3-氰基-3-羟基联苯 | 154848-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氰基-3-羟基联苯
• 中文别名: 3-(3-羟基苯基)苯乙腈；3-(3-羟基苯基)苯甲腈；3-(3-羟基苯基)苯腈
• 英文名称: 3'-hydroxybiphenyl-3-carbonitrile
• 英文别名: 3-(3-Hydroxyphenyl)benzonitrile
• CAS: 154848-43-8
• 化学式: C₁₃H₉NO
• 分子量: 195.221
• InChiKey: IYDCWWPOHIRIQG-UHFFFAOYSA-N

物化性质

• 熔点：
  105-109 °C(lit.)
• 沸点：
  401.4±38.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 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：
  44
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn,N
• 安全说明：
  S26
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  UN 3077 9/PG 3
• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Cyano-3’-hydroxybiphenyl
Synonyms: 3’-Hydroxybiphenyl-3-carbonitrile

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H312: Harmful in contact with skin
H318: Causes serious eye damage
H332: Harmful if inhaled
H411: Toxic to aquatic life with long lasting effects
P273: Avoid release to the environment
P280: Wear protective gloves/protective clothing/eye protection/face protection
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: 3-Cyano-3’-hydroxybiphenyl
CAS number: 154848-43-8

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H9NO
Molecular weight: 195.2

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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

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3'-(aminomethyl)-[1,1'-biphenyl]-3-ol	862541-17-1	C13H13NO	199.252
  ——	3'-(piperidin-4-yloxy)biphenyl-3-carbonitrile	1352012-62-4	C18H18N2O	278.354
  ——	Cyclohexyl-carbamic acid 3''''-cyano-biphenyl-3-yl ester	681161-73-9	C20H20N2O2	320.391

反应信息

• 作为反应物：
  描述：

  3-氰基-3-羟基联苯 在 氢气 作用下， 以 甲醇 、 异丙醇 为溶剂， 以94%的产率得到3'-(aminomethyl)-[1,1'-biphenyl]-3-ol
  参考文献：
  名称：

  Identification of orally bioavailable, non-amidine inhibitors of Urokinase Plasminogen Activator (uPA)

  摘要：

  In this Letter we report the synthesis and evaluation of a series of non-amidine inhibitors of Urokinase Plasminogen Activator (uPA). Starting from compound 1, a significant change provided compounds in which the amidine, binding in the S1 pocket, was replaced with a primary amine. Further modifications led to the identification of potent, selective, and orally bioavailable uPA inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.008
• 作为产物：
  描述：

  间溴苯甲腈 、 3-羟基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到3-氰基-3-羟基联苯
  参考文献：
  名称：

  Cyclohexylcarbamic Acid 3‘- or 4‘-Substituted Biphenyl-3-yl Esters as Fatty Acid Amide Hydrolase Inhibitors:  Synthesis, Quantitative Structure−Activity Relationships, and Molecular Modeling Studies

  摘要：

  Fatty acid amide hydrolase (FAAH) is a promising target for modulating endocannabinoid and fatty acid ethanolamide signaling, which may have important therapeutic potential. We recently described a new class of O-arylcarbamate inhibitors of FAAH, including the cyclohexylcarbamic acid biphenyl-3-yl ester URB524 (half-maximal inhibitory concentration, IC50 = 63 nM), which have significant anxiolytic-like properties in rats. In the present study, by introducing a selected group of substituents at the meta and para positions of the distal phenyl ring of URB524, we have characterized structure-activity profiles for this series of compounds and shown that introduction of small polar groups in the meta position greatly improves inhibitory potency. Most potent in the series was the m-carbamoyl derivative URB597 (4i, IC50 = 4.6 nM). Furthermore, quantitative structure-activity relationship (QSAR) analysis of an extended set of meta-substituted derivatives revealed a negative correlation between potency and lipophilicity and suggested that small-sized substituents may undertake polar interactions with the binding pocket of the enzyme. Docking studies and molecular dynamics simulations, using the crystal structure of FAAH, indicated that the O-biphenyl scaffold of the carbamate inhibitors can be accommodated within a lipophilic region of the substrate-binding site, where their folded shape mimics the initial 10-12 carbon atoms of the arachidonyl moiety of anandamide (a natural FAAH substrate) and methyl arachidonyl fluorophosphonate (a nonselective FAAH inhibitor). Moreover, substituents at the meta position of the distal. phenyl ring can form hydrogen bonds with atoms located on the polar section of a narrow channel pointing toward the membrane-associated side of the enzyme. The structure-activity characterization reported here should help optimize the pharmacodynamic and pharmacokinetic properties of this class of compounds.

