8-methyl-8-azabicyclo[3,2,1]octan-3-yl 6-methoxy-2-naphthylacetate methiodide (21) | 1092719-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-methyl-8-azabicyclo[3,2,1]octan-3-yl 6-methoxy-2-naphthylacetate methiodide (21)
• CAS: 1092719-64-6
• 化学式: C₂₂H₂₈NO₃*I
• 分子量: 481.374
• InChiKey: BHPUWZOZKOURTR-CVUDIUBKSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(6-methoxynaphthalen-2-yl)acetate 、 碘甲烷 以 异丙醚 为溶剂， 反应 0.5h， 以78%的产率得到8-methyl-8-azabicyclo[3,2,1]octan-3-yl 6-methoxy-2-naphthylacetate methiodide (21)
  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