1-O-p-nitrobenzoyllycorine | 1384956-45-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 1-O-p-nitrobenzoyllycorine
• 英文别名: [(1S,17S,18S,19S)-17-hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl] 4-nitrobenzoate
• CAS: 1384956-45-9
• 化学式: C₂₃H₂₀N₂O₇
• 分子量: 436.421
• InChiKey: MALJMCIIEURZLS-GUGJDKNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 石蒜碱 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 96.0h， 以17%的产率得到1-O-p-nitrobenzoyllycorine
  参考文献：
  名称：

  Lycorine Derivatives Against Trichomonas vaginalis

  摘要：

  Six lycorine derivatives were prepared, characterized, and evaluated for their in vitro anti‐Trichomonas vaginalis activity. Compounds bearing an acetyl (2), lauroyl (3), benzoyl (4 and 5), and p‐nitrobenzoyl (6 and 7) groups were synthesized. The best activity was achieved with lycorine esterified at C‐2 position with lauroyl group. Preliminary structure–activity relationship points that unprotected OH group at C‐1 and C‐2 is not necessary to the antiparasitic activity, and none of the derivative was less active than lycorine. The lycorine structural requisites required to kill this amitochondriate cell seem to be different in comparison with the derivatives most active against other parasites and tumor cell lines, both mitochondriated cells. This result is an important contribution with our ongoing studies regarding the mechanism of action of the Amaryllidaceae alkaloids on T. vaginalis cell death opening a new perspective to optimize this innovative pharmacological potential.

  DOI：

  10.1111/j.1747-0285.2012.01333.x