6-acetyl-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol | 58793-64-9

• 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: 6-acetyl-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
• 英文别名: 1-(2,9-dihydroxy-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-yl)ethanone
• CAS: 58793-64-9
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: QSHGKOORSATGIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-acetyl-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 8-(2-(Isopropylamino)ethyl)-3,5-dimethoxyphenanthrene-2,6-diol
  参考文献：
  名称：

  Litebamine N-Homologues:  Preparation and Anti-Acetylcholinesterase Activity

  摘要：

  Litebamine N-homologues were easily prepared from laurolitsine, generally via three reaction steps (N-alkylation, solvolysis with 1 M NH4OAc under reflux, and the Mannich reaction) in more than 80% overall yield. Among the prepared compounds, N-propyl-, N-isobutyl-, and N-isopropylnorlitebamines exhibited moderate antiacetylcholinesterase activity (IC50 Ca 7.0 mu M), while the corresponding N-metho salt of N-propylnorlitebamine showed potent activity (IC50 2.70 mu M).

  DOI：

  10.1021/np970298f
• 作为产物：
  描述：

  laurolitsine 、 乙酸酐 以 N,N-二甲基甲酰胺 为溶剂， 以3.60 g的产率得到6-acetyl-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
  参考文献：
  名称：

  Litebamine N-Homologues:  Preparation and Anti-Acetylcholinesterase Activity

  摘要：

  Litebamine N-homologues were easily prepared from laurolitsine, generally via three reaction steps (N-alkylation, solvolysis with 1 M NH4OAc under reflux, and the Mannich reaction) in more than 80% overall yield. Among the prepared compounds, N-propyl-, N-isobutyl-, and N-isopropylnorlitebamines exhibited moderate antiacetylcholinesterase activity (IC50 Ca 7.0 mu M), while the corresponding N-metho salt of N-propylnorlitebamine showed potent activity (IC50 2.70 mu M).

  DOI：

  10.1021/np970298f

文献信息

• 2a-Alkylnorlitebamines and (7a,8)-didehydroisohomoaporphines: Synthesis and antiacetylcholinesterase activity verified via <i>in silico</i> molecular docking
  作者：Ya-En Cheng、Sheau-Ling Ho、Sheng-Fa Tsai、Ming-Che Cheng、Ching-Yi Lu、Chia-Chuan Chang、Shoei-Sheng Lee

  DOI：10.1080/00397911.2023.2274365

  日期：2023.12.17
• Litebamine <i>N</i>-Homologues:  Preparation and Anti-Acetylcholinesterase Activity
  作者：Chi-Ming Chiou、Jaw-Jou Kang、Shoei-Sheng Lee

  DOI：10.1021/np970298f

  日期：1998.1.1

  Litebamine N-homologues were easily prepared from laurolitsine, generally via three reaction steps (N-alkylation, solvolysis with 1 M NH4OAc under reflux, and the Mannich reaction) in more than 80% overall yield. Among the prepared compounds, N-propyl-, N-isobutyl-, and N-isopropylnorlitebamines exhibited moderate antiacetylcholinesterase activity (IC50 Ca 7.0 mu M), while the corresponding N-metho salt of N-propylnorlitebamine showed potent activity (IC50 2.70 mu M).