9-(benzo[1,3]dioxol-5-yl)-1,2,3,4,5,6-hexahydro-1,5-methano-pyridino[1,2-a]diazocin-8-one

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: 9-(benzo[1,3]dioxol-5-yl)-1,2,3,4,5,6-hexahydro-1,5-methano-pyridino[1,2-a]diazocin-8-one
• 英文别名: (1R,9S)-5-(1,3-benzodioxol-5-yl)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: ATFUSKXJETVOBY-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cytisine 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 9-(benzo[1,3]dioxol-5-yl)-1,2,3,4,5,6-hexahydro-1,5-methano-pyridino[1,2-a]diazocin-8-one
  参考文献：
  名称：

  The 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor ligands. Part 2: Carboxamide derivatives with different spacer motifs

  摘要：

  3,7-Diazabicyclo[3.3.1]nonane (bispidine) based nicotinic acetylcholine receptor (nAChR) ligands have been synthesized and evaluated for nAChRs interaction. Diverse spacer motifs were incorporated between the hydrogen bond acceptor (HBA) part and a variety of substituted (hetero)aryl moieties. Bispidine carboxamides bearing spacer motifs often showed high affinity in the low nanomolar range and selectivity for the alpha 4 beta 2* nAChR. Compounds 15, 25, and 47 with K-i values of about 1 nM displayed the highest affinities for alpha 4 beta 2* nAChR. All evaluated compounds are partial agonists or antagonists at alpha 4 beta 2*, with reduced or no effects on alpha 3 beta 4* with the exception of compound 15 (agonist), and reduced or no effect at alpha 7 and muscle subtypes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.060