B-[6-(1-吡咯烷)-3-吡啶]硼酸 | 1150114-75-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: B-[6-(1-吡咯烷)-3-吡啶]硼酸
• 英文名称: (6-(pyrrolidin-1-yl)pyridin-3-yl)boronic acid
• 英文别名: (6-pyrrolidin-1-yl-3-pyridyl)boronic acid；6-(Pyrrolidin-1-yl)pyridine-3-boronic acid；(6-pyrrolidin-1-ylpyridin-3-yl)boronic acid
• CAS: 1150114-75-2
• 化学式: C₉H₁₃BN₂O₂
• mdl: MFCD06801704
• 分子量: 192.025
• InChiKey: XRIDMVCUHIKAFT-UHFFFAOYSA-N

物化性质

• 沸点：
  421.3±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  56.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-(Pyrrolidin-1-yl)pyridine-3-boronic acid
Synonyms: 2-(Pyrrolidin-1-yl)pyridine-5-boronic 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-(Pyrrolidin-1-yl)pyridine-3-boronic acid
CAS number: 1150114-75-2

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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: C9H13BN2O2
Molecular weight: 192.0

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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：

  B-[6-(1-吡咯烷)-3-吡啶]硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 四丁基氯化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 21.0h， 生成 2,4-Diphenyl-6-[2-(6-pyrrolidin-1-ylpyridin-3-yl)dibenzofuran-4-yl]-1,3,5-triazine
  参考文献：
  名称：

  含氮化合物、电子元件及电子装置

  摘要：

  本公开提供一种含氮化合物、电子元件及电子装置，涉及有机材料技术领域。该含氮化合物如式I所示，其中，X选自氧或硫；R选自杂环烷基、杂芳基；L选自单键、亚芳基、亚杂芳基；R的取代基选自氘、硝基、羟基、烷基、环烷基、烯基、炔基、芳基、杂芳基、杂环烷基、烷氧基、芳基甲硅烷基或烷基甲硅烷基；L的取代基选自氘、硝基、羟基、烷基、环烷基、烯基、炔基、杂环烷基、烷氧基、烷基甲硅烷基、芳基甲硅烷基、芳氧基、芳硫基。本公开的含氮化合物能够降低电子元件的工作电压、提高器件效率和延长器件寿命。

  公开号：

  CN111018847A
• 作为产物：
  描述：

  硼酸三甲酯 、 5-溴-2-(吡咯烷-1-基)吡啶 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以53%的产率得到B-[6-(1-吡咯烷)-3-吡啶]硼酸
  参考文献：
  名称：

  含氮化合物、电子元件及电子装置

  摘要：

  本公开提供一种含氮化合物、电子元件及电子装置，涉及有机材料技术领域。该含氮化合物如式I所示，其中，X选自氧或硫；R选自杂环烷基、杂芳基；L选自单键、亚芳基、亚杂芳基；R的取代基选自氘、硝基、羟基、烷基、环烷基、烯基、炔基、芳基、杂芳基、杂环烷基、烷氧基、芳基甲硅烷基或烷基甲硅烷基；L的取代基选自氘、硝基、羟基、烷基、环烷基、烯基、炔基、杂环烷基、烷氧基、烷基甲硅烷基、芳基甲硅烷基、芳氧基、芳硫基。本公开的含氮化合物能够降低电子元件的工作电压、提高器件效率和延长器件寿命。

  公开号：

  CN111018847A

文献信息

• 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
• Chan–Evans–Lam <i>N</i>1-(het)arylation and <i>N</i>1-alkеnylation of 4-fluoroalkylpyrimidin-2(1<i>H</i>)-ones
  作者：Viktor M Tkachuk、Oleh O Lukianov、Mykhailo V Vovk、Isabelle Gillaizeau、Volodymyr A Sukach

  DOI：10.3762/bjoc.16.191

  日期：——

  derivatives of the corresponding pyrimidines. An efficient C–N bond-forming process is also observed by using boronic acid pinacol esters as coupling partners in the presence of Cu(II) acetate and boric acid. The 4-fluoroalkyl group on the pyrimidine ring significantly assists in the formation of the target N1-substituted products, in contrast to the 4-methyl and 4-unsubstituted substrates which do not undergo

  的赞埃文斯-Lam反应1-未取代-4- fluoroalkylpyrimidin-2（1 Н） -酮与芳基硼酸报告为简便的合成路线，以迄今不可用Ñ 1-（杂）芳基和Ñ的1-烯衍生物相应的嘧啶。在乙酸铜（II）和硼酸的存在下，通过使用硼酸频哪醇酯作为偶联伙伴，也观察到了有效的C–N键形成过程。与在相似的反应条件下不进行N 1-芳基化的4-甲基和4-未取代的底物相反，嘧啶环上的4-氟烷基大大地帮助了目标N 1-取代的产物的形成。
• Synthesis and in Vitro Screening of Phenylbipyridinylpyrazole Derivatives as Potential Antiproliferative Agents
  作者：Mohammad Al-Sanea、Ahmed Elkamhawy、Ahmed Zakaria、Byung Park、Youngjoo Kwon、So Lee、Sang Lee、In Kim

