ethyl 1-butoxy-2-methoxy-4,5,6a,7-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline-6-carboxylate | 1160872-94-5

• 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: ethyl 1-butoxy-2-methoxy-4,5,6a,7-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline-6-carboxylate
• CAS: 1160872-94-5
• 化学式: C₂₅H₂₉NO₆
• 分子量: 439.508
• InChiKey: QLGSCWVSELYKIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-butoxy-2-methoxy-4,5,6a,7-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline-6-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以91%的产率得到1-butoxy-2-methoxy-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline
  参考文献：
  名称：

  (±)-Nantenine analogs as antagonists at human 5-HT2A receptors: C1 and flexible congeners

  摘要：

  C1 and flexible analogs of (+/-)-nantenine were synthesized and evaluated for antagonist activity at human 5-HT(2)A receptors in a calcium mobilization assay. This work has resulted in the identification of the most potent 5-HT2A antagonist known based on an aporphine. Our results also suggest that the C1 position may be a key site for increasing 5-HT2A antagonist activity in this compound series. In addition, the structural rigidity of the aporphine core appears to be required for nantenine to function as a 5-HT2A antagonist. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.048
• 作为产物：
  描述：

  正溴丁烷 、 1-Hydroxy-2-methoxy-4,5,6a,7-tetrahydro-9,11-dioxa-6-aza-benzo[fg]cyclopenta[b]anthracene-6-carboxylic acid ethyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 ethyl 1-butoxy-2-methoxy-4,5,6a,7-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline-6-carboxylate
  参考文献：
  名称：

  (±)-Nantenine analogs as antagonists at human 5-HT2A receptors: C1 and flexible congeners

  摘要：

  C1 and flexible analogs of (+/-)-nantenine were synthesized and evaluated for antagonist activity at human 5-HT(2)A receptors in a calcium mobilization assay. This work has resulted in the identification of the most potent 5-HT2A antagonist known based on an aporphine. Our results also suggest that the C1 position may be a key site for increasing 5-HT2A antagonist activity in this compound series. In addition, the structural rigidity of the aporphine core appears to be required for nantenine to function as a 5-HT2A antagonist. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.048