cycleanorine | 38769-08-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: cycleanorine
• 英文别名: 6,7,12,6'-tetramethoxy-2-methyl-(1βH)-berbamane；N^2'-demethyl-tetrandrine；N^2'-nortetrandrine；Tetrandrine metabolite, N'-nor-D-；(1S,14S)-9,20,21,25-tetramethoxy-15-methyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaene
• CAS: 38769-08-3
• 化学式: C₃₇H₄₀N₂O₆
• 分子量: 608.734
• InChiKey: LHIFPLJVJKKRTD-VMPREFPWSA-N

物化性质

• 沸点：
  720.2±60.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  45
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  70.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cycleanorine 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以8.9%的产率得到2'-N-noratherospermoline
  参考文献：
  名称：

  Studies on Inhibitory Activity against Acetylcholinesterase of New Bisbenzylisoquinoline Alkaloid and Its Related Compounds

  摘要：

  A new phenolic bisbenzylisoquinoline (BBI) alkaloid named 2'-N-norfangchinoline was isolated from the root of Stephania tetrandra S. MOORE along withfangchinoline (2) and atherospermoline (3). The chemical structure of 2'-N-norfangchinoline was proved to be 4 by spectral analyses and chemical methods. Moreover three phenolic BBI alkaloidal compounds, 2,2'-N,N-dinorfangchinoline (8), 2'-N-noratherospermoline (9), 2-N-norfangchinoline (10) were derived from tetrandrine (1). And 12-O-acetyl atherospermoline (11) was obtained by partial acetylation of atherospermoline (3). Seven phenolic BBI compounds (2, 3, 4, 8, 9, 10, and 11) also have the inhibitory effect on acetylcholinesterase.

  DOI：

  10.3987/com-97-7935
• 作为产物：
  描述：

  汉防己甲素 在 丙烷-1-硫醇 、 potassium tert-butylate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 144.0h， 生成 cycleanorine
  参考文献：
  名称：

  Cycla peltata的新生物碱和相关人工制品。

  摘要：

  DOI：

  10.1021/jo00950a016

文献信息

• Tumor Inhibitors. LXXIX. New alkaloids and related artifacts from Cyclea peltata
  作者：S. Morris Kupchan、Adris J. Liepa、Robert L. Baxter、Harold P. J. Hintz

  DOI：10.1021/jo00950a016

  日期：1973.5
• Studies on Inhibitory Activity against Acetylcholinesterase of New Bisbenzylisoquinoline Alkaloid and Its Related Compounds
  作者：Tatsunori Ogino、Takuji Yamaguchi、Toshitsugu Sato、Hiroshi Sasaki、Ko Sugama、Minoru Okada、Masao Maruno

  DOI：10.3987/com-97-7935

  日期：——

  A new phenolic bisbenzylisoquinoline (BBI) alkaloid named 2'-N-norfangchinoline was isolated from the root of Stephania tetrandra S. MOORE along withfangchinoline (2) and atherospermoline (3). The chemical structure of 2'-N-norfangchinoline was proved to be 4 by spectral analyses and chemical methods. Moreover three phenolic BBI alkaloidal compounds, 2,2'-N,N-dinorfangchinoline (8), 2'-N-noratherospermoline (9), 2-N-norfangchinoline (10) were derived from tetrandrine (1). And 12-O-acetyl atherospermoline (11) was obtained by partial acetylation of atherospermoline (3). Seven phenolic BBI compounds (2, 3, 4, 8, 9, 10, and 11) also have the inhibitory effect on acetylcholinesterase.