  DOI：10.3390/molecules20011031

  日期：——

  A series of phenylbipyridinylpyrazoles was synthesized through the reaction of 2-(4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl)acetonitrile (4) with different 6-substituted pyridine-3-ylboronic acids. The final compounds 5a–j were screened at 10 µM against over 60 tumor cell lines at the U.S. National Cancer Institute (NCI). In light of the NCI results, compounds 5c and 5h showed a broad spectrum of activity against NCI cell lines with mean growth of 53% and 58%, respectively. Compound 5e behaved differently as it showed high degree of selectivity and potency by inhibiting 96% of growth of leukemia SR cell line at 10 µM. Standard COMPARE analyses were performed at the GI50 level and the results exhibit high correlation in the form of pairwise correlation coefficient (PCC) of more than 0.6 between three of the current compounds and three standard known anticancer agents. Compound 5e demonstrated high correlation levels with merbarone (NSC S336628) with a PCC value of 0.631. Compound 5h showed a considerably high PCC value of 0.626 with dichloroallyl lawsone, while compound 5i, showed PCC values of 0.601 and 0.604 with both dichloroallyl lawsone and N,N-dibenzyldaunomycin (NSC S268242), respectively. These three standard agents have anticancer activity via two major mechanism of actions, inhibition of topoisomerase II and inhibition of biosynthesis of pyrimidine nucleotides, therefore, compounds 5a–j are promising therapeutic agents for targeting different human malignancies. Prediction of drug-likeness and toxicity of these newly synthesized derivatives were also considered.

  一系列苯基双吡啶基吡唑化合物通过2-(4-(2-氯吡啶-4-基)-3-(3-甲氧基-5-甲基苯基)-1H-吡唑-1-基)乙腈（4）与不同的6-取代吡啶-3-基硼酸的反应合成。最终化合物5a–j在美国国家癌症研究所（NCI）以10 µM的浓度筛选了超过60种肿瘤细胞系。根据NCI的结果，化合物5c和5h对NCI细胞系展现出广泛的活性，平均抑制率分别为53%和58%。化合物5e的表现有所不同，其在10 µM浓度下对白血病SR细胞系的生长抑制率达到96%，表现出高度选择性和效能。标准COMPARE分析在GI50水平上进行，结果显示当前三种化合物与三种已知抗癌药物之间的成对相关系数(PCC)高于0.6。化合物5e与美巴龙（NSC S336628）表现出较高的相关性，PCC值为0.631。化合物5h与二氯烯丙基溶碱素的PCC值为0.626，而化合物5i与二氯烯丙基溶碱素和N,N-二苄基道努霉素（NSC S268242）的PCC值分别为0.601和0.604。这三种标准药物通过两种主要机制发挥抗癌活性，即抑制拓扑异构酶 II 和抑制嘧啶核苷酸的生物合成，因此，化合物5a–j是针对不同人类恶性肿瘤的有希望的治疗剂。此外，还考虑了这些新合成衍生物的药物相似性和毒性预测。
• Novel 1,2-dihydroquinazolin-2-ones: Design, synthesis, and biological evaluation against Trypanosoma brucei
  作者：ThanhTruc Pham、Madeline Walden、Christopher Butler、Rosario Diaz-Gonzalez、Guiomar Pérez-Moreno、Gloria Ceballos-Pérez、Veronica Gomez-Pérez、Raquel García-Hernández、Henry Zecca、Emma Krakoff、Brian Kopec、Ogar Ichire、Caden Mackenzie、Marika Pitot、Luis Miguel Ruiz、Francisco Gamarro、Dolores González-Pacanowska、Miguel Navarro、Amy B. Dounay

  DOI：10.1016/j.bmcl.2017.07.032

  日期：2017.8

  published report of the high-throughput screen of >42,000 kinase inhibitors from GlaxoSmithKline against T. brucei identified 797 potent and selective hits. From this rich data set, we selected NEU-0001101 (1) for hit-to-lead optimization. Through our preliminary compound synthesis and SAR studies, we have confirmed the previously reported activity of 1 in a T. brucei cell proliferation assay and have identified

  2014年，已发表的报告对葛兰素史克公司的布鲁氏杆菌进行了高通量筛选，筛选了> 42,000种激酶抑制剂，鉴定出797种有效和选择性的药物。从这个丰富的数据集中，我们选择了NEU-0001101（1）进行潜在客户优化。通过我们的初步化合物合成和SAR的研究中，我们已经证实了先前报道的活动1在锥虫细胞增殖试验，并已确定替代群体，以取代吡啶环1。相对于1，吡唑24在效能和亲脂性上均得到了改善，同时还显示出良好的体外代谢稳定性。特区于图24为进一步优化用于抗锥虫药物发现的新型支架提供了新的方向。
• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：McCall John M.

  公开号：US20120232056A1

  公开（公告）日：2012-09-13

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，并将其应用作药物治疗疾病。还提供了抑制人类或动物主体中PAS激酶（PASK）活性的方法，以治疗糖尿病等疾病。