(RS)-1,6-dimethyl-3-(ethoxycarbonyl)-1,2,5,6-tetrahydropyridine oxalate | 131041-94-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (RS)-1,6-dimethyl-3-(ethoxycarbonyl)-1,2,5,6-tetrahydropyridine oxalate
• 英文别名: methyl 1,6-dimethyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrogen oxalate；methyl 1,2-dimethyl-3,6-dihydro-2H-pyridine-5-carboxylate;oxalic acid
• CAS: 131041-94-6
• 化学式: C₂H₂O₄*C₉H₁₅NO₂
• 分子量: 259.259
• InChiKey: OSRXBYHRIZKFAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  104.14
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (RS)-1,6-dimethyl-3-(ethoxycarbonyl)-1,2,5,6-tetrahydropyridine oxalate 、 氯甲酸乙烯酯 以82%的产率得到
  参考文献：
  名称：

  SHOWELL, GRAHAM A.;GIBBONS, TRACEY L.;KNEEN, CLARE O.;MACLEOD, ANGUS M.;M+, J. MED. CHEM., 34,(1991) N, C. 1086-1094

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 6-methylnicotinate methiodide 、 草酸 、 硼氢化钠 、 乙醇 、 水 以69%的产率得到
  参考文献：
  名称：

  SHOWELL, GRAHAM A.;GIBBONS, TRACEY L.;KNEEN, CLARE O.;MACLEOD, ANGUS M.;M+, J. MED. CHEM., 34,(1991) N, C. 1086-1094

  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.