3-hydroxy-4-(benzyloxy)benzonitrile | 194985-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-hydroxy-4-(benzyloxy)benzonitrile
• 英文别名: 3-hydroxy-4-(phenylmethoxy)benzenecarbonitrile；3-hydroxy-4-(phenylmethoxy)benzonitrile；5-cyano-2-benzyloxyphenol；4-benzyloxy-3-hydroxybenzonitrile；2-benzyloxy-5-cyanophenol；4-(benzyloxy)-3-hydroxybenzonitrile；3-Hydroxy-4-benzyloxybenzonitrile；3-hydroxy-4-phenylmethoxybenzonitrile
• CAS: 194985-94-9
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: WXWYOLTXMVROOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  413.8±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-(benzyloxy)benzonitrile 在 盐酸羟胺 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N'-hydroxy-3-methoxy-4-phenylmethoxybenzenecarboximidamide
  参考文献：
  名称：

  Design and Synthesis of 3,5-Disubstituted-1,2,4-Oxadiazoles as Potent Inhibitors of Phosphodiesterase4B2

  摘要：

  A series of 3,5‐disubstituted‐1,2,4‐oxadiazoles has been prepared and evaluated for phosphodiesterase inhibition (PDE4B2). Among the prepared 3,5‐disubstituted‐1,2,4‐oxadiazoles, compound 9a is the most potent inhibitor (PDE4B2 IC50 = 5.28 μm). Structure–activity relationship studies of 3,5‐disubstituted‐1,2,4‐oxadiazoles revealed that substituents 3‐cyclopentyloxy‐4‐methoxyphenyl group at 3‐position and cyclic ring bearing heteroatoms at 5‐position are important for activity. Molecular modeling study of the 3,5‐disubstituted‐1,2,4‐oxadiazoles with PDE4B has shown similar interactions of 3‐cyclopentyloxy‐4‐methoxyphenyl group; however, heteroatom ring is slightly deviating when compared to Piclamilast. 3‐(3‐Cyclopentyloxy‐4‐methoxyphenyl)‐5‐(piperidin‐4‐yl)‐1,2,4‐oxadiazole (9a) exhibited good analgesic and antiinflammatory activities in formalin‐induced pain in mice and carrageenan‐induced paw edema model in rat.

  DOI：

  10.1111/j.1747-0285.2011.01304.x
• 作为产物：
  描述：

  3-羟基-4-苄氧基苯甲醛 在 甲酸 、 盐酸羟胺 、 sodium formate 作用下， 反应 3.0h， 生成 3-hydroxy-4-(benzyloxy)benzonitrile
  参考文献：
  名称：

  Design and Synthesis of 3,5-Disubstituted-1,2,4-Oxadiazoles as Potent Inhibitors of Phosphodiesterase4B2

  摘要：

  A series of 3,5‐disubstituted‐1,2,4‐oxadiazoles has been prepared and evaluated for phosphodiesterase inhibition (PDE4B2). Among the prepared 3,5‐disubstituted‐1,2,4‐oxadiazoles, compound 9a is the most potent inhibitor (PDE4B2 IC50 = 5.28 μm). Structure–activity relationship studies of 3,5‐disubstituted‐1,2,4‐oxadiazoles revealed that substituents 3‐cyclopentyloxy‐4‐methoxyphenyl group at 3‐position and cyclic ring bearing heteroatoms at 5‐position are important for activity. Molecular modeling study of the 3,5‐disubstituted‐1,2,4‐oxadiazoles with PDE4B has shown similar interactions of 3‐cyclopentyloxy‐4‐methoxyphenyl group; however, heteroatom ring is slightly deviating when compared to Piclamilast. 3‐(3‐Cyclopentyloxy‐4‐methoxyphenyl)‐5‐(piperidin‐4‐yl)‐1,2,4‐oxadiazole (9a) exhibited good analgesic and antiinflammatory activities in formalin‐induced pain in mice and carrageenan‐induced paw edema model in rat.

  DOI：

  10.1111/j.1747-0285.2011.01304.x

文献信息

• Benzamidine derivatives and their use as anti-coagulants
  申请人：Berlex Laboratories, Inc.

