(±)-methyl 2-(3-methyl-4-nitrophenyl)propanoate | 83528-09-0

• 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: (±)-methyl 2-(3-methyl-4-nitrophenyl)propanoate
• 英文别名: Methyl 2-(3-methyl-4-nitrophenyl)propanoate
• CAS: 83528-09-0
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: LVHRYIRYGANAMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-methyl 2-(3-methyl-4-nitrophenyl)propanoate 在 盐酸 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 水 、 甲酸铵 、 palladium diacetate 、 potassium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙二醇甲醚 、 水 、 乙腈 为溶剂， 反应 82.5h， 生成 (±)-2-[4-[3-(hexylcarbamoyloxy)phenyl]-3-methylphenyl]propanoic acid
  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
• 作为产物：
  描述：

  5-氯-2-硝基甲苯 在 sodium hydroxide 、 硫酸 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.33h， 生成 (±)-methyl 2-(3-methyl-4-nitrophenyl)propanoate
  参考文献：
  名称：

  非甾体抗炎药。2。[（杂芳基氨基）苯基]链烷酸。

  摘要：

  制备了具有吡啶，喹啉或嘧啶作为杂芳基部分的一系列[（杂芳基氨基）苯基]链烷酸作为潜在的抗炎剂。其中，2- [4-（2-吡啶基氨基）苯基]丙酸（14b）具有出色的抗炎和镇痛活性，较少引起胃副反应。讨论了构效关系。

  DOI：

  10.1021/jm00356a019

文献信息

• HINO, KATSUHIKO;NAKAMURA, HIDEO;NAGAI, YASUTAKA;UNO, HITOSHI;NISHIMURA, H+, J. MED. CHEM., 1983, 26, N 2, 222-226
  作者：HINO, KATSUHIKO、NAKAMURA, HIDEO、NAGAI, YASUTAKA、UNO, HITOSHI、NISHIMURA, H+

  DOI：——

  日期：——