meso-N-[(3-exo)-8-azabicyclo[3.2.1]oct-3-yl]acetamide hydrochloride | 91596-05-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: meso-N-[(3-exo)-8-azabicyclo[3.2.1]oct-3-yl]acetamide hydrochloride
• CAS: 91596-05-3
• 化学式: C₉H₁₆N₂O*ClH
• 分子量: 204.7
• InChiKey: NUHYOUQYLOXWOY-HGOFDQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  41.13
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-氯甲基吡啶盐酸盐 、 meso-N-[(3-exo)-8-azabicyclo[3.2.1]oct-3-yl]acetamide hydrochloride 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成 N-[8-(3-pyridylmethyl)-8-azabicyclo[3.2.1]oct-3β-yl]acetamide
  参考文献：
  名称：

  Synthesis and biological investigations of 3β-aminotropane arylamide derivatives with atypical antipsychotic profile

  摘要：

  This work is a continuation of our previous research, concentrating this time on lead structure modification to increase the 5-HT1A receptor affinity and water solubility of designed compounds. Therefore, the compounds synthesised within the present project included structural analogues of 3 beta-acylamine derivatives of tropane with the introduction of a methyl substituent in the benzyl ring and a 2-quinoline, 3-quinoline, or 6-quinoline moiety. A series of novel 3 beta-aminotropane derivatives was evaluated for their affinity for 5-HT1A, 5-HT2A, and D-2 receptors, which allowed for the identification of compounds 12e, 12i, and 19a as ligands with highest affinity for the tested receptors; they were then subjected to further evaluation in preliminary in vivo studies. Selected compounds 12i and 19a displayed antipsychotic properties in the d-amphetamine-induced and MK-801-induced hyperlocomotor activity test in mice. Moreover, compound 19a showed significant antidepressant-like activity in the forced swim test in mice.

  DOI：

  10.1007/s00044-018-2203-z
• 作为产物：
  描述：

  N-((1R,3s,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-3-yl)acetamide 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 生成 meso-N-[(3-exo)-8-azabicyclo[3.2.1]oct-3-yl]acetamide hydrochloride
  参考文献：
  名称：

  Synthesis and biological investigations of 3β-aminotropane arylamide derivatives with atypical antipsychotic profile

  摘要：

  This work is a continuation of our previous research, concentrating this time on lead structure modification to increase the 5-HT1A receptor affinity and water solubility of designed compounds. Therefore, the compounds synthesised within the present project included structural analogues of 3 beta-acylamine derivatives of tropane with the introduction of a methyl substituent in the benzyl ring and a 2-quinoline, 3-quinoline, or 6-quinoline moiety. A series of novel 3 beta-aminotropane derivatives was evaluated for their affinity for 5-HT1A, 5-HT2A, and D-2 receptors, which allowed for the identification of compounds 12e, 12i, and 19a as ligands with highest affinity for the tested receptors; they were then subjected to further evaluation in preliminary in vivo studies. Selected compounds 12i and 19a displayed antipsychotic properties in the d-amphetamine-induced and MK-801-induced hyperlocomotor activity test in mice. Moreover, compound 19a showed significant antidepressant-like activity in the forced swim test in mice.

  DOI：

  10.1007/s00044-018-2203-z