[2-(叔丁氧羰基氨基)嘧啶-5-基]硼酸频哪醇酯 | 1032758-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: [2-(叔丁氧羰基氨基)嘧啶-5-基]硼酸频哪醇酯
• 中文别名: 2-(叔丁氧基羰基氨基)嘧啶-5-硼酸频那醇酯
• 英文名称: tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-ylcarbamate
• 英文别名: tert-Butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate；tert-butyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]carbamate
• CAS: 1032758-88-5
• 化学式: C₁₅H₂₄BN₃O₄
• 分子量: 321.184
• InChiKey: XICHESWFGOSKMN-UHFFFAOYSA-N

物化性质

• 密度：
  1.13

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R43
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(tert-Butoxycarbonylamino)pyrimidine-5-boronic acid, pinacol ester
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: 2-(tert-Butoxycarbonylamino)pyrimidine-5-boronic acid, pinacol ester
CAS number: 1032758-88-5

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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: C15H24BN3O4
Molecular weight: 321.2

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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：

  [2-(叔丁氧羰基氨基)嘧啶-5-基]硼酸频哪醇酯 在 bis-triphenylphosphine-palladium(II) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium on activated charcoal 、 氢气 、 sodium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  Discovery of 2-(2-aminopyrimidin-5-yl)-4-morpholino- N -(pyridin-3-yl)quinazolin-7-amines as novel PI3K/mTOR inhibitors and anticancer agents

  摘要：

  In this study, a series of novel 7 or 8-substituted 4-morpholine-quinazoline derivatives was designed and synthesized. Their PI3K alpha inhibitory activities, antiproliferative activities against seven cancer cell lines, namely, PC-3, DU145, MCF-7, BT474, SK-BR-3, U937 and A431, were evaluated in vitro. Compound 17f proved to be a potential drug candidate with high PI3K alpha inhibition activity (IC50 = 4.2 nM) and good antiproliferative activity. Compound 17f was also tested for its inhibitory activities against other kinases, such as PI3K beta, PI3K gamma, PI3K delta and mTOR, its effects on p-Akt (S473) and cell cycle. These results suggested that compound 17f could significantly inhibit the PI3K/Akt/mTOR pathway as a potent PI3K inhibitor and anticancer agent. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.038
• 作为产物：
  描述：

  2-(二苯基亚甲胺)-5-溴嘧啶 、 二碳酸二叔丁酯 反应 12.0h， 以71%的产率得到[2-(叔丁氧羰基氨基)嘧啶-5-基]硼酸频哪醇酯
  参考文献：
  名称：

  Preparation of Aminoaryl and Aminoheteroaryl Boronic Acids and Derivatives Thereof

  摘要：

  该发明涉及一种制备氨基芳基或氨基杂环基硼酸和酯及其盐的方法，其中可选择地取代的氨基芳基或氨基杂环基化合物通过与羰基化合物缩合而在其氮位点得到保护，随后进行金属化并与适当的硼化合物转化。根据随后的处理和去除保护基，得到相应的硼酸、酸酐或其酯。

  公开号：

  US20080269523A1

文献信息

• 신규 하이드록사메이트 유도체 및 이를 포함하는 암의 예방 또는 치료용 약제학적 조성물
  申请人：HANMI PHARM. CO., LTD. 한미약품 주식회사(120100356638) Corp. No ▼ 134811-0197550BRN ▼124-87-00613

  公开号：KR20160038598A

  公开（公告）日：2016-04-07

  본 발명은 신규한 하이드록사메이트 유도체 또는 이의 약학적으로 허용 가능한 염, 및 이를 활성성분으로 함유하는 암의 예방 또는 치료용 약제학적 조성물에 관한 것이다. 본 발명에서 제공하는 신규 하이드록사메이트 유도체 또는 이의 약학적으로 허용 가능한 염은 세포 내 DNA 팩킹 구조를 제어하는 신호전달에 관여하는 히스톤 디아세틸라제-3(Histone Deacetylase-3)를 선택적으로 억제하여 기존의 pan-HDAc 억제제의 독성적 한계를 해결하면서, 암세포의 성장을 효과적으로 억제할 수 있다.

