2-phenylthioapocodeine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 2-phenylthioapocodeine
• 英文别名: (6aR)-10-methoxy-6-methyl-2-phenylsulfanyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol
• 化学式: C₂₄H₂₃NO₂S
• 分子量: 389.518
• InChiKey: FYDAJUNGVQCWJI-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  蒂巴因 、 苯硫酚 在 甲烷磺酸 作用下， 反应 0.5h， 以48%的产率得到2-phenylthioapocodeine
  参考文献：
  名称：

  硫代水杨酸存在下蒂巴因酸催化重排形成新的多环杂化体系

  摘要：

  在苯硫酚存在下，蒂巴因 (1) 的甲磺酸催化重排产生 2-苯基硫代阿扑可待因 (7)，其 O-去甲基化产生 2-苯基硫代阿扑吗啡 (8)。用硫代水杨酸对 1 进行类似的转化，得到醚 (6) 和 (11) 以及多环酮 (12) 和多环缩醛 (15)。在用酸处理缩醛(15)后，制备了噻吨盐(16)。

  DOI：

  10.3987/com-01-9378

文献信息

• Formation of a New Polycyclic Heteroring System by the Acid-catalyzed Rearrangement of Thebaine in the Presence of Thiosalicylic Acid
  作者：Sándor Berényi、Miklós Tóth、Susanna Gyulai、László Szilágyi

  DOI：10.3987/com-01-9378

  日期：——

  The methanesulfonic acid-catalyzed rearrangement of thebaine (1) in the presence of thiophenol resulted in 2-phenylthioapocodeine (7), whose O-demethylation gave 2-phenylthioapomorphine (8). An analogous transformation of1 with thiosalicylic acid furnished the ethers (6) and (11) together with a polycyclic ketone (12) and a polycyclic acetal (15). Upon treatment of the acetal (15) with acid the thioxanthylium

  在苯硫酚存在下，蒂巴因 (1) 的甲磺酸催化重排产生 2-苯基硫代阿扑可待因 (7)，其 O-去甲基化产生 2-苯基硫代阿扑吗啡 (8)。用硫代水杨酸对 1 进行类似的转化，得到醚 (6) 和 (11) 以及多环酮 (12) 和多环缩醛 (15)。在用酸处理缩醛(15)后，制备了噻吨盐(16)。
• New 2-thioether-substituted apomorphines as potent and selective dopamine D2 receptor agonists
  作者：Reet Reinart、Zsuzsanna Gyulai、Sándor Berényi、Sándor Antus、Argo Vonk、Ago Rinken、Attila Sipos

  DOI：10.1016/j.ejmech.2011.04.028

  日期：2011.7

  A set of novel apomorphine derivatives were synthesized with diversely functionalized side chains in the proximity of position 2 of the aporphine skeleton. Amino and/or carboxylic functions were introduced to this region of the backbone to test their pharmacological effects. During the synthesis of 2-(S-3-mercaptopropionic acid)-derivative a heteroring-fused congener was also isolated. The structural elucidation confirmed that the formation of this product was in accordance with our previous observations on the reaction of thebaine (2) with thiosalycilic acid. All the novel apomorphine congeners 4a-g were neuropharmacologically characterized to discover their dopaminergic profiles. Two derivatives were identified as D-2 full agonists equipotent with apomorphine (1) having significantly increased D-2/D-1 selectivity ratios. (C) 2011 Elsevier Masson SAS. All rights reserved.