2-hydroxy-8-phenyloctanenitrile | 1101136-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-8-phenyloctanenitrile
• CAS: 1101136-32-6
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: MYAZPNQIUUADKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  7-苯基-1-庚醇	7-phenylheptan-1-ol	3208-25-1	C13H20O	192.301
  ——	7-phenylheptanal	121784-15-4	C13H18O	190.285

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-hydroxy-8-phenyloctanoic acid	1101136-35-9	C14H20O3	236.311
  ——	methyl 2-hydroxy-8-phenyloctanimidate	1369796-48-4	C15H23NO2	249.353
  ——	methyl 2-hydroxy-8-phenyloctanoate	1369796-49-5	C15H22O3	250.338

反应信息

• 作为反应物：
  描述：

  2-hydroxy-8-phenyloctanenitrile 在 盐酸 、 水 作用下， 生成 2-hydroxy-8-phenyloctanamide
  参考文献：
  名称：

  Structure–activity relationships of natural and non-natural amino acid-based amide and 2-oxoamide inhibitors of human phospholipase A2 enzymes

  摘要：

  A variety of 2-oxoamides and related amides based on natural and non-natural amino acids were synthesized. Their activity on two human intracellular phospholipases (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase (GV sPLA(2)) was evaluated. We show that an amide based on (R)-gamma-norleucine is a highly selective inhibitor of GV sPLA2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.046
• 作为产物：
  描述：

  7-苯基-1-庚醇 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 27.0h， 生成 2-hydroxy-8-phenyloctanenitrile
  参考文献：
  名称：

  ALPHA-KETOAMIDE DERIVATIVES USEFUL ENDOTHELIAL LIPASE INHIBITORS

  摘要：

  本发明涉及α-酮酰胺衍生物，含有它们的药物组合物以及它们在治疗受内皮脂酶调节的疾病和症状中的用途，例如心血管疾病。

  公开号：

  US20120077847A1

文献信息

• α-ketoamide derivatives useful endothelial lipase inhibitors
  申请人：Greco Michael N.

  公开号：US08476302B2

  公开（公告）日：2013-07-02

  The present invention is directed to α-ketoamide derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by endothelial lipase, for example, cardiovascular disorders.

  本发明涉及α-酮酰胺衍生物，包含它们的药物组合物以及它们在治疗受内皮酯酶调节的疾病和病状中的应用，例如心血管疾病。
• Comprehensive Analysis of Structure–Activity Relationships of α-Ketoheterocycles as <i>sn</i>-1-Diacylglycerol Lipase α Inhibitors
  作者：Freek J. Janssen、Marc P. Baggelaar、Jessica J. A. Hummel、Herman S. Overkleeft、Benjamin F. Cravatt、Dale L. Boger、Mario van der Stelt

  DOI：10.1021/acs.jmedchem.5b01627

  日期：2015.12.24

  Diacylglycerol lipase alpha (DAGL alpha) is responsible for the formation of the endocannabinoid 2-arachidonoylglycerol (2-AG) in the central nervous system. DAGL alpha inhibitors are required to study the physiological mile of 2-AG. Previously, we identified the alpha-ketoheterocycles as potent and highly selective DAGL alpha inhibitors. Here, we present the first comprehensive structure activity relationship study Of alpha-ketohetero cycles as DAGL alpha inhibitors. Our findings indicate that the active site, of DAGL alpha is remarkably sensitive to the type of heterocyclic scaffold with oxazolo-4N-pridines as the most active framework We uncovered a fundamental substituent effect in which electron-withdrawing meta-oxazole substituents increased inhibitor potency. (C-6-C-9)-iacyl chains with a distal phenyl group proved to be the most potent inhibitors. The integrated SAR data was consistent with the proposed binding pose in a DAGL alpha homology model. Altogether, our results may guide the design of future DAGL alpha inhibitors as leads for molecular therapies to treat neuroinflammation, obesity, and related metabolic disorders.
• US8476302B2
  申请人：——

  公开号：US8476302B2

  公开（公告）日：2013-07-02
• [EN] ALPHA-KETOAMIDE DERIVATIVES USEFUL ENDOTHELIAL LIPASE INHIBITORS<br/>[FR] DÉRIVÉS ALPHA-CÉTOAMIDE UTILES COMME INHIBITEURS DE LIPASE ENDOTHÉLIALE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2012047580A1

  公开（公告）日：2012-04-12

  The present invention is directed to α-ketoamide derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by endothelial lipase, for example, cardiovascular disorders.
• ALPHA-KETOAMIDE DERIVATIVES USEFUL ENDOTHELIAL LIPASE INHIBITORS
  申请人：Greco Michael N.

  公开号：US20120077847A1

  公开（公告）日：2012-03-29

  The present invention is directed to α-ketoamide derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by endothelial lipase, for example, cardiovascular disorders.

  本发明涉及α-酮酰胺衍生物，含有它们的药物组合物以及它们在治疗受内皮脂酶调节的疾病和症状中的用途，例如心血管疾病。