异喹啉-6-硼酸 | 899438-92-7

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 异喹啉-6-硼酸
• 中文别名: 6-异喹啉硼酸
• 英文名称: isoquinolin-6-ylboronic acid
• 英文别名: isoquinoline-6-boronic acid
• CAS: 899438-92-7
• 化学式: C₉H₈BNO₂
• mdl: MFCD10697418
• 分子量: 172.979
• InChiKey: OBUOMTRFSCUDKS-UHFFFAOYSA-N

物化性质

• 沸点：
  419.1±37.0 °C(Predicted)
• 密度：
  1.28

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Isoquinolin-6-ylboronic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: Isoquinolin-6-ylboronic acid
CAS number: 899438-92-7

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels, refrigerated.

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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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H8BNO2
Molecular weight: 173.0

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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：

  异喹啉-6-硼酸 在 palladium diacetate 、 sodium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 1-[4-(2-fluoro-4-isoquinolin-6-ylbenzoyl)piperidin-1-yl]propan-1-one
  参考文献：
  名称：

  [EN] SUBSTITUTED 4-BENZYL AND 4-BENZOYL PIPERIDINE DERIVATIVES
  [FR] DÉRIVÉS DE 4-BENZYL ET 4-BENZOYL-PIPÉRIDINE SUBSTITUÉS

  摘要：

  本文描述了根据公式I的1,4-取代哌啶化合物，这些化合物已经表现出作为脂肪酸合酶抑制剂的活性。本文还描述了含有所述1,4-取代哌啶化合物的药物组合物。本文还描述了通过给予本文描述的一个或多个化合物或药物配方治疗由脂肪酸合酶介导的疾病的方法。本文还描述了合成所述1,4-取代哌啶化合物以及在这些合成中有用的合成中间体的方法。

  公开号：

  WO2016205590A1
• 作为产物：
  描述：

  6-溴异喹啉 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 异喹啉-6-硼酸
  参考文献：
  名称：

  [EN] FUSED RING-CONTAINING COMPOUND, APPLICATION THEREOF, AND COMPOSITION CONTAINING SAME
  [FR] COMPOSÉ CONTENANT UN CYCLE FUSIONNÉ, SON APPLICATION, ET COMPOSITION LE CONTENANT
  [ZH] 一种含稠环的化合物、其应用及含其的组合物

  摘要：

  一种含稠环的化合物、其应用及含其的组合物，具体为一种如式(II)所示的含稠环的化合物、其药学上可接受的盐、其溶剂合物或其药学上可接受的盐的溶剂合物，该类化合物具有较佳的STAT5抑制活性。

  公开号：

  WO2022083731A1
• 作为试剂：
  描述：

  硼酸三异丙酯 、 6-溴异喹啉 、 正丁基锂 、 盐酸 在 solid 、 盐酸 、 异喹啉-6-硼酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 异喹啉-6-硼酸盐酸盐
  参考文献：
  名称：

  FLUOROISOQUINOLINE SUBSTITUTED THIAZOLE COMPOUNDS AND METHODS OF USE

  摘要：

  本发明涉及一种式I的噻唑化合物及其组合物，其在治疗由蛋白激酶B（PKB）介导的疾病方面具有用途，其中变量具有本文所提供的定义。本发明还涉及在治疗与异常细胞生长、癌症、炎症和代谢紊乱有关的疾病状态中使用此类噻唑化合物和其组合物的治疗用途。

  公开号：

  US20110263647A1

文献信息

• [EN] GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE GLYCOLATE OXYDASE POUR LE TRAITEMENT D'UNE MALADIE
  申请人：BIOMARIN PHARM INC

  公开号：WO2020257487A1

  公开（公告）日：2020-12-24

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物，以及使用这种化合物治疗或预防与甘氧酸代谢缺陷相关的疾病或紊乱的方法，例如与甘氧酸氧化酶（GO）或草酸代谢变化相关的疾病或紊乱。这些疾病或紊乱包括与产生过多草酸相关的甘氧酸代谢紊乱，例如原发性高草酸尿症。
• The synthesis of 3-aryl-3-azetidinyl acetic acid esters by rhodium(I)-catalysed conjugate addition of organoboron reagents
  作者：Philip N. Collier

  DOI：10.1016/j.tetlet.2009.04.078

  日期：2009.7

  A practical route to 3-aryl-3-azetidinyl acetic acid esters is developed. The key step involves the rhodium(I)-catalysed conjugate addition of an organoboron reagent to an α,β-unsaturated alkene. Elaboration of one conjugate addition product to give a novel spiroazetidine ring system is also described.

