3-[[(6aR)-11-hydroxy-10-methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-yl]sulfanyl]propanoic acid | 1312883-60-5

• 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: 3-[[(6aR)-11-hydroxy-10-methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-yl]sulfanyl]propanoic acid
• CAS: 1312883-60-5
• 化学式: C₂₁H₂₃NO₄S
• 分子量: 385.484
• InChiKey: KGLCKDVVMWFJLK-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  蒂巴因 、 3-巯基丙酸 在 甲烷磺酸 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 、 3-[[(6aR)-11-hydroxy-10-methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-yl]sulfanyl]propanoic acid
  参考文献：
  名称：

  New 2-thioether-substituted apomorphines as potent and selective dopamine D2 receptor agonists

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.04.028

文献信息

• 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.