3-(1-氧代丙基)-3,9-二氮杂双环[3.3.1]壬烷 | 328899-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 3-(1-氧代丙基)-3,9-二氮杂双环[3.3.1]壬烷
• 中文别名: 膦酸,[(环戊基氨基)羰基]-(9CI)
• 英文名称: N-39-propionyl-3,9-diazabicyclo[3.3.1]nonane
• 英文别名: 1-(3,9-Diazabicyclo[3.3.1]nonan-3-yl)propan-1-one
• CAS: 328899-05-4
• 化学式: C₁₀H₁₈N₂O
• 分子量: 182.266
• InChiKey: KBQNGHUIYSTQKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-氧代丙基)-3,9-二氮杂双环[3.3.1]壬烷 、 (E)-1-bromo-3-phenyl-2-butene 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以50%的产率得到9-[(2E)-3-phenylbut-2-enyl]-3-propionyl-3,9-diazabicyclo[3.3.1]nonane
  参考文献：
  名称：

  N-3(9)-Arylpropenyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes as μ-Opioid receptor agonists. Effects on μ-Affinity of arylalkenyl chain modifications

  摘要：

  Two series of N-3-arylpropenyl-N-9-propionyl-3,9-diazabicyclo[3.3.1]nonanes (1b-j) and of the reverted N-3-propionyl-N-9-arylpropenyl isomers (2b-j) as analogues of the previously reported analgesic N-3(9)-cinnamyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes (DBN) (1a, 2a) were synthesised and their affinity and selectivity towards opioid mu-, delta- and K-receptors were evaluated. Several compounds (1e,i.j 2d,e,f,g,j) exhibited a p-affinity in the low nanomolar range with moderate or negligible affinity towards delta- and kappa-receptors. The representative term N-9-(3,3-diphonylprop-2-enyl)-N-3-propionyl-DBN (2d) displayed in vivo (mouse) a potent analgesic effect (ED50 3.88 mg/kg ip) which favourably compared with that of morphine (ED50 5 mg/kg ip). In addition, 2d produced in mice tolerance after a period twice as long with morphine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00436-9

文献信息

• 3,9-Diazabicyclo[3.3.1]nonane derivatives with analgesic activity
  申请人：——

  公开号：US20030195217A1

  公开（公告）日：2003-10-16

  Compounds of formula (I) wherein R and R 1 , which are different from each other, are a straight or branched C 2 -C 8 acyl group, have analgesic activity.

  式（I）化合物，其中 R 和 R 1 互不相同，是直链或支链 C 2 -C 8酰基，具有镇痛活性。
• N-3(9)-Arylpropenyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes as μ-Opioid receptor agonists. Effects on μ-Affinity of arylalkenyl chain modifications
  作者：G Pinna

  DOI：10.1016/s0968-0896(01)00436-9

  日期：2002.6

  Two series of N-3-arylpropenyl-N-9-propionyl-3,9-diazabicyclo[3.3.1]nonanes (1b-j) and of the reverted N-3-propionyl-N-9-arylpropenyl isomers (2b-j) as analogues of the previously reported analgesic N-3(9)-cinnamyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes (DBN) (1a, 2a) were synthesised and their affinity and selectivity towards opioid mu-, delta- and K-receptors were evaluated. Several compounds (1e,i.j 2d,e,f,g,j) exhibited a p-affinity in the low nanomolar range with moderate or negligible affinity towards delta- and kappa-receptors. The representative term N-9-(3,3-diphonylprop-2-enyl)-N-3-propionyl-DBN (2d) displayed in vivo (mouse) a potent analgesic effect (ED50 3.88 mg/kg ip) which favourably compared with that of morphine (ED50 5 mg/kg ip). In addition, 2d produced in mice tolerance after a period twice as long with morphine. (C) 2002 Elsevier Science Ltd. All rights reserved.