benzyl 2-(9-acetyl-6-chloro-9H-carbazol-2-yl)propanoate | 1402840-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: benzyl 2-(9-acetyl-6-chloro-9H-carbazol-2-yl)propanoate
• 英文别名: Benzyl 2-(9-acetyl-6-chlorocarbazol-2-yl)propanoate；benzyl 2-(9-acetyl-6-chlorocarbazol-2-yl)propanoate
• CAS: 1402840-55-4
• 化学式: C₂₄H₂₀ClNO₃
• 分子量: 405.881
• InChiKey: HGRFJQIEUCLWAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-(9-acetyl-6-chloro-9H-carbazol-2-yl)propanoate 在 1% Pd on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 以19%的产率得到2-(9-acetyl-6-chloro-9H-carbazol-2-yl)propanoic acid
  参考文献：
  名称：

  Identification and Characterization of Carprofen as a Multitarget Fatty Acid Amide Hydrolase/Cyclooxygenase Inhibitor

  摘要：

  Pain and inflammation are major therapeutic areas for drug discovery. Current drugs for these pathologies have limited efficacy, however, and often cause a number of unwanted side effects. In the present study, we identify the nonsteroidal anti-inflammatory drug carprofen as a multitarget-directed ligand that simultaneously inhibits cyclooxygenase-1 (COX-1), COX-2, and fatty acid amide hydrolase (FAAH). Additionally, we synthesized and tested several derivatives of carprofen, sharing this multitarget activity. This may result in improved analgesic efficacy and reduced side effects (Naidu et al. J. Pharmacol. Exp. Ther. 2009, 329, 48-56; Fowler, C. J.; et al. J. Enzyme Inhib. Med. Chem. 2012, in press; Sasso et al. Pharmacol. Res. 2012, 65, 553). The new compounds are among the most potent multitarget FAAH/COX inhibitors reported so far in the literature and thus may represent promising starting points for the discovery of new analgesic and anti-inflammatory drugs.

  DOI：

  10.1021/jm3011146
• 作为产物：
  描述：

  卡洛芬 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.5h， 生成 benzyl 2-(9-acetyl-6-chloro-9H-carbazol-2-yl)propanoate
  参考文献：
  名称：

  Identification and Characterization of Carprofen as a Multitarget Fatty Acid Amide Hydrolase/Cyclooxygenase Inhibitor

  摘要：

  Pain and inflammation are major therapeutic areas for drug discovery. Current drugs for these pathologies have limited efficacy, however, and often cause a number of unwanted side effects. In the present study, we identify the nonsteroidal anti-inflammatory drug carprofen as a multitarget-directed ligand that simultaneously inhibits cyclooxygenase-1 (COX-1), COX-2, and fatty acid amide hydrolase (FAAH). Additionally, we synthesized and tested several derivatives of carprofen, sharing this multitarget activity. This may result in improved analgesic efficacy and reduced side effects (Naidu et al. J. Pharmacol. Exp. Ther. 2009, 329, 48-56; Fowler, C. J.; et al. J. Enzyme Inhib. Med. Chem. 2012, in press; Sasso et al. Pharmacol. Res. 2012, 65, 553). The new compounds are among the most potent multitarget FAAH/COX inhibitors reported so far in the literature and thus may represent promising starting points for the discovery of new analgesic and anti-inflammatory drugs.

  DOI：

  10.1021/jm3011146