6-(4-吗啉基)-3-吡啶硼酸 | 904326-93-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 6-(4-吗啉基)-3-吡啶硼酸
• 中文别名: 2-(吗啡啉-1-基)吡啶-5-硼酸;；2-吗啉基-5-吡啶硼酸；6-吗啡啉-吡啶-3-硼酸；6-(4-吗啡啉)-3-吡啶硼酸；(6-吗啉代吡啶-3-基)硼酸；2-(吗啡啉-1-基)吡啶-5-硼酸
• 英文名称: (6-morpholinopyridin-3-yl)boronic acid
• 英文别名: [6-(morpholin-4-yl)pyridin-3-yl]boronic acid；6-morpholinopyridine-3-boronic acid；6-(4-morpholino)-3-pyridineboronic acid；6-Morpholinopyridin-3-ylboronic acid；(6-morpholin-4-ylpyridin-3-yl)boronic acid
• CAS: 904326-93-8
• 化学式: C₉H₁₃BN₂O₃
• mdl: MFCD03086116
• 分子量: 208.025
• InChiKey: FFPQELNXDVTLEW-UHFFFAOYSA-N

物化性质

• 沸点：
  458.6±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Morpholinopyridine-3-boronic acid
Synonyms: 6-Morpholinopyridin-3-ylboronic acid

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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: 6-Morpholinopyridine-3-boronic acid
CAS number: 904326-93-8

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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: C9H13BN2O3
Molecular weight: 208.0

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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：

  6-(4-吗啉基)-3-吡啶硼酸 在 盐酸 、 4-二甲氨基吡啶 、 copper diacetate 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 吡啶 、 异丙醇 为溶剂， 反应 44.0h， 生成 2-cyano-1-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)-3-(pyridin-4-yl)guanidine
  参考文献：
  名称：

  发现有效和有效的含氰基胍的烟酰胺磷酸核糖基转移酶（Nampt）抑制剂

  摘要：

  利用含酰胺化合物（4）与烟酰胺磷酸核糖基转移酶（Nampt）蛋白的共晶体结构和分子建模，设计并发现了一种有效的新型含砜基氰基抑制剂，该抑制剂带有砜部分（5，Nampt Biochemical IC 50  ＝ 2.5nM，A2780细胞增殖IC 50  ＝ 9.7nM。SAR的进一步探索发现了另外几种具有高效能和良好微粒体稳定性的含氰基胍的化合物。其中，化合物15选择用于体内谱分析并在小鼠中证明良好的口服暴露。当在A2780卵巢肿瘤异种移植模型中口服给药时，它还表现出优异的体内抗肿瘤功效。还确定了该化合物与NAMPT蛋白复合的共晶体结构。

  DOI：

  10.1016/j.bmcl.2013.11.006
• 作为产物：
  描述：

  4-(5-溴吡啶-2-基)吗啉 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.0h， 生成 6-(4-吗啉基)-3-吡啶硼酸
  参考文献：
  名称：

  新型的双芳基取代的噻唑和恶唑类化合物是高活性和选择性的过氧化物酶体增殖物激活受体δ激动剂。

  摘要：

  从高通量筛选到高效和选择性的过氧化物酶体增殖物激活受体δ（PPARδ）激动剂的发现，合成和优化了化合物1。详细介绍了该系列中的合成和构效关系。基于通用的PPAR药效团模型示意图，支架1将其分为头基，接头和尾基，并使用体外PPAR反式激活分析对PPAR激活进行了优化。有效和选择性的PPARδ活化需要一个（2-甲基苯氧基）乙酸头基，一个柔性连接基和一个带有两个疏水性芳基取代基的五元杂芳族中心环。这些芳基取代基的微调导致了一系列高效且选择性的化合物（例如化合物38c）在小鼠体内表现出出色的药代动力学特性。在体内急性给药模型中，该阵列的选定成员显示出可诱导丙酮酸脱氢酶激酶4（PDK4）和解偶联蛋白3（UCP3）的表达，这些基因已知参与能量稳态并受其调节。骨骼肌中的PPARδ。

  DOI：

  10.1021/jm9007399

文献信息

• SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS
  申请人：GLAXOSMITHKLINE LLC

  公开号：US20150152108A1

  公开（公告）日：2015-06-04

  The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本发明涉及新型取代桥式脲化合物，相应的相关类似物，药物组合物以及其使用方法。本发明的抑制素调节化合物可用于延长细胞寿命，并治疗和/或预防各种疾病和疾病，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块疾病、炎症、癌症和/或潮红有关的疾病或疾病，以及那些会受益于增加线粒体活性的疾病或疾病。本发明还涉及包含抑制素调节化合物与另一治疗剂组合的组合物。
• [EN] SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS<br/>[FR] ANALOGUES D'URÉE PONTÉS SUBSTITUÉS EN TANT QUE MODULATEURS DE SIRTUINE
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2016079709A1

  公开（公告）日：2016-05-26

  The present invention relates to novel substituted bridged urea analog compounds of Formula (I) or pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions, processes for making and use of such compounds, alone or in combination with other therapeutic agents, as Sirtuin Modulators useful for increasing lifespan of a cell, and for use in treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity.

