2-羟基-5-苯基吡啶 | 76053-45-7

• 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: 2-羟基-5-苯基吡啶
• 英文名称: 5-phenylpyridin-2(1H)-one
• 英文别名: 5-phenyl-2(1H)-pyridone；5-Phenyl-2(1H)-pyridinone；5-Phenylpyridin-2-ol；5-phenyl-1H-pyridin-2-one
• CAS: 76053-45-7
• 化学式: C₁₁H₉NO
• mdl: MFCD11044359
• 分子量: 171.199
• InChiKey: RWFAQYWIBBVEBY-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C
• 沸点：
  394.7±35.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 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: 2-Hydroxy-5-phenylpyridine
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-Hydroxy-5-phenylpyridine
CAS number: 76053-45-7

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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.
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.
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: C11H9NO
Molecular weight: 171.2

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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-羟基-5-苯基吡啶 在 三溴氧磷 作用下， 以 苯甲醚 为溶剂， 反应 3.0h， 以33%的产率得到2-溴-5-苯基吡啶
  参考文献：
  名称：

  Total Syntheses of the Alkaloids Ipalbidinium and Clathryimine B

  摘要：

  The indolizidinium alkaloid ipalbidinium and the quinolizidinium alkaloid clathryimine B were prepared starting from brominated 2-aminopyridines using two Pd-catalyzed cross-coupling reactions and a Sandmeyer-type diazotation/iodination protocol as the key steps.

  DOI：

  10.1007/s00706-002-0540-5
• 作为产物：
  描述：

  5-溴-2-甲氧基吡啶 在 O₄P^(3-)*3K⁽¹⁺⁾*5H₂O 、 吡啶盐酸盐 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.33h， 生成 2-羟基-5-苯基吡啶
  参考文献：
  名称：

  有丝分裂特异性3,4-二氢吡啶-2(1H)-硫酮的合成及其抗癌活性

  摘要：

  大多数抗癌药物将有丝分裂作为癌细胞快速分裂的最关键和最脆弱的时期。然而，经典化疗的局限性促使人们寻找新的更有效和选择性的化合物。为此目的，对先前表征的吡啶类似物（ S1 ）进行结构修饰，旨在获得具有令人满意和特异性抗癌活性的抗有丝分裂抑制剂。对一组癌细胞系的化合物进行结构-活性关系分析，允许选择在 3,4-二氢吡啶-2(1 H )-硫酮 ( S22 ) 的 C5 处具有噻吩环的化合物，具有良好的抗增殖活性 (IC 50等于 1.71 ± 0.58 µM) 和对黑色素瘤 A375 细胞的选择性 (SI = 21.09)。此外，抗增殖研究中所有三种最活跃的化合物，即S1 、 S19和S22对A375细胞表现出比参考药物更好的选择性，表明它们可能具有较低的毒性和更广泛的治疗指数。进一步研究表明，选定的化合物以剂量依赖性方式通过秋水仙碱结合位点抑制微管蛋白聚合，导致异常有丝分裂纺锤体形成、细胞周期

  DOI：

  10.3390/ijms22052462

文献信息

• Inhibitors of Bruton's Tyrosine Kinase
  申请人：Berthel Steven

  公开号：US20100222325A1

  公开（公告）日：2010-09-02

  This application discloses 5-phenyl-1H-pyridin-2-one, 6-phenyl-2H-pyridazin-3-one, and 5-Phenyl-1H-pyrazin-2-one derivatives according to generic Formulae I-III: wherein, variables Q, R, X, X′, Y 1 , Y 2 , Y 2′ , Y 3 , Y 4 , Y 5 , m, and n are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation such as rheumatoid arthritis. Also disclosed are compositions containing compounds of Formulae I-III and at least one carrier, diluent or excipient.

  该应用程序根据通用公式I-III披露了5-苯基-1H-吡啶-2-酮，6-苯基-2H-吡啶-3-酮和5-苯基-1H-吡嗪-2-酮衍生物： 其中，变量Q、R、X、X'、Y1、Y2、Y2'、Y3、Y4、Y5、m和n的定义如本文所述，这些化合物抑制Btk。本文披露的化合物对调节Btk的活性并治疗与过度Btk活性相关的疾病有用。这些化合物进一步有助于治疗与异常B细胞增殖相关的炎症和自身免疫疾病，如类风湿性关节炎。还披露了含有公式I-III化合物和至少一种载体、稀释剂或赋形剂的组合物。
• HETEROCYCLIC COMPOUND AND USE THEREOF
  申请人：Taniguchi Takahiko

  公开号：US20130137675A1

  公开（公告）日：2013-05-30

  The present invention aims to provide a compound having a PDE inhibitory action and useful as a medicament for the prophylaxis or treatment of schizophrenia and the like. A compound represented by the formula (1 x ): wherein each symbol is as described in the DESCRIPTION, or the formula (1): W 1 —W 2 (1) wherein each symbol is as described in the DESCRIPTION, or a salt thereof.