  开发了一种生产3-芳基-3-氮杂环丁烷基乙酸酯的实用方法。关键步骤涉及将有机硼试剂铑（I）催化共轭加成到α，β-不饱和烯烃上。还描述了一种缀合物加成产物的精制以给出新型的螺氮杂环丁烷环系统。
• Synthesis and Biological Evaluation of Analogs of Didehydroepiandrosterone as Potential New Anticancer Agents
  作者：Eirik J. Solum、Sandra Liekens、Trond Vidar Hansen

  DOI：10.3390/molecules25133052

  日期：——

  The synthesis, cytotoxicity and inhibition of CDK8 by thirteen analogs of cortistatin A are reported. These efforts revealed that the analogs with either a 6- or 7-isoquinoline or 5-indole side chain in the 17-position are the most promising anti-proliferative agents. These compounds showed potent cytotoxic effects in CEM, HeLa and HMEC-1 cells. All three compounds exhibited IC50 values < 10µM. The

  报告了 13 种皮质抑素 A 类似物对 CDK8 的合成、细胞毒性和抑制作用。这些努力表明，在 17 位具有 6-或 7-异喹啉或 5-吲哚侧链的类似物是最有前途的抗增殖剂。这些化合物在 CEM、HeLa 和 HMEC-1 细胞中显示出有效的细胞毒性作用。所有三种化合物的 IC50 值均小于 10µM。最有趣的 10l 类似物对人真皮微血管内皮细胞系 (HMEC-1) 的 IC50 值为 0.59 µM，明显低于参考标准 2-甲氧基雌二醇。在 50 nM 的浓度下，最有效的 10 小时化合物将 CDK8 的活性降低到 35%。
• Synthesis and biological evaluations of new analogs of 2-methoxyestradiol: Inhibitors of tubulin and angiogenesis
  作者：Eirik Johansson Solum、Jing-Jy Cheng、Irene B. Sørvik、Ragnhild E. Paulsen、Anders Vik、Trond Vidar Hansen

  DOI：10.1016/j.ejmech.2014.08.002

  日期：2014.10

  The synthesis, cytotoxicity, inhibition of tubulin polymerization and anti-angiogenic effects of 15 analogs of 2-methoxyestradiol (1) are reported. The biological studies revealed that the position of nitrogen atom in the heterocyclic ring is important for inhibition of both tubulin polymerization and angiogenesis. The most potent inhibitors were compounds 11f and 13e, with a 6-substituted isoquinoline

  报道了15种2-甲氧基雌二醇（1）类似物的合成，细胞毒性，微管蛋白聚合的抑制作用和抗血管生成作用。生物学研究表明，氮原子在杂环中的位置对于抑制微管蛋白聚合和血管生成均很重要。最有效的抑制剂是化合物11f和13e，在类固醇骨架的17位上带有6个取代的异喹啉环。此外，对于在10μM浓度下测试的类似物，观察到较低的雌激素活性。
• New CDK8 inhibitors as potential anti-leukemic agents – Design, synthesis and biological evaluation
  作者：Eirik Solum、Trond Vidar Hansen、Reidun Aesoy、Lars Herfindal

  DOI：10.1016/j.bmc.2020.115461

  日期：2020.5

  oncogenes has proved to be important in a variety of cancer types including hematological malignancies. We have designed and synthesized a series of new synthetic steroids. The compounds were evaluated as CDK8 inhibitors in vitro. The three most potent compounds exhibit Kd-values towards CDK8 in the low nanomolar range (3.5-18 nM). Furthermore, the compounds displayed selectivity for CDK8 in a panel of 465

  细胞周期蛋白依赖性激酶8（CDK8）通过与介体复合物结合或通过转录因子的磷酸化在调节细胞转录中起着至关重要的作用。事实证明，CDK8介导的癌基因激活在包括血液系统恶性肿瘤在内的多种癌症中都很重要。我们设计并合成了一系列新的合成类固醇。将该化合物在体外评价为CDK8抑制剂。三种最有效的化合物在低纳摩尔范围（3.5-18 nM）中对CDK8表现出Kd值。此外，这些化合物在一组465种不同的激酶中显示出对CDK8的选择性。细胞研究表明，与正常细胞系相比，杀伤AML癌细胞的选择性更高。