6-甲基吡啶-2-硼酸 | 372963-50-3

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-甲基吡啶-2-硼酸
• 中文别名: 6-甲基-2-吡啶硼酸；2-吡啶-6-甲基硼酸
• 英文名称: (6-methylpyridin-2-yl)boronic acid
• 英文别名: 6-methylpyridin-2-ylboronic acid；6-methylpyridine-2-boronic acid；6-methyl-2-pyridylboronic acid
• CAS: 372963-50-3
• 化学式: C₆H₈BNO₂
• mdl: MFCD03093331
• 分子量: 136.946
• InChiKey: XHSGIZRXEBIOFC-UHFFFAOYSA-N

物化性质

• 沸点：
  311.2±44.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Methylpyridine-2-boronic acid
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: 6-Methylpyridine-2-boronic acid
CAS number: 372963-50-3

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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, under −20◦C.
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: C6H8BNO2
Molecular weight: 136.9

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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-甲基吡啶-2-硼酸 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 生成 3-Cyclopentyl-1-methyl-2-(6-methyl-2-pyridyl)indole-6-carboxylic acid
  参考文献：
  名称：

  Discovery of the First Thumb Pocket 1 NS5B Polymerase Inhibitor (BILB 1941) with Demonstrated Antiviral Activity in Patients Chronically Infected with Genotype 1 Hepatitis C Virus (HCV)

  摘要：

  Combinations of direct acting antivirals (DAAs) that have the potential to suppress emergence of resistant virus and that can be used in interferon-sparing regimens represent a preferred option for the treatment of chronic HCV infection. We have discovered allosteric (thumb pocket 1) non-nucleoside inhibitors of HCV NS5B polymerase that inhibit replication in replicon systems. Herein, we report the late-stage optimization of indole-based inhibitors, which began with the identification of a metabolic liability common to many previously reported inhibitors in this series. By use of parallel synthesis techniques, a sparse matrix of inhibitors was generated that provided a collection of inhibitors satisfying potency criteria and displaying improved in vitro ADME profiles. "Cassette" screening for oral absorption in rat provided a short list of potential development candidates. Further evaluation led to the discovery of the first thumb pocket 1 NS5B inhibitor (BILB 1941) that demonstrated antiviral activity in patients chronically infected with genotype 1 HCV.

  DOI：

  10.1021/jm3006788
• 作为产物：
  描述：

  2-溴-6-甲基吡啶 在 异丙基氯化镁 、 三（三甲代甲硅烷基）硼酸盐 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 以72%的产率得到6-甲基吡啶-2-硼酸
  参考文献：
  名称：

  Improved Synthesis of Azaheteroarylboronic Acids Usingtris-Trimethylsilylborate Under Mild Conditions

  摘要：

  A new family of azaheteroarylboronic acids was synthesized with good yields (70% to 75%). The proposed strategy utilizes an improved transmetalation reaction from Grignard azine reagents and tris-trimethylsilylborate, little. used until now.

  DOI：

  10.1081/scc-120016325

文献信息

• [EN] PYRIDO[4,3-B]PYRAZINE-2-CARBOXAMIDES AS NEUROGENIC AGENTS FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS<br/>[FR] PYRIDO[4,3-B]PYRAZINE-2-CARBOXAMIDES UTILISÉES EN TANT QU'AGENTS NEUROGÈNES DANS LE TRAITEMENT DES TROUBLES NEURODÉGÉNÉRATIFS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015071178A1

  公开（公告）日：2015-05-21

  The present invention relates to compounds of general formula (I), wherein R1 is hydrogen; R2 is hydrogen, lower alkyl, benzyl, lower alkyl substituted by hydroxy or is cycloalkyl optionally substituted by cyano; or R1 and R2 form together with the N-atom to which they are attached a heterocycloalkyl group, optionally containing an additional N, O or S ring atom, and which is optionally substituted by hydroxy; R3 is halogen, phenyl optionally substituted by one or more halogen, cyano, lower alkyl substituted by halogen, lower alkoxy substituted by halogen or by lower alkyl substituted by hydroxy, or is heteroaryl, optionally substituted by lower alkyl or halogen, or is 3,6-dihydro-pyran-4-yl, or is piperidin-1-yl optionally substituted by one or more halogen; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to it corresponding enantiomer and/or optical isomer thereof. The compounds of formula I may be used in the treatment of schizophrenia, obsessive-compulsive personality disorder, depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, cognitive impairment, chemotherapy-induced cognitive dysfunction, Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of neuro-active drugs, selected from alcohol, opiates, methamphetamine, phencyclidine and cocaine.

