N-(3,4,5-trimethoxybenzoyl)isoquinuclidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(3,4,5-trimethoxybenzoyl)isoquinuclidine
• 英文别名: 2-Azabicyclo[2.2.2]octan-2-yl-(3,4,5-trimethoxyphenyl)methanone
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: UZAQMZPZVFGDGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-异喹宁酮 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(3,4,5-trimethoxybenzoyl)isoquinuclidine
  参考文献：
  名称：

  Isoquinuclidine-based expectorants. Synthesis and biological activities of N-alkoxybenzylisoquinuclidines

  摘要：

  N-Di-, trialkoxybenzylisoquinuclidines and related compounds were synthesized and evaluated for expectorant activities. Structure-activity relationship investigations in this series showed that both the trialkoxyphenyl ring and the basic nitrogen atom at the benzylic position were necessary for activity. N-Trialkoxybenzylisoquinuclidines 7a, 7c, 7d, 7f and 7g significantly increased bronchial secretion, and ethoxy derivative 7c showed the highest activity in these compounds. The n-propyloxy derivatives 7d and 7f also accelerated bronchoalveolar surfactant secretion with about two to four times more activity than ambroxol (7d and 7f; ED50 = 27.5 and 15.5 mg/kg po, respectively); however, compounds 7a, 7c and 7g were less active than ambroxol. Compounds 7d and 7f were selected for further examination. These compounds displayed antioxidant activity in vitro (7d and 7f, IC50 = 48.0 and 66.0 mu M, respectively). Compound 7d also showed inhibition on bradykinin- or antigen-induced airway inflammation in guinea pigs. These findings suggest that compounds 7d and 7f are potent expectorants with antiinflammatory activity.

  DOI：

  10.1016/s0223-5234(97)81675-3