1-acetyl-2-TBS-lycorine | 1174500-17-4

• 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-acetyl-2-TBS-lycorine
• 英文别名: 1-O-acetyl-2-O-tert-butyldimethylsilyllycorine；1-O-acetyl-2-tert-butyldimethylsilyloxylycorine；1-acetoxy-2-TBS-lycorine；1-Acetoxy-2-tert-butyldimethylsilyl-oxylycorine；[(1S,17S,18S,19S)-17-[tert-butyl(dimethyl)silyl]oxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9,15-tetraen-18-yl] acetate
• CAS: 1174500-17-4
• 化学式: C₂₄H₃₃NO₅Si
• 分子量: 443.615
• InChiKey: IQOBLYMQXROOIM-MYDTUXCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-acetyl-2-TBS-lycorine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到1-O-acetyllycorine
  参考文献：
  名称：

  Selective cytochrome P450 3A4 inhibitory activity of Amaryllidaceae alkaloids

  摘要：

  A library of natural and semi-synthetic Amaryllidaceae alkaloids was screened for cytochrome P450 3A4 (CYP3A4) inhibitory activity. Of the crinane, lycorane and galanthamine representatives examined two semi-synthetic silylated lycorane analogues, accessed via a chemoselective silylation strategy from lