(2β,9aα)-4-amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide | 98482-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (2β,9aα)-4-amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide
• 英文别名: N-[(2R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-2-yl]-4-amino-5-chloro-2-methoxybenzamide
• CAS: 98482-28-1
• 化学式: C₁₇H₂₄ClN₃O₂
• 分子量: 337.849
• InChiKey: XCRYPPFCGUXBDD-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  67.59
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2β,9aα)-4-amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Novel quinolizidine salicylamide influenza fusion inhibitors

  摘要：

  A novel series of quinolizidine salicylamides was synthesized as specific inhibitors of the H1 subtype of influenza A viruses. These inhibitors inhibit the pH-induced fusion process, thereby blocking viral entry into host cells. Compound 16 was the most active inhibitor in this series with an EC50 of 0.25 mu g/mL in plaque reduction assay. The synthesis and the SAR of these compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00361-3
• 作为产物：
  描述：

  (2R,9aR)-2-Azido-octahydro-quinolizine 在 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 生成 (2β,9aα)-4-amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide
  参考文献：
  名称：

  Novel quinolizidine salicylamide influenza fusion inhibitors

  摘要：

  A novel series of quinolizidine salicylamides was synthesized as specific inhibitors of the H1 subtype of influenza A viruses. These inhibitors inhibit the pH-induced fusion process, thereby blocking viral entry into host cells. Compound 16 was the most active inhibitor in this series with an EC50 of 0.25 mu g/mL in plaque reduction assay. The synthesis and the SAR of these compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00361-3

文献信息

• Substituted benzamides with conformationally restricted side chains. 1. Quinolizidine derivatives as selective gastric prokinetic agents
  作者：Michael S. Hadley、Frank D. King、Brian McRitchie、David H. Turner、Eric A. Watts

  DOI：10.1021/jm00150a015

  日期：1985.12

  ring retain gastric activity. Of these 2-substituted compounds, the 2 alpha, 9a alpha isomer has potent selective gastric prokinetic activity with only weak dopamine antagonist properties. Spectroscopic data show that the quinolizidine ring preferentially adopts a trans chair-chair conformation with an axial benzamide moiety. However, energy calculations indicate that, at nondopaminergic receptors controlling

  甲氧氯普胺的胃促运动作用可能主要不是由于其多巴胺拮抗剂活性。本发明的目的是通过构象限制胃复安的侧链来获得缺乏多巴胺拮抗剂活性的选择性胃动力药。在一系列喹oli嗪基苯甲酰胺中，只有在喹oli啶环的2位具有苯甲酰胺部分的化合物才能保持胃活性。在这些2-取代的化合物中，2α，9aα异构体具有有效的选择性胃促胃功能，仅具有弱的多巴胺拮抗剂性质。光谱数据表明，喹喔啉环优先采用具有轴向苯甲酰胺部分的反式-椅构象。但是，能量计算表明，在控制胃动力的非多巴胺能受体上，
• HADLEY, M. S.;KING, F. D.;MCRITCHIE, B.;TURNER, D. H.;WATTS, E. A., J. MED. CHEM., 1985, 28, N 12, 1843-1847
  作者：HADLEY, M. S.、KING, F. D.、MCRITCHIE, B.、TURNER, D. H.、WATTS, E. A.

  DOI：——

  日期：——