N(4)-methylechitamidine iodide

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 马钱子生物碱
• 英文名称: N(4)-methylechitamidine iodide
• 英文别名: methyl (1R,11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-14-methyl-8-aza-14-azoniapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carboxylate;iodide
• 化学式: C₂₁H₂₇N₂O₃*I
• 分子量: 482.361
• InChiKey: BALSBCGIHBFPIE-KKQBYPBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N(4)-methylechitamidine iodide 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 17-carboxyl-N(4)-methylechitamidine iodide
  参考文献：
  名称：

  Terpenoid Indole Alkaloids from Winchia calophylla

  摘要：

  Three new indole alkaloids, N(4)-demethyl-12-metboxyalstogustine (1), 17-carboxyl-N(4)-methylechitamidine chloride (2), and 17-carboxyl-12-niethoxy-N(4)-methylechitamidine chloride (3), along with 15 known alkaloids, were isolated from the ethanolic extract of the stem bark of Winchia calophylla. The structures of 1-3 were elucidated on the basis of spectroscopic means and chemical methods. The determination of relative configurations at C-19 and C-20 for 1-3 was aided by C-13 NMR spectroscopic data. The absolute configurations of alkaloids 1-3 were determined by direct comparison of their CD spectra with those of known alkaloids. All the alkaloids were tested in cytotoxic assays against P-388 and A-549 tumor cell lines, and only two of them showed weak activity against the A-549 cell line.

  DOI：

  10.1021/np0502701
• 作为产物：
  描述：

  (19S)-2,16-二去氢-19-羟基-枯苒-17-酸甲酯 、 碘甲烷 以 丙酮 为溶剂， 反应 2.0h， 生成 N(4)-methylechitamidine iodide
  参考文献：
  名称：

  Terpenoid Indole Alkaloids from Winchia calophylla

  摘要：

  Three new indole alkaloids, N(4)-demethyl-12-metboxyalstogustine (1), 17-carboxyl-N(4)-methylechitamidine chloride (2), and 17-carboxyl-12-niethoxy-N(4)-methylechitamidine chloride (3), along with 15 known alkaloids, were isolated from the ethanolic extract of the stem bark of Winchia calophylla. The structures of 1-3 were elucidated on the basis of spectroscopic means and chemical methods. The determination of relative configurations at C-19 and C-20 for 1-3 was aided by C-13 NMR spectroscopic data. The absolute configurations of alkaloids 1-3 were determined by direct comparison of their CD spectra with those of known alkaloids. All the alkaloids were tested in cytotoxic assays against P-388 and A-549 tumor cell lines, and only two of them showed weak activity against the A-549 cell line.

  DOI：

  10.1021/np0502701