methyl 2-(4-(bromomethyl)-2-iodophenyl)propanoate | 1241405-34-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: methyl 2-(4-(bromomethyl)-2-iodophenyl)propanoate
• CAS: 1241405-34-4
• 化学式: C₁₁H₁₂BrIO₂
• 分子量: 383.024
• InChiKey: QLGFHRYXKYTFEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-(bromomethyl)-2-iodophenyl)propanoate 在 盐酸 、 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 sodium 2-{2-iodo-4-[(2-oxocyclopentyl)methyl]phenyl}propanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of loxoprofen derivatives

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory actions through an inhibitory effect on cyclooxygenase (COX). Two COX subtypes, COX-1 and COX-2, are responsible for the majority of COX activity at the gastrointestinal mucosa and in tissues with inflammation, respectively. We previously suggested that both gastric mucosal cell death due to the membrane permeabilization activity of NSAIDs and COX-inhibition at the gastric mucosa are involved in NSAID-induced gastric lesions. We have also reported that loxoprofen has the lowest membrane permeabilization activity among the NSAIDs we tested. In this study, we synthesized a series of loxoprofen derivatives and examined their membrane permeabilization activities and inhibitory effects on COX-1 and COX-2. Among these derivatives, 2-{4'-hydroxy-5-[(2-oxocyclopentyl)methyl]biphenyl-2-yl}propanoate 31 has a specificity for COX-2 over COX-1. Compared to loxoprofen, oral administration of 31 to rats produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 31 is likely to be a therapeutically beneficial and safer NSAID. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.050
• 作为产物：
  描述：

  3-碘-4-甲基苯胺 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 、 sodium acetate 、 双(三甲基硅烷基)氨基钾 、 copper(II) sulfate 、 高碘酸 、 sodium sulfite 、 lithium diisopropyl amide 、 sodium nitrite 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 生成 methyl 2-(4-(bromomethyl)-2-iodophenyl)propanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of loxoprofen derivatives

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory actions through an inhibitory effect on cyclooxygenase (COX). Two COX subtypes, COX-1 and COX-2, are responsible for the majority of COX activity at the gastrointestinal mucosa and in tissues with inflammation, respectively. We previously suggested that both gastric mucosal cell death due to the membrane permeabilization activity of NSAIDs and COX-inhibition at the gastric mucosa are involved in NSAID-induced gastric lesions. We have also reported that loxoprofen has the lowest membrane permeabilization activity among the NSAIDs we tested. In this study, we synthesized a series of loxoprofen derivatives and examined their membrane permeabilization activities and inhibitory effects on COX-1 and COX-2. Among these derivatives, 2-{4'-hydroxy-5-[(2-oxocyclopentyl)methyl]biphenyl-2-yl}propanoate 31 has a specificity for COX-2 over COX-1. Compared to loxoprofen, oral administration of 31 to rats produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 31 is likely to be a therapeutically beneficial and safer NSAID. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.050