  DOI：

  10.1021/jm031140x

文献信息

• 8-Azabicyclo[3.2.1]octane derivatives
  申请人：Napier Elizabeth Susan

  公开号：US20070185156A1

  公开（公告）日：2007-08-09

  The present invention relates to a 8-azabicyclo[3.2.1]octane derivative of Formula I, wherein each of the substituents is given the definition as set forth in the specification and claims, or a pharmaceutically acceptable salt thereof or solvate thereof. The present invention also relates to a pharmaceutical composition comprising an 8-azabicyclo[3.2.1]octane derivative in admixture with one or more pharmaceutically acceptable auxiliaries and to the use of the 8-azabicyclo[3.2.1]octane derivative in therapy.

  本发明涉及一种式I的8-氮杂双环[3.2.1]辛烷衍生物，其中每个取代基的定义如规范和声明中所述，或其药学上可接受的盐或溶剂。本发明还涉及一种药物组合物，其包括8-氮杂双环[3.2.1]辛烷衍生物与一种或多种药学上可接受的辅助剂混合，并且涉及在治疗中使用8-氮杂双环[3.2.1]辛烷衍生物。
• 3-Hydroxypyrimidine-2,4-diones as Selective Active Site Inhibitors of HIV Reverse Transcriptase-Associated RNase H: Design, Synthesis, and Biochemical Evaluations
  作者：Jing Tang、Feng Liu、Eva Nagy、Lena Miller、Karen A. Kirby、Daniel J. Wilson、Bulan Wu、Stefan G. Sarafianos、Michael A. Parniak、Zhengqiang Wang

  DOI：10.1021/acs.jmedchem.5b01879

  日期：2016.3.24

  achieve selective RNase H inhibition. Biochemical studies showed the two subtypes with an N-1 methyl group (9 and 10) inhibited RNase H in low micromolar range without siginificantly inhibiting RT polymerase, whereas the N-1 unsubstituted subtype 11 inhibited RNase H in submicromolar range and RT polymerase in low micromolar range. Subtype 11 also exhibited substantially reduced inhibition in the HIV-1

  人类免疫缺陷病毒（HIV）逆转录酶（RT）相关的核糖核酸酶H（RNase H）仍然是未经验证的抗病毒靶标。特异性靶向HIV RNase H的主要挑战来自对RT聚合酶（pol）和整合酶（IN）链转移（ST）抑制作用的普遍缺乏选择性。我们在此报告了三种新颖的3-羟基嘧啶-2,4-二酮（HPD）亚型的合成和生化评估，这些亚型经过精心设计以实现选择性RNase H抑制。生化研究表明，具有N-1甲基的两个亚型（9和10）在低微摩尔范围内抑制RNase H，而未显着抑制RT聚合酶，而N-1未取代的亚型11在亚微摩尔范围内抑制RNase H，在低微摩尔范围内抑制RT聚合酶。亚型11在HIV-1 INST分析中也表现出明显降低的抑制作用，在细胞生存力分析中没有明显的细胞毒性，这表明它可能适合进一步的结构-活性关系（SAR），以鉴定具有抗病毒活性的RNase H抑制剂。
• [EN] SUBSTITUTED PARA-BIPHENYLOXYMETHYL DIHYDRO OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF<br/>[FR] PARA-BIPHÉNYLOXYMÉTHYL-DIHYDRO-OXAZOLOPYRIMIDINONES SUBSTITUÉES, LEUR PRÉPARATION ET LEUR UTILISATION
  申请人：SANOFI AVENTIS

  公开号：WO2011034828A1

  公开（公告）日：2011-03-24

  The present invention relates to a series of substituted para-biphenyloxymethyl dihydro oxazolopyrimidinones of formula (I) as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, cognition deficit disorders, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.