  本发明旨在提供一种具有PDE抑制作用并且用作预防或治疗精神分裂症等疾病的药物的化合物。 由式（1）表示的化合物： 其中每个符号如描述中所述，或式（1）： W1-W2（1） 其中每个符号如描述中所述， 或其盐。
• Aminopyridazines as Acetylcholinesterase Inhibitors
  作者：Jean-Marie Contreras、Yveline M. Rival、Said Chayer、Jean-Jacques Bourguignon、Camille G. Wermuth

  DOI：10.1021/jm981101z

  日期：1999.2.1

  Following the discovery of the weak, competitive and reversible acetylcholinesterase (AChE)-inhibiting activity of minaprine (3c) (IC50 = 85 microM on homogenized rat striatum AChE), a series of 3-amino-6-phenylpyridazines was synthesized and tested for inhibition of AChE. A classical structure-activity relationship exploration suggested that, in comparison to minaprine, the critical elements for high

  发现米那匹林（3c）的弱，竞争性和可逆性乙酰胆碱酯酶（AChE）抑制活性（对均质大鼠纹状体AChE的IC50 = 85 microM）后，合成了一系列3-氨基-6-苯基哒嗪并测试了其抑制作用AChE。一项经典的构效关系研究表明，与米萘普林相比，高乙酰胆碱酯酶抑制的关键因素如下：（i）中央哒嗪环的存在；（ii）亲脂性阳离子头的必要性；（iii）改变哒嗪环与阳离子头之间的碳原子数为2至4-5。在研究的所有衍生物中，3- [2-（1-苄基哌啶-4-基）乙基氨基] -6-苯基哒嗪（3y）在纯化的AChE（电鳗）上的IC50为0.12 microM，
• COMPOUNDS AND METHODS FOR TREATING INFLAMMATORY AND FIBROTIC DISORDERS
  申请人：Kossen Karl

  公开号：US20090318455A1

  公开（公告）日：2009-12-24

  Disclosed are compounds and methods for treating inflammatory and fibrotic disorders, including methods of modulating a stress activated protein kinase (SAPK) system with an active compound, wherein the active compound exhibits low potency for inhibition of the p38 MAPK; and wherein the contacting is conducted at a SAPK-modulating concentration that is at a low percentage inhibitory concentration for inhibition of the p38 MAPK by the compound. Also disclosed are derivatives and analogs of pirfenidone, useful for modulating a stress activated protein kinase (SAPK) system.

  公开了用于治疗炎症和纤维化疾病的化合物和方法，包括用活性化合物调节应激活化蛋白激酶（SAPK）系统的方法，其中活性化合物对p38 MAPK的抑制效力较低；并且其中接触是在SAPK调节浓度下进行的，该浓度对化合物抑制p38 MAPK的抑制浓度百分比较低。还公开了吡非尼酮的衍生物和类似物，它们可用于调节应激活化蛋白激酶（SAPK）系统。
• [EN] INHIBITORS OF BRUTON'S TYROSINE KINASE<br/>[FR] INHIBITEURS DE LA TYROSINE KINASE DE BRUTON
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010122038A1

  公开（公告）日：2010-10-28

  This application discloses 5 -phenyl- 1H-pyridin-2-one, 6-phenyl-2H-pyridazin-3-one, and 5-phenyl-1H-pyrazin-2-one derivatives according to generic Formula A wherein, variables Z* or Q1, Q2, Y3, Y4, Y5 and m are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation such as rheumatoid arthritis. Also disclosed are compositions containing compounds of Formula A and at least one carrier, diluent or excipient.

  该应用程序披露了根据通用式A制备的5-苯基-1H-吡啶-2-酮、6-苯基-2H-吡啉并-3-酮以及5-苯基-1H-吡嗪-2-酮衍生物，其中变量Z*或Q1、Q2、Y3、Y4、Y5和m的定义如本文所述，这些衍生物抑制Btk。本文披露的化合物对调节Btk的活性并治疗与过度Btk活性相关的疾病具有用处。这些化合物还有助于治疗与异常B细胞增殖相关的炎症和自身免疫疾病，如类风湿性关节炎。还披露了含有通用式A化合物和至少一种载体、稀释剂或赋形剂的组合物。