  公开号：US06350746B1

  公开（公告）日：2002-02-26

  This invention is directed to benzamidine derivatives which are useful as anti-coagulants. This invention is also directed to pharmaceutical compositions containing the compounds of the invention, and methods of using the compounds to treat disease-states characterized by thrombotic activity.

  这项发明涉及对苯甲酰胺衍生物的研究，这些衍生物可用作抗凝剂。该发明还涉及含有该发明中化合物的药物组合物，以及使用这些化合物治疗由血栓活动特征的疾病状态的方法。
• Aryl and heterocyclyl substituted pyrimidine derivatives as anti-coagulants
  申请人：Berlex Laboratories, Inc.

  公开号：US06372751B1

  公开（公告）日：2002-04-16

  This invention is directed to aryl and heterocyclyl substituted pyrimidine derivatives selected from the following formulae: wherein Z1, Z2, R1, R2, R3, R4, R5 and R6 are defined herein. These compounds are useful as anti-coagulants.

  这项发明涉及从以下公式中选择的芳基和杂环基取代的嘧啶衍生物： 其中Z1、Z2、R1、R2、R3、R4、R5和R6在此处定义。这些化合物可用作抗凝剂。
• Purinenucleoside derivative modified in 8-position and medical use thereof
  申请人：Tatani Kazuya

  公开号：US20070179115A1

  公开（公告）日：2007-08-02

  The present invention provides an 8-modified purinenucleoside derivative which is useful for diseases associated with an abnormality of plasma uric acid level. An 8-modified purinenucleoside derivative represented by the following formula (I), a prodrug thereof or a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof, is useful for the prevention or treatment of gout, hyperuricemia, urinary lithiasis, hyperuricemic nephropathy or the like. In the formula, n is 1 or 2; R A is a hydrogen atom or a hydroxyl group; R 1 is a hydrogen atom, a hydroxyl group, a thiol group, an amino group or a chlorine atom; ring J represents an optionally substituted 2-naphthyl group, or a group represented by the following general formula (II) wherein Y represents a single bond or a connecting group; ring Z represents an optionally substituted aryl group or heteroaryl group or the like; and R 2 to R 4 , P 1 and Q represents a halogen atom, a cyano group or the like.

  本发明提供了一种用于与血浆尿酸水平异常相关疾病的8-修饰嘌呤核苷衍生物。以下式（I）所代表的一种8-修饰嘌呤核苷衍生物、其前药或药用盐、或其水合物或溶剂化合物，对于痛风、高尿酸血症、尿路结石、高尿酸性肾病等的预防或治疗具有用处。在该式中，n为1或2；RA是氢原子或羟基；R1是氢原子、羟基、硫醇基、氨基或氯原子；环J代表可选地取代的2-萘基，或由以下一般式（II）所代表的基团，其中Y代表单键或连接基团；环Z代表可选地取代的芳基或杂环芳基等；而R2至R4、P1和Q代表卤素原子、氰基或类似物。
• Bicyclic compositions and methods for modulating a kinase cascade
  申请人：Hangauer David G.

  公开号：US20080004241A1

  公开（公告）日：2008-01-03

  The invention relates to compounds and methods for modulating one or more components of a kinase cascade.

  该发明涉及化合物和方法，用于调节激酶级联中的一个或多个组分。
• Protein kinase and phosphatase inhibitors and methods for designing them
  申请人：——

  公开号：US20030166615A1

  公开（公告）日：2003-09-04

  The present invention provides a method for identifying inhibitors of protein kinases and/or protein phosphatases. Methods are also provided for inhibiting protein kinase and/or protein phosphatase activity. Specific non-peptide protein tyrosine kinase and/or protein phosphatase inhibitors are provided. The protein kinase or protein phosphatase inhibitors of the present invention may be used to treat a number of conditions in patients, including cancer, psoriasis, arthrosclerosis, immune system activity, Type II diabetes, and obesity.

  本发明提供了一种识别蛋白激酶和/或蛋白磷酸酶抑制剂的方法。还提供了用于抑制蛋白激酶和/或蛋白磷酸酶活性的方法。具体的非肽蛋白酪氨酸激酶和/或蛋白磷酸酶抑制剂也被提供。本发明的蛋白激酶或蛋白磷酸酶抑制剂可用于治疗患者的多种疾病，包括癌症、银屑病、动脉粥样硬化、免疫系统活性、2型糖尿病和肥胖症。