2-(4-Isobutyl-phenyl)-propionic acid (1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester | 155649-07-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 2-(4-Isobutyl-phenyl)-propionic acid (1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester
• CAS: 155649-07-3
• 化学式: C₂₁H₃₁NO₂
• 分子量: 329.483
• InChiKey: UZRZFHJTHKHIRC-DRYDUVHZSA-N

物化性质

• 沸点：
  418.0±40.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-Isobutyl-phenyl)-propionic acid (1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 、 碘甲烷 以 异丙醚 为溶剂， 反应 0.5h， 以83%的产率得到8-methyl-8-azabicyclo[3,2,1]octan-3-yl 2-(4-isobutylphenyl)propionate methiodide
  参考文献：
  名称：

  Site specific chemical delivery of NSAIDs to inflamed joints: Synthesis, biological activity and γ-imaging studies of quaternary ammonium salts of tropinol esters of some NSAIDs or their active metabolites

  摘要：

  Quaternized tropinol ester derivatives of some commonly used non-steroidal anti-inflammatory drugs (NSAIDs) or their active metabolites, were prepared and studied for their anti-inflammatory activity in a chronic inflammation model and for inflamed tissue tropism. The quaternized esters were radiolabeled with 99(m)Technetium (Tc-99m) and their selective localization in the inflamed tissue was traced using scintigraphy. In the chronic arthritis rodent model, most of the quaternized esters exhibited anti-inflammatory effect comparable to their respective parent drugs. In the gamma-imaging studies only the quaternary derivatives exhibited selective accumulation into the inflamed tissue unlike the parent NSAIDs or the unquaternized tropinol esters. This work is a step ahead in the direction of use of quaternary ammonium ester derivatives for site specific chemical delivery of commonly used NSAIDs to the inflamed tissues to minimize their GIT side effect or other systemic toxicities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.050
• 作为产物：
  描述：

  2-[4-(2-甲基丙基)苯基]乙酰氯 在 氢氧化钾 、 氯化亚砜 、 水 、 sodium amide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 40.83h， 生成 2-(4-Isobutyl-phenyl)-propionic acid (1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester
  参考文献：
  名称：

  突触前胆碱能调节剂可作为有效的认知增强剂和止痛药。1.热带和2-苯基丙酸酯。

  摘要：

  先前的研究表明，（R）-（+）-hyscyamine具有镇痛活性，这是由于中央毒蕈碱自体受体拮抗后ACh释放增加所致。由于增强中央胆碱能传递可能对认知障碍有益，因此我们操纵了（R）-（+）-水苏胺，合成了几种热带和2-苯基丙酸衍生物，目的是获得能够增加ACh释放的药物因此具有镇痛和促智作用。结果表明，几种新化合物确实是有效的镇痛药（镇痛作用与吗啡相当），并且最有效的一种（（+/-）-19，PG9）也具有显着的认知增强特性。

  DOI：

  10.1021/jm00037a022