5,8,9,10,11,11a-hexahydro-6H-pyrido[1,2-h]-1,7-naphthyridine | 112114-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,8,9,10,11,11a-hexahydro-6H-pyrido[1,2-h]-1,7-naphthyridine
• 英文别名: 5,6,7,8,9,10-Hexahydro-4bH-4,8a-diaza-phenanthrene；6,8,9,10,11,11a-hexahydro-5H-pyrido[1,2-h][1,7]naphthyridine
• CAS: 112114-03-1
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: JWBLYAGFFUSJCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 1-oxooctahydro-1H-quinolizine-2-carboxylate 在 盐酸羟胺 、 水 、 sodium hydride 、 lithium chloride 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 32.0h， 生成 5,8,9,10,11,11a-hexahydro-6H-pyrido[1,2-h]-1,7-naphthyridine
  参考文献：
  名称：

  Structure-affinity relationships of arylquinolizines at .alpha.-adrenoceptors

  摘要：

  Hexahydroaryl[a]quinolizines comprise a prominent structural element in several alpha 2-adrenoceptor antagonists. Eight hexahydroheteroarylquinolizines were prepared as minimal ligands to investigate the relationship between the nature of the aromatic ring and affinity of these molecules for alpha-adrenoceptors. Affinity for alpha 1-and alpha 2-adrenoceptors was assessed by displacement of [3H]prasozin and [3H]clonidine, respectively. Lipophilicity of the aryl portion of the molecules, reflected by their partition coefficient between octanol and pH 7.4 buffer, correlated well with affinity at both receptor subtypes. Although some compounds showed nanomolar affinity for alpha-adrenoceptors, no subtype selectivity was observed. These results suggest that the aromatic ring enhances binding at both receptors chiefly through hydrophobic interactions and contributes little to subtype selectivity.

  DOI：

  10.1021/jm00398a025

文献信息

• HUFF, JOEL R.;BALDWIN, JOHN J.;DESOLMS, S. JANE;GUARE, JAMES P. , JR.;HUN+, J. MED. CHEM., 31,(1988) N 3, 641-645
  作者：HUFF, JOEL R.、BALDWIN, JOHN J.、DESOLMS, S. JANE、GUARE, JAMES P. , JR.、HUN+

  DOI：——

  日期：——
• Structure-affinity relationships of arylquinolizines at .alpha.-adrenoceptors
  作者：Joel R. Huff、John J. Baldwin、S. Jane DeSolms、James P. Guare、Cecilia A. Hunt、William C. Randall、William S. Sanders、Steven J. Smith、Joseph P. Vacca、Matthew M. Zrada

  DOI：10.1021/jm00398a025

  日期：1988.3

  Hexahydroaryl[a]quinolizines comprise a prominent structural element in several alpha 2-adrenoceptor antagonists. Eight hexahydroheteroarylquinolizines were prepared as minimal ligands to investigate the relationship between the nature of the aromatic ring and affinity of these molecules for alpha-adrenoceptors. Affinity for alpha 1-and alpha 2-adrenoceptors was assessed by displacement of [3H]prasozin and [3H]clonidine, respectively. Lipophilicity of the aryl portion of the molecules, reflected by their partition coefficient between octanol and pH 7.4 buffer, correlated well with affinity at both receptor subtypes. Although some compounds showed nanomolar affinity for alpha-adrenoceptors, no subtype selectivity was observed. These results suggest that the aromatic ring enhances binding at both receptors chiefly through hydrophobic interactions and contributes little to subtype selectivity.