N-allyl-3-deoxynormorphine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: N-allyl-3-deoxynormorphine
• 英文别名: MCL-400；(4R,4aR,7S,7aR,12bS)-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: RVRWQOSKMVZMOM-HZMZCJTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-allyl-3-deoxynormorphine 在 甲烷磺酸 作用下， 反应 0.5h， 生成 (R)-(-)-11-hydroxy-N-allylnoraporphine
  参考文献：
  名称：

  Synthesis and neuropharmacological evaluation of R(−)-N-alkyl-11-hydroxynoraporphines and their esters

  摘要：

  We synthesized several N-substituted-11-hydroxynoraporphines and their esters of varying chain length, evaluated their binding affinity at dopamine (DA) receptor sites in rat caudate-putamen membranes, and quantified their effects on motor activity in normal adult male rats. The 11-hydroxyaporphines showed similar neuropharmacological properties to the corresponding 10,11-catecholaporphines. At moderate doses, their esters proved to have more prolonged behavioral actions and superior oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.029
• 作为产物：
  描述：

  3-deoxynormorphine 、 alkaline earth salt of/the/ methylsulfuric acid 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 N-allyl-3-deoxynormorphine
  参考文献：
  名称：

  Synthesis and neuropharmacological evaluation of R(−)-N-alkyl-11-hydroxynoraporphines and their esters

  摘要：

  We synthesized several N-substituted-11-hydroxynoraporphines and their esters of varying chain length, evaluated their binding affinity at dopamine (DA) receptor sites in rat caudate-putamen membranes, and quantified their effects on motor activity in normal adult male rats. The 11-hydroxyaporphines showed similar neuropharmacological properties to the corresponding 10,11-catecholaporphines. At moderate doses, their esters proved to have more prolonged behavioral actions and superior oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.029

文献信息

• An investigation of the N-demethylation of 3-deoxymorphine and the affinity of the alkylation products to μ, δ, and κ receptors
  作者：Csaba Csutoras、Ao Zhang、Jean M Bidlack、John L Neumeyer

  DOI：10.1016/j.bmc.2004.03.011

  日期：2004.5

  The N-demethylation of 3-deoxymorphine (1) was investigated using methyl chloroformate and hydrazine. 3-Deoxynormorphine (2) was obtained in 70% yield, and 3-deoxydihydronormorphine (3) was also obtained as a side product. The mu, delta, and kappa receptor binding affinity of a series of N-substituted 3-deoxynormorphines 6 and 7 and N-substituted 3-deoxydihydronormorphines 8-11 was also determined. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and neuropharmacological evaluation of R(−)-N-alkyl-11-hydroxynoraporphines and their esters
  作者：Csaba Csutoras、Ao Zhang、Kehong Zhang、Nora S. Kula、Ross J. Baldessarini、John L. Neumeyer

  DOI：10.1016/j.bmc.2004.04.029

  日期：2004.7

  We synthesized several N-substituted-11-hydroxynoraporphines and their esters of varying chain length, evaluated their binding affinity at dopamine (DA) receptor sites in rat caudate-putamen membranes, and quantified their effects on motor activity in normal adult male rats. The 11-hydroxyaporphines showed similar neuropharmacological properties to the corresponding 10,11-catecholaporphines. At moderate doses, their esters proved to have more prolonged behavioral actions and superior oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.