2-(3-butyl-1,2,4-oxadiazol-5-yl)-8-methyl-8-azabicyclo<3.2.1>oct-2-ene | 123686-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(3-butyl-1,2,4-oxadiazol-5-yl)-8-methyl-8-azabicyclo<3.2.1>oct-2-ene
• 英文别名: 3-Butyl-5-(8-methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl)-1,2,4-oxadiazole
• CAS: 123686-95-3
• 化学式: C₁₄H₂₁N₃O
• 分子量: 247.34
• InChiKey: HIHAAFSTCBQDDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  古卡因 、 N'-羟基戊脒 生成 2-(3-butyl-1,2,4-oxadiazol-5-yl)-8-methyl-8-azabicyclo<3.2.1>oct-2-ene
  参考文献：
  名称：

  SAUERBERG, PER;KINDTLER, JENS W.;NIELSEN, LONE;SHEARDOWN, MALCOLM J.;HONO+, J. MED. CHEM., 34,(1991) N, C. 687-692

  摘要：

  DOI：

文献信息

• Muscarinic cholinergic agonists and antagonists of the 3-(3-alkyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydropyridine type. Synthesis and structure-activity relationships
  作者：Per Sauerberg、Jens W. Kindtler、Lone Nielsen、Malcolm J. Sheardown、Tage Honore

  DOI：10.1021/jm00106a033

  日期：1991.2

  A series of 3-(3-alkyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydro-1-methylpyridines (2a-q) were synthesized and tested for central muscarinic cholinergic receptor binding affinity by using [H-3]oxotremorine-M and [H-3]QNB as ligands and in a functional assay using guinea pig ileum. The analogues with unbranched C1-8-alkyl substituents (2a-g) were agonist, whereas the compounds with branched or cyclic substituents (2h-m) were antagonists. The alkyl ether analogues (2o-q) were also agonists but had lower receptor binding affinity than the corresponding alkyl analogues. The 3-(5-alkyl-1,2,4-oxadiazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine analogues had only very low affinity for the central muscarinic receptors and were weak antagonists in the ileum assay. A few 3-(3-butyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydro-1-methylpyridines substituted with methyl or hydrogen in the 1-, 5-, or 6-position were synthesized and tested. N-Desmethyl analogue 7 was a potent muscarinic agonist, whereas N-desmethyl-5-methyl analogue 11 and N-methyl-6-methyl analogue 13 both were antagonists with lower muscarinic receptor affinity. The 3-(3-butyl-1,2,4-oxadiazol-5-yl)quinuclidine (17) and tropane (15) analogues were both very potent antagonists with high affinity for central muscarinic receptors. The ratio [IC50(QNB)/IC50(Oxo-M)] x 0.162 proved to be a good indicator of the efficacy of the compounds in the guinea pig ileum assay.
• SAUERBERG, PER;KINDTLER, JENS W.;NIELSEN, LONE;SHEARDOWN, MALCOLM J.;HONO+, J. MED. CHEM., 34,(1991) N, C. 687-692
  作者：SAUERBERG, PER、KINDTLER, JENS W.、NIELSEN, LONE、SHEARDOWN, MALCOLM J.、HONO+

  DOI：——

  日期：——