tert-butyl 4-(1-methyl-2-oxo-1,2-dihydropyridine-4-carbonyl)piperidine-1-carboxylate | 1352725-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl 4-(1-methyl-2-oxo-1,2-dihydropyridine-4-carbonyl)piperidine-1-carboxylate
• 英文别名: Tert-butyl 4-(1-methyl-2-oxopyridine-4-carbonyl)piperidine-1-carboxylate
• CAS: 1352725-43-9
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: BSIMVHSTUSTMLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(1-methyl-2-oxo-1,2-dihydropyridine-4-carbonyl)piperidine-1-carboxylate 在 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 40.0h， 生成 4-(1-(3-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)piperidine-4-carbonyl)-1-methylpyridin-2(1H)-one oxalate
  参考文献：
  名称：

  Heteroaromatic and Aniline Derivatives of Piperidines As Potent Ligands for Vesicular Acetylcholine Transporter

  摘要：

  To identify suitable lipophilic compounds having high potency and selectivity for vesicular acetylcholine transporter (VAChT), a heteroaromatic ring or a phenyl group was introduced into the carbonyl-containing scaffold for VAChT ligands. Twenty new compounds with ALogD values between 0.53 and 3.2 were synthesized, and their in vitro binding affinities were assayed. Six of them (19a, 19e, 19g, 19k, and 24a-b) displayed high affinity for VAChT (K-i = 0.93-18 nM for racemates) and moderate to high selectivity for VAChT over sigma(1) and sigma(2) receptors (K-i = 44-4400-fold). These compounds have a methyl or a fluoro substitution that provides the position for incorporating PET radioisotopes C-11 or F-18. Compound (-)-[C-11]24b (K-i = 0.78 nM for VAChT, 1200-fold over sigma receptors) was successfully synthesized and evaluated in vivo in rats and nonhuman primates. The data revealed that (-)-[C-11]24b has highest binding in striatum and has favorable pharmacokinetics in the brain.

  DOI：

  10.1021/jm400664x
• 作为产物：
  描述：

  4-溴-1-甲基吡啶-2-酮 以38%的产率得到tert-butyl 4-(1-methyl-2-oxo-1,2-dihydropyridine-4-carbonyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Compounds comprising 4-benzoylpiperidine as a Sigma-1-selective ligand

  摘要：

  双哌啶基化合物及其盐被披露。这些化合物包括对σ1受体具有高亲和力的配体。一些化合物相对于σ2受体也具有高选择性。化合物可以包含放射性同位素，包括18F或11C。放射标记的化合物可用作探针，用于通过正电子发射断层扫描（PET扫描）在受试者（如人类）中成像σ1受体的分布。

  公开号：

  US20110311447A1