(-)-5β-methyl-6-demethoxythebaine | 138188-26-8

• 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: (-)-5β-methyl-6-demethoxythebaine
• 英文别名: (4R,7aS,12bS)-9-methoxy-3,7a-dimethyl-1,2,4,13-tetrahydro-4,12-methanobenzofuro[3,2-e]isoquinoline
• CAS: 138188-26-8
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: CIBRMULRMQWAKS-CCKFTAQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-5β-methyl-6-demethoxythebaine 在 盐酸 、 甲烷磺酸 、 三氯化硼 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-methylapomorphine hydrochloride
  参考文献：
  名称：

  1-substituted apomorphines as potent dopamine agonists

  摘要：

  A novel set of 1-substituted apomorphines as dopaminergic agonists were synthesized according to our new strategy employing the acid-catalyzed rearrangement of diversely functionalized 5 beta-substituted-6-demethoxythebaines. The activities of new compounds for dopamine receptors subtypes were evaluated using HEK293 based stable cell lines expressing D-1, D-2L or D-3 receptor subtypes. All studied compounds had affinities in nanomolar range for D-2L and D-3 receptors and the change of the nature of substituent in position 1 had only moderate effect. D-1 receptors were sensitive to the introduction of the 4-OH-benzyl function resulting in an increased affinity. The small hydrophilic group (hydroxymethyl) highly reduced the agonist affinity and potency thereby increasing subtype selectivity. This strategy for selective modulation of affinities and potencies of 1-substituted apomorphines gives essential hints for future design of subtype selective dopaminergic ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.014
• 作为产物：
  描述：

  (-)-5β-methylcodeine 在 potassium tert-butylate 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.03h， 生成 (-)-5β-methyl-6-demethoxythebaine
  参考文献：
  名称：

  Woudenberg, R. H.; Piet, D. P.; Sinnema, A., Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 10, p. 405 - 413

  摘要：

  DOI：

文献信息

• 1-substituted apomorphines as potent dopamine agonists
  作者：Reet Reinart-Okugbeni、Argo Vonk、Ain Uustare、Zsuzsanna Gyulai、Attila Sipos、Ago Rinken

  DOI：10.1016/j.bmc.2013.05.014

  日期：2013.7

  A novel set of 1-substituted apomorphines as dopaminergic agonists were synthesized according to our new strategy employing the acid-catalyzed rearrangement of diversely functionalized 5 beta-substituted-6-demethoxythebaines. The activities of new compounds for dopamine receptors subtypes were evaluated using HEK293 based stable cell lines expressing D-1, D-2L or D-3 receptor subtypes. All studied compounds had affinities in nanomolar range for D-2L and D-3 receptors and the change of the nature of substituent in position 1 had only moderate effect. D-1 receptors were sensitive to the introduction of the 4-OH-benzyl function resulting in an increased affinity. The small hydrophilic group (hydroxymethyl) highly reduced the agonist affinity and potency thereby increasing subtype selectivity. This strategy for selective modulation of affinities and potencies of 1-substituted apomorphines gives essential hints for future design of subtype selective dopaminergic ligands. (C) 2013 Elsevier Ltd. All rights reserved.
• Woudenberg, R. H.; Piet, D. P.; Sinnema, A., Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 10, p. 405 - 413
  作者：Woudenberg, R. H.、Piet, D. P.、Sinnema, A.、Lie, T. S.、Maat, L.

  DOI：——

  日期：——