  本发明涉及一种新型的取代桥式脲类似物化合物，其化学式为（I）或其药学上可接受的盐，相应的药物组合物，制备这种化合物的方法以及单独使用或与其他治疗剂联合使用的这些化合物作为Sirtuin调节剂，可用于增加细胞寿命，并用于治疗和/或预防各种疾病和紊乱，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块紊乱、炎症、癌症和/或潮红有关的疾病或紊乱，以及那些会受益于增加线粒体活性的疾病或紊乱。
• Design, synthesis and pharmacological evaluation of a novel mTOR-targeted anti-EV71 agent
  作者：Tianlong Hao、Yuexiang Li、Shiyong Fan、Wei Li、Shixu Wang、Song Li、Ruiyuan Cao、Wu Zhong

  DOI：10.1016/j.ejmech.2019.04.048

  日期：2019.8

  Due to the limitations of existing anti-EV71 targets, we have been eager to discover a new anti-EV71 agent based on mTOR (the mammalian target of rapamycin), which is an important target for finding antiviral agents based on host cells. Torin2 is a second-generation ATP competitive mTOR kinase inhibitor (IC50 = 0.25 nM). Our research team tested the anti-EV71 activity of Torin2 in vitro for the first

  由于现有抗EV71靶标的局限性，我们一直渴望发现一种基于mTOR（雷帕霉素的哺乳动物靶标）的新型抗EV71剂，这是寻找基于宿主细胞的抗病毒剂的重要靶标。Torin2是第二代ATP竞争性mTOR激酶抑制剂（IC 50  = 0.25 nM）。我们的研究团队首次在体外测试了Torin2的抗EV71活性。结果表明，Torin2具有显着的抗EV71活性（IC 50  = 0.01μM）。在这项研究中，合成了三十种新颖的Torin2衍生物，并评估了其抗EV71活性。其中11a，11b，11d，11e和11m显示了与Torin2类似的活动。图11e显示了最有效的活性，最接近Torin2的IC 50值为0.027μM，并且显示了有效的mTOR激酶抑制活性。分子建模研究表明，11e通过氢键与Val2240和Lys2187相互作用，并与受体具有良好的匹配性。此外，一项机理研究表明，大多数化合物对mTOR途径
• Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C–N Bond Activation
  作者：Jennie Liao、Weiye Guan、Brian P. Boscoe、Joseph W. Tucker、John W. Tomlin、Michelle R. Garnsey、Mary P. Watson

  DOI：10.1021/acs.orglett.8b01062

  日期：2018.5.18

  nickel-catalyzed cross-coupling of benzylic pyridinium salts with arylboronic acids was developed. Coupled with chemoselective pyridinium formation, this method allows benzyl primary amines to be efficiently converted to di(hetero)arylmethanes. Excellent heteroaryl and functional group tolerance is observed, and a one-pot procedure enables benzylic amines to be converted to diarylmethanes directly.

  开发了镍催化的苄基吡啶鎓盐与芳基硼酸的交叉偶联。结合化学选择性吡啶鎓的形成，该方法可使苄基伯胺有效地转化为二（杂）芳基甲烷。观察到优异的杂芳基和官能团耐受性，一锅法可使苄基胺直接转化为二芳基甲烷。
• Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C–N Bond Activation
  作者：Prantik Maity、Danielle M. Shacklady-McAtee、Glenn P. A. Yap、Eric R. Sirianni、Mary P. Watson

  DOI：10.1021/ja3089422

  日期：2013.1.9

  We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis

  我们开发了一种镍催化的苄基三氟甲磺酸铵与芳基硼酸的交叉偶联，以提供二芳基甲烷和二芳基乙烷。该反应在温和的反应条件下进行，具有出色的官能团耐受性。此外，它以优异的手性转移将支化的苄基铵盐转化为二芳基乙烷，为从容易获得的手性苄基胺合成高度对映体富集的二芳基乙烷提供了一种新策略。