  本发明涉及一种新的羟基甲酰胺衍生物或其药学上可接受的盐，以及含有其作为活性成分的用于预防或治疗癌症的药学组合物。本发明提供的新羟基甲酰胺衍生物或其药学上可接受的盐通过选择性抑制参与细胞内DNA包装结构调控的信号传导的组蛋白去乙酰化酶-3（Histone Deacetylase-3），可以有效抑制癌细胞的生长，同时解决传统泛HDAc抑制剂的毒性限制。
• [EN] THIAZOLOPYRIMIDINE P13K INHIBITOR COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS INHIBITEURS DE LA PI3K À BASE DE THIAZOLOPYRIMIDINE
  申请人：GENENTECH INC

  公开号：WO2009042607A1

  公开（公告）日：2009-04-02

  Compounds of Formulas (Ia and Ib), and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formula Ia and Ib for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  化合物的公式（Ia和Ib），包括立体异构体、几何异构体、互变异构体、溶剂合物、代谢物和其药用可接受的盐，可用于抑制包括PI3K在内的脂质激酶，并用于治疗由脂质激酶介导的癌症等疾病。公开了使用公式Ia和Ib的化合物进行体外、原位和体内诊断、预防或治疗哺乳动物细胞中的这种疾病或相关病理状况的方法。
• Synthesis and PI 3-Kinase Inhibition Activity of Some Novel 2,4,6-Trisubstituted 1,3,5-Triazines
  作者：Ronald Nelson、Taylor Schronce、Yue Huang、Alanoud Albugami、George Kulik、Mark Welker

  DOI：10.3390/molecules23071628

  日期：——

  A number of new trisubstituted triazine phosphatidylinositol 3-kinase (PI3K) inhibitors were prepared via a three-step procedure utilizing sequential nucleophilic aromatic substitution and cross-coupling reactions. All were screened as PI3K inhibitors relative to the well-characterized PI3K inhibitor, ZSTK474. The most active inhibitors prepared here were 2⁻4 times more potent than ZSTK474. A leucine

  通过三步法使用顺序亲核芳族取代和交叉偶联反应，制备了许多新型三取代三嗪磷脂酰肌醇3-激酶（PI3K）抑制剂。相对于特征明确的PI3K抑制剂ZSTK474，所有化合物均被筛选为PI3K抑制剂。此处制备的活性最高的抑制剂的效力是ZSTK474的2至4倍。亮氨酸连接子与最活跃的抑制剂连接，因为它在被前列腺特异性抗原切割后仍保留在任何含肽的前药上，并且不能阻止蛋白激酶B（Akt）磷酸化的抑制，因此抑制由PI3K修饰的抑制剂。
• PHOSPHOINOSITIDE 3-KINASE INHIBITOR COMPOUNDS AND METHODS OF USE
  申请人：Bayliss Tracy

  公开号：US20080242665A1

  公开（公告）日：2008-10-02

  Compounds of Formulas Ia-d where X is S or O, mor is a morpholine group, and R 3 is a monocyclic heteroaryl group, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for modulating the activity of lipid kinases including PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formula Ia-d for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  化学式Ia-d的化合物，其中X为S或O，mor为吗啡啶基团，R3为单环杂芳基团，包括立体异构体、几何异构体、互变异构体、溶剂化物、代谢物和药学上可接受的盐，可用于调节脂质激酶包括PI3K的活性，并用于治疗由脂质激酶介导的癌症等疾病。本文公开了使用化合物Ia-d的方法，用于哺乳动物细胞中体外、体内诊断、预防或治疗这种疾病或相关病理条件。
• Phosphoinositide 3-kinase inhibitor compounds and methods of use
  申请人：Piramed Limited

  公开号：US07888352B2

  公开（公告）日：2011-02-15

  Compounds of Formulas Ia-d where X is S or O, mor is a morpholine group, and R3 is a monocyclic heteroaryl group, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for modulating the activity of lipid kinases including PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formula Ia-d for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  公式Ia-d的化合物，其中X为S或O，mor为吗啡啶基团，R3为单环杂芳基团，包括立体异构体、几何异构体、互变异构体、溶剂化物、代谢物和药学上可接受的盐，对于调节脂质激酶（包括PI3K）的活性以及治疗由脂质激酶介导的癌症等疾病是有用的。公开了使用公式Ia-d的化合物进行哺乳动物细胞的体外、体内和原位诊断、预防或治疗此类疾病或相关病理情况的方法。