(4-bromophenyl) 5-(methoxyiminomethyl)-3,6-dihydro-2H-pyridine-1-carboxylate | 145071-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-bromophenyl) 5-(methoxyiminomethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 145071-46-1
• 化学式: C₁₄H₁₅BrN₂O₃
• 分子量: 339.189
• InChiKey: MHBMDVMWOYBAFW-UHFFFAOYSA-N

物化性质

• 沸点：
  431.5±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对溴氯甲酸苯酯 、 1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime hydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到(4-bromophenyl) 5-(methoxyiminomethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  1-substituted-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyloximes as novel orally active and long-lasting muscarinic cholinergic agonists

  摘要：

  Our previous attempts to design muscarinic agonists related to arecoline with the prerequisites for clinical use were successful with the discovery of 1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime hydrochloride, RU 35963, and structurally related compounds, in which die metabolically labile ester group of arecoline was replaced with the bioisosteric and stable aldoxime group. With the aim of obtaining compounds with improved cholinomimetic properties, several aryl- and alkyl-carbamates of RU 35963, as well as O-alkyl-, and O-aryl-carbamates of the 1-hydroxy-1,2,5,6-tetrahydropyridine-3- carboxaldehyde-O-methyloxime hydrochloride, 24, have been synthesized and evaluated biologically. The most interesting molecules to emerge from the primary screening have been evaluated more extensively and their cholinomimetic profiles compared with those of the parent molecules. In vitro studies indicate that none of these prodrugs have affinity for muscarinic receptor sites and some of them (aryl-carbamates) have cholinesterase inhibiting properties. Results from in vivo experiments in mice and rats showed that these new substances, 1-[4-chlorophenyl] oxycarbonyl-1,2,5,6-tetrahydropyridine-3- carboxaldehyde-O-methyloxime (16 = RU 47213) in particular, have cholinomimetic properties that compare favourably with those of the parent compounds. After oral administration 16 was clearly superior to RU 35963 in terms of central selectivity, duration of action and therapeutic indexes.

  DOI：

  10.1016/0223-5234(92)90186-5