[3-[2-fluoro-4-(2-hydroxy-1-methyl-ethyl)phenyl]phenyl] N-hexylcarbamate | 1557066-60-0

• 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: [3-[2-fluoro-4-(2-hydroxy-1-methyl-ethyl)phenyl]phenyl] N-hexylcarbamate
• 英文别名: [3-[2-fluoro-4-(2-hydroxy-1-methyl-ethyl)phenyl]phenyl]N-hexylcarbamate；[3-[2-fluoro-4-(1-hydroxypropan-2-yl)phenyl]phenyl] N-hexylcarbamate
• CAS: 1557066-60-0
• 化学式: C₂₂H₂₈FNO₃
• 分子量: 373.468
• InChiKey: WGAHHJUZFSFTHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (±)-methyl 2-(4-nitro-3-fluorophenyl)propanoate 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 甲酸铵 、 palladium diacetate 、 氯化锆(IV) 、 potassium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇甲醚 、 水 、 乙腈 为溶剂， 反应 35.5h， 生成 [3-[2-fluoro-4-(2-hydroxy-1-methyl-ethyl)phenyl]phenyl] N-hexylcarbamate
  参考文献：
  名称：

  Potent multitarget FAAH-COX inhibitors: Design and structure-activity relationship studies

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) exert their pharmacological effects by inhibiting cyclooxygenase (COX)-1 and COX-2. Though widely prescribed for pain and inflammation, these agents have limited utility in chronic diseases due to serious mechanism-based adverse events such as gastrointestinal damage. Concomitant blockade of fatty acid amide hydrolase (FAAH) enhances the therapeutic effects of the NSAIDs while attenuating their propensity to cause gastrointestinal injury. This favorable interaction is attributed to the accumulation of protective FAAH substrates, such as the endocannabinoid anandamide, and suggests that agents simultaneously targeting COX and FAAH might provide an innovative strategy to combat pain and inflammation with reduced side effects. Here, we describe the rational design and structure-active relationship (SAR) properties of the first class of potent multitarget FAAH-COX inhibitors. A focused SAR exploration around the prototype 10r (ARN2508) led to the identification of achiral (18b) as well as racemic (29a-c and 29e) analogs. Absolute configurational assignment and pharmacological evaluation of single enantiomers of 10r are also presented. (S)-(+)-10r is the first highly potent and selective chiral inhibitor of FAAH-COX with marked in vivo activity, and represents a promising lead to discover novel analgesics and anti-inflammatory drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.036
• 作为试剂：
  描述：

  异氰酸己酯 、 3-[2-fluoro-4-(2-hydroxy-1-methyl-ethyl)phenyl]phenol 在 [3-[2-fluoro-4-(2-hydroxy-1-methyl-ethyl)phenyl]phenyl] N-hexylcarbamate 、 乙酸乙酯 作用下， 以to afford the title compound as a colorless oil (137 mg, 73%)的产率得到[3-[2-fluoro-4-(2-hydroxy-1-methyl-ethyl)phenyl]phenyl] N-hexylcarbamate
  参考文献：
  名称：

  MULTITARGET FAAH AND COX INHIBITORS AND THERAPEUTICAL USES THEREOF

  摘要：

  多靶点抑制剂，包括脂肪酸酰胺水解酶（FAAH）、环氧合酶-1（COX-1）和/或环氧合酶-2（COX-2），其在取代联苯核心的A环的间位或邻位具有特定的氨基甲酸酯基团，并且在联苯核心的B环的邻位具有卤素。此外，还涉及多靶点抑制剂的治疗应用，特别是在癌症的预防和治疗方面。

  公开号：

  US20150203447A1

文献信息

• US9630914B2
  申请人：——

  公开号：US9630914B2

  公开（公告）日：2017-04-25