3-[3-(2-naphthalenyl)-1,2,4-oxadiazol-5-yl]-1-azabicyclo[2.2.2]octane | 131012-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[3-(2-naphthalenyl)-1,2,4-oxadiazol-5-yl]-1-azabicyclo[2.2.2]octane
• 英文别名: 5-(1-Azabicyclo[2.2.2]octan-3-yl)-3-naphthalen-2-yl-1,2,4-oxadiazole
• CAS: 131012-90-3
• 化学式: C₁₉H₁₉N₃O
• 分子量: 305.379
• InChiKey: FGHRIQKCMVNGAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-氮杂双环[2.2.2]辛烷-3-羧酸甲酯 、 N’-羟基-2-萘甲脒 在 4 A molecular sieve 、 sodium hydride 作用下， 生成 3-[3-(2-naphthalenyl)-1,2,4-oxadiazol-5-yl]-1-azabicyclo[2.2.2]octane
  参考文献：
  名称：

  Novel 5-HT3 antagonists. Indole oxadiazoles

  摘要：

  The synthesis and biochemical evaluation of a series of indole oxadiazole 5-HT3 antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while two hydrogen-bonding interactions are possible, only one is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 angstrom and the steric limitations are defined by van der Waals difference mapping.

  DOI：

  10.1021/jm00105a021

文献信息

• US5135935A
  申请人：——

  公开号：US5135935A

  公开（公告）日：1992-08-04
• Novel 5-HT3 antagonists. Indole oxadiazoles
  作者：C. J. Swain、R. Baker、C. Kneen、J. Moseley、J. Saunders、E. M. Seward、G. Stevenson、M. Beer、J. Stanton、K. Watling

  DOI：10.1021/jm00105a021

  日期：1991.1

  The synthesis and biochemical evaluation of a series of indole oxadiazole 5-HT3 antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while two hydrogen-bonding interactions are possible, only one is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 angstrom and the steric limitations are defined by van der Waals difference mapping.