(6S,6aR)-1,2-dimethoxy-6-methyl-6-oxo-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline | 104385-30-0

• 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: (6S,6aR)-1,2-dimethoxy-6-methyl-6-oxo-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• 英文别名: nuciferine N-oxide；Nuciferine N-Oxide；(6aR)-1,2-dimethoxy-6-methyl-6-oxido-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium
• CAS: 104385-30-0
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: SAWSWZQULQPSLR-IWPPFLRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  36.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6S,6aR)-1,2-dimethoxy-6-methyl-6-oxo-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 在 sodium tetrahydroborate 、 硫酸 、 锌 作用下， 以 氯仿 、 水 为溶剂， 反应 6.5h， 生成 3,4-二甲氧基-N,N-二甲基-1-菲乙胺
  参考文献：
  名称：

  Lu, Sheng-Teh; Wu, Yang-Chang, Heterocycles, 1985, vol. 23, # 12, p. 3085 - 3094

  摘要：

  DOI：
• 作为产物：
  描述：

  荷叶碱 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以84%的产率得到(6S,6aR)-1,2-dimethoxy-6-methyl-6-oxo-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
  参考文献：
  名称：

  通过[Mn（TDCPP）Cl]催化的N胺化反应，从天然脂肪族叔生物碱（R3N）直接制备未保护的氨基酰亚胺（R3N + -NH-）。

  摘要：

  天然脂肪族叔胺生物碱的面板（R 3 N）直接转化为R 3 Ñ + -NH - （无需制备保护的胺化酰亚胺- [R 3 Ñ + -NR' -接着脱保护）由[Mn（上TDCPP）氯在温和的反应条件下，以O-（2,4-二硝基苯基）羟胺为氮源，经[ - ]催化的N-胺化反应，收率高达98％。

  DOI：

  10.1039/d0cc02934c

文献信息

• Synthesis and structure–activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors
  作者：Zhongduo Yang、Zhuwen Song、Weiwei Xue、Jie Sheng、Zongmei Shu、Yin Shi、Jibei Liang、Xiaojun Yao

  DOI：10.1007/s00044-013-0905-9

  日期：2014.6

  Acetylcholinesterase inhibitors (AChEIs) are currently the best available pharmacotherapy for Alzheimer patients, but because of bioavailability issues, there is still great interest in discovering better AChEIs. The aporphine alkaloid is an important class of natural products, which shows diverse biological activity, such as acetylcholinesterase inhibitory activity. To find new lead AChEIs compounds, eight aporphine alkaloids were synthesized by O-dealkylation, N-dealkylation, and ring aromatization reactions using nuciferine as raw material. The anti-acetylcholinesterase activity of synthesized compounds was measured using modified Ellman's method. The results showed that some synthesized compounds exhibited higher affinity to AChE than the parent compound nuciferine. Among these compounds, 1,2-dihydroxyaporphine (2) and dehydronuciferine (5) were the most active compounds (IC50 = 28 and 25 mu g/mL, respectively). Preliminary analysis of structure-activity relationships suggested that aromatization of the C ring, the presence of the alkoxyl group at C1 and the hydroxy group at C2 position as well as the alkyl substituent at the N atom were favorable to the acetylcholinesterase inhibition. Molecular docking was also applied to predict the binding modes of compounds 1, 2, and 9 into the huperzine A binding site of AChE.
• Direct preparation of unprotected aminimides (R₃N⁺–NH⁻) from natural aliphatic tertiary alkaloids (R₃N) by [Mn(TDCPP)Cl]-catalysed <i>N</i>-amination reaction
  作者：Shilong Zhang、Yungen Liu、Fangrong Xing、Chi-Ming Che

  DOI：10.1039/d0cc02934c

  日期：——

  alkaloids (R3N) were directly converted to R3N+–NH− (without the need to prepare protected aminimides R3N+–NR′− followed by deprotection) by [Mn(TDCPP)Cl]-catalysed N-amination reaction, with O-(2,4-dinitrophenyl)hydroxylamine as the nitrogen source, in up to 98% yields under mild reaction conditions.

  天然脂肪族叔胺生物碱的面板（R 3 N）直接转化为R 3 Ñ + -NH - （无需制备保护的胺化酰亚胺- [R 3 Ñ + -NR' -接着脱保护）由[Mn（上TDCPP）氯在温和的反应条件下，以O-（2,4-二硝基苯基）羟胺为氮源，经[ - ]催化的N-胺化反应，收率高达98％。
• Lu, Sheng-Teh; Wu, Yang-Chang, Heterocycles, 1985, vol. 23, # 12, p. 3085 - 3094
  作者：Lu, Sheng-Teh、Wu, Yang-Chang

  DOI：——

  日期：——