1-ethyl-1,2,5.6-tetrahydro-3-(methoxycarbonyl)pyridinium chloride | 114878-44-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 1-ethyl-1,2,5.6-tetrahydro-3-(methoxycarbonyl)pyridinium chloride
• 英文别名: N-ethyl arecoline monohydrochloride；1-ethyl-3-methoxycarbonyl-1,2,5,6-tetrahydropyridinium chloride；hydron;methyl 1-ethyl-3,6-dihydro-2H-pyridine-5-carboxylate;chloride
• CAS: 114878-44-3
• 化学式: C₉H₁₅NO₂*ClH
• 分子量: 205.685
• InChiKey: RVIFACSYNHMHAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-羟基戊脒 、 1-ethyl-1,2,5.6-tetrahydro-3-(methoxycarbonyl)pyridinium chloride 在 4 A molecular sieve 、 sodium 作用下， 生成 3-(3-butyl-1,2,4-oxadiazol-5-yl)-1-ethyl-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00106a033

文献信息

• Piperidine compounds and their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0259621A2

  公开（公告）日：1988-03-16

  New piperidine compounds having the formula wherein at least one of R³, R⁴, and R⁵ are and the other independently are H or C1-6-alkyl, wherein Rʹ is H, C1-8-alkyl, phenyl, thienyl, cyclopropyl, or C1-3-alkoxymethyl; and R¹ and R⁶ independently are H or C1-6-alkyl and a salt thereof with a pharmaceutically-acceptable acid. The new compounds are useful in improving the cognitive functions of the forebrain and hippocampus of mammals, and are useful in the treatment of Alzheimer's disease.

  具有以下式子的新哌啶化合物 式中 R³、R⁴ 和 R⁵ 中至少有一个是 和 R⁵ 中至少有一个是 H 或 C1-6-烷基、 其中 Rʹ 是 H、C1-8-烷基、苯基、噻吩基、环丙基或 C1-3- 烷氧基甲基；以及 R¹和 R⁶各自为 H 或 C1-6- 烷基 及其与药学上可接受的酸的盐。 新化合物有助于改善哺乳动物前脑和海马的认知功能，并可用于治疗阿尔茨海默氏症。
• US4837241A
  申请人：——

  公开号：US4837241A

  公开（公告）日：1989-06-06
• US4933353A
  申请人：——

  公开号：US4933353A

  公开（公告）日：1990-06-12