  本发明涉及一系列以本文所定义的式(I)的取代对联苯氧甲基二氢噁唑吡咯嘧啶酮。本发明还涉及制备这些化合物的方法，包括新颖的中间体。本发明的化合物是代谢型谷氨酸受体（mGluR），特别是mGluR2受体的调节剂。因此，本发明的化合物在药物代理方面是有用的，特别是在治疗和/或预防各种中枢神经系统疾病（CNS），包括但不限于急性和慢性神经退行性疾病、精神病、认知缺陷症、癫痫、焦虑、抑郁、偏头痛、疼痛、睡眠障碍和呕吐等方面。
• [EN] HEXAFLUOROISOPROPYL CARBAMATE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION<br/>[FR] DÉRIVÉS DE CARBAMATE D'HEXAFLUOROISOPROPYLE, LEUR PRÉPARATION ET LEUR APPLICATION THÉRAPEUTIQUE
  申请人：SANOFI SA

  公开号：WO2011151808A1

  公开（公告）日：2011-12-08

  The invention relates to hexafluoroisopropyl carbamate derivatives of general formula (I): wherein R, Z, A, m and n as defined in the description, in the form of the base or of an addition salt with an acid. The compounds can be used as inhibitors of the enzyme MGL (monoacyl glycerol lipase).

  该发明涉及一般式（I）的六氟异丙基氨甲酸酯衍生物，其中R、Z、A、m和n如描述中所定义，以盐基形式或与酸的加成盐形式存在。这些化合物可用作酶MGL（单酰基甘油脂酶）的抑制剂。
• Synergism of a Novel 1,2,4-oxadiazole-containing Derivative with Oxacillin against Methicillin-Resistant Staphylococcus aureus
  作者：Elisabetta Buommino、Simona De Marino、Martina Sciarretta、Marialuisa Piccolo、Carmen Festa、Maria Valeria D’Auria

  DOI：10.3390/antibiotics10101258

  日期：——

  Staphylococcusaureus is an important opportunistic pathogen that causes many infections in humans and animals. The inappropriate use of antibiotics has favored the diffusion of methicillin-resistant S. aureus (MRSA), nullifying the efforts undertaken in the discovery of antimicrobial agents. Oxadiazole heterocycles represent privileged scaffolds for the development of new drugs because of their unique bioisosteric properties, easy synthesis, and therapeutic potential. A vast number of oxadiazole-containing derivatives have been discovered as potent antibacterial agents against multidrug-resistant MRSA strains. Here, we investigate the ability of a new library of oxadiazoles to contrast the growth of Gram-positive and Gram-negative strains. The strongest antimicrobial activity was obtained with compounds 3 (4 µM) and 12 (2 µM). Compound 12, selected for further evaluation, was found to be noncytotoxic on the HaCaT cell line up to 25 µM, bactericidal, and was able to improve the activity of oxacillin against the MRSA. The highest synergistic interaction was obtained with the combination values of 0.78 μM for compound 12, and 0.06 μg/mL for oxacillin. The FIC index value of 0.396 confirms the synergistic effect of compound 12 and oxacillin. MRSA treatment with compound 12 reduced the expression of genes included in the mec operon. In conclusion, 12 inhibited the growth of the MRSA and restored the activity of oxacillin, thus resulting in a promising compound in the treatment of MRSA infection.

  金黄色葡萄球菌是一种重要的机会性病原体，会引起人类和动物的许多感染。抗生素的不当使用促进了甲氧西林耐药金黄色葡萄球菌（MRSA）的传播，使寻找抗微生物药物的努力化为泡影。噁二唑杂环代表了用于开发新药物的特权骨架，因为它们具有独特的生物同位素性能、易于合成和治疗潜力。已经发现了大量含有噁二唑的衍生物作为有效的抗多药耐药MRSA菌株的抗菌剂。在这里，我们研究了一个新的噁二唑化合物库对抗革兰氏阳性和阴性菌株生长的能力。化合物3（4 µM）和12（2 µM）显示出最强的抗菌活性。选择化合物12进行进一步评估，发现其对HaCaT细胞系的细胞毒性低至25 µM，对细菌具有杀菌作用，并能够提高对MRSA的氧氧西林活性。化合物12与氧氧西林的组合值为0.78 μM，氧氧西林为0.06 μg/mL，具有最高的协同作用。FIC指数值为0.396，证实了化合物12和氧氧西林的协同作用。使用化合物12治疗MRSA降低了包括在mec操纵子中的基因的表达。总之，化合物12抑制了MRSA的生长并恢复了氧氧西林的活性，因此在治疗MRSA感染中是一种有前途的化合物。