cunha、Maria D. Moskey、Asma A. Ahmed、Niru B. Soni、Patrick A. Marcotte、Lori J. Pease、Keith B. Glaser、Melinda Yates、Jennifer J. Bouska、Daniel H. Albert、Candace L. Black-Schaefer、Peter J. Dandliker、Kent D. Stewart、Paul Rafferty、Steven K. Davidsen、Michael R. Michaelides、Michael L. Curtin

  DOI：10.1016/j.bmcl.2006.12.015

  日期：2007.3

  A series of substituted thienopyridine ureas was prepared and evaluated for enzymatic and cellular inhibition of KDR kinase activity. Several of these analogs, such as 2, are potent inhibitors of KDR (<10 nM) in both enzymatic and cellular assays. Further characterization of inhibitor 2 indicated that this analog possessed excellent in vivo potency (ED50 2.1 mg/kg) as measured in an estradiol-induced mouse uterine edema model.
• Discovery of <i>N</i>-(4-(3-Amino-1<i>H</i>-indazol-4-yl)phenyl)-<i>N</i>‘-(2-fluoro-5-methylphenyl)urea (ABT-869), a 3-Aminoindazole-Based Orally Active Multitargeted Receptor Tyrosine Kinase Inhibitor
  作者：Yujia Dai、Kresna Hartandi、Zhiqin Ji、Asma A. Ahmed、Daniel H. Albert、Joy L. Bauch、Jennifer J. Bouska、Peter F. Bousquet、George A. Cunha、Keith B. Glaser、Christopher M. Harris、Dean Hickman、Jun Guo、Junling Li、Patrick A. Marcotte、Kennan C. Marsh、Maria D. Moskey、Ruth L. Martin、Amanda M. Olson、Donald J. Osterling、Lori J. Pease、Niru B. Soni、Kent D. Stewart、Vincent S. Stoll、Paul Tapang、David R. Reuter、Steven K. Davidsen、Michael R. Michaelides

  DOI：10.1021/jm061280h

  日期：2007.4.1

  In our continued efforts to search for potent and novel receptor tyrosine kinase (RTK) inhibitors as potential anticancer agents, we discovered, through a structure-based design, that 3-aminoindazole could serve as an efficient hinge-binding template for kinase inhibitors. By incorporating an N,N'-diaryl urea moiety at the C4-position of 3-aminodazole, a series of RTK inhibitors were generated, which potently inhibited the tyrosine kinase activity of the vascular endothelial growth factor receptor and the platelet-derived growth factor receptor families. A number of compounds with potent oral activity were identified by utilizing an estradiol-induced mouse uterine edema model and an HT1080 human fibrosarcoma xenograft tumor model. In particular, compound 17p (ABT-869) was found to possess favorable pharmacokinetic profiles across different species and display significant tumor growth inhibition in multiple preclinical animal models.
• Design, synthesis and biological evaluation of a series of novel pyrrolo[2,3-d]pyrimidin/pyrazolo[3,4-d]pyrimidin-4-amine derivatives as FGFRs-dominant multi-target receptor tyrosine kinase inhibitors for the treatment of gastric cancer
  作者：Xiuli Wu、Zhihao Liu、Cailin Gan、Wei Wei、Qianyu Zhang、Hongyao Liu、Hanyun Que、Xingping Su、Lin Yue、Hualong He、Liang Ouyang、Tinghong Ye

  DOI：10.1016/j.bioorg.2022.105965

  日期：2022.10

  have recently been suggested as potential targets for gastric cancer treatment. We herein report the discovery of pyrrolo[2,3-d]pyrimidin/pyrazolo[3,4-d]pyrimidin-4-amine derivatives as a new class of FGFRs-dominant multi-target receptor tyrosine kinase inhibitors. SAR assessment identified the most active compounds 8f and 8k, which showed excellent inhibitory activity against a variety of receptor tyrosine

  胃癌是全球第二大致命癌症。随着治疗手段的进步，早期胃癌的5年生存率可达95%以上。然而，晚期胃癌的预后和生存时间仍然很严峻。因此，迫切需要更有效的胃癌治疗靶向疗法。FGFR、VEGFR 和其他受体酪氨酸激酶最近被建议作为胃癌治疗的潜在靶标。我们在此报告了吡咯并[2,3 - d ]嘧啶/吡唑并[3,4- d ]嘧啶-4-胺衍生物作为一类新型FGFRs-显性多靶受体酪氨酸激酶抑制剂的发现。SAR 评估确定了最活跃的化合物8f和8k，对多种受体酪氨酸激酶显示出极好的抑制活性。此外，8f和8k在 SNU-16 胃癌细胞系中表现出优异的效力。此外，8f和8k可以抑制 FGFR1 磷酸化和下游信号通路以及诱导细胞凋亡。在体内，8f和8k在 SNU-16 异种移植模型中抑制肿瘤生长，而不会引起明显的毒性。这些发现提高了化合物8f和8k可能作为治疗胃癌的潜在药物的可能性。