  本发明涉及一般式(I)的化合物，其中R1为氢；R2为氢、较低的烷基、苄基、被羟基取代的较低烷基或是环烷基，可选择地被氰基取代；或者R1和R2与它们连接的N原子一起形成一个杂环烷基基团，可选择地含有额外的N、O或S环原子，并且可选择地被羟基取代；R3为卤素、苯基，可选择地被一个或多个卤素、氰基、被卤素取代的较低烷基、被卤素取代的较低烷氧基或被羟基取代的较低烷基取代，或者是杂芳基，可选择地被较低烷基或卤素取代，或者是3,6-二氢-吡喃-4-基，或者是哌啶-1-基，可选择地被一个或多个卤素取代；或者是药学上可接受的酸加合物，或者是外消旋混合物，或者是其对应的对映体和/或光学异构体。式(I)的化合物可用于治疗精神分裂症、强迫性人格障碍、抑郁症、躁郁症、焦虑症、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、恐慌障碍、帕金森病、痴呆症、阿尔茨海默病、认知障碍、化疗引起的认知功能障碍、唐氏综合征、自闭症谱系障碍、听力丧失、耳鸣、脊髓小脑共济失调、肌萎缩侧索硬化、多发性硬化症、亨廷顿病、中风、放射治疗、慢性压力、神经活性药物滥用，从酒精、阿片类药物、甲基苯丙胺、芬太尼和可卡因中选择。
• [EN] COMPOSITIONS AND METHODS FOR INHIBITING KINASES<br/>[FR] COMPOSITIONS ET MÉTHODES POUR INHIBER LES KINASES
  申请人：INHIBIKASE THERAPEUTICS INC

  公开号：WO2016172528A1

  公开（公告）日：2016-10-27

  The present invention provides compounds for the prevention or treatment of cancer or a bacterial or viral infection. Additionally, the present invention provides compositions and methods for using these compounds and compositions in the prevention or treatment of cancer or a bacterial or viral infection in a subject.

  本发明提供了用于预防或治疗癌症或细菌或病毒感染的化合物。此外，本发明还提供了在主体中使用这些化合物和组合物进行预防或治疗癌症或细菌或病毒感染的组合物和方法。
• Optimization of spirocyclic proline tryptophan hydroxylase-1 inhibitors
  作者：Daniel R. Goldberg、Stéphane De Lombaert、Robert Aiello、Patricia Bourassa、Nicole Barucci、Qing Zhang、Vishwas Paralkar、Adam J. Stein、Melissa Holt、Jim Valentine、William Zavadoski

  DOI：10.1016/j.bmcl.2016.12.053

  日期：2017.2

  As a follow-up to the discovery of our spirocyclic proline-based TPH1 inhibitor lead, we describe the optimization of this scaffold. Through a combination of X-ray co-crystal structure guided design and an in vivo screen, new substitutions in the lipophilic region of the inhibitors were identified. This effort led to new TPH1 inhibitors with in vivo efficacy when dosed as their corresponding ethyl

  作为我们基于螺环脯氨酸的TPH1抑制剂前导物的发现的后续研究，我们描述了该支架的优化。通过结合X射线共晶体结构指导设计和体内筛选，在抑制剂的亲脂性区域发现了新的取代基。当将它们作为相应的乙酯前药给药时，这种努力导致了具有体内功效的新型TPH1抑制剂。特别是强效TPH1抑制剂15a（KAR5417）的前药15b（KAR5585）在小鼠中显示出肠道5-羟色胺（5-HT）水平的强烈降低。而且，口服15b在大鼠和狗中产生了活性母体15a的高而持续的全身暴露。选择了KAR5585在与功能异常的外周5-HT系统相关的疾病模型中进行进一步的药理评估。
• 3-Substituted biquinolinium inhibitors of AraC family transcriptional activator VirF from S. flexneri obtained through in situ chemical ionization of 3,4-disubstituted dihydroquinolines
  作者：Prashi Jain、Jiaqin Li、Patrick Porubsky、Benjamin Neuenswander、Susan M. Egan、Jeffrey Aubé、Steven Rogers

  DOI：10.1039/c4ra08384a

  日期：——

  During a structure–activity relationship optimization campaign to develop an inhibitor of AraC family transcriptional activators, we discovered an unexpected transformation of a previously reported inhibitor that occurs under the assay conditions. Once placed in the assay media, the 3,4-disubstituted dihydroquinoline core of the active analogue rapidly undergoes a decomposition reaction to a quaternary 3-substituted biquinolinium. Further examination established an SAR for this chemotype while also demonstrating its resilience to irreversible binding of biologically relevant nucleophiles.

  在一次结构-活性关系优化活动中，旨在开发AraC家族转录激活因子的抑制剂，我们发现了一个意外的转化，发生在之前报告的抑制剂在检测条件下。一旦置于检测介质中，活性类似物的3,4-双取代二氢喹啉核心迅速发生分解反应，生成四取代的3-取代双喹啉离子。进一步的研究建立了该化学类型的SAR，同时也展示了其对生物相关亲核体不可逆结合的抗性。
• 一种含金刚烷取代基的吡啶类化合物及其在制备抗肿瘤药物中的用途
  申请人：陈海鹏

  公开号：CN108774167A

  公开（公告）日：2018-11-09

  本发明公开了一种含金刚烷取代基的吡啶类化合物式（Ⅰ）及其在制备抗肿瘤药物中的用途，，其中：R1、R2、R3、R4各自独立的选自H、F或CH3。由药理实验结果可知，本发明化合物具有MNK1激酶抑制作用，其中JMNK‑D002～JMNK‑D004对MNK1激酶抑制活性的IC50小于10nM，并且本发明化合物对人胰腺癌细胞系MiaPaCa2具有较好的体外抑制活性，其中，JMNK‑D001～JMNK‑D004对MiaPaCa2抑制活性的IC50小于10μM。说明本发明化合物可以用于抗癌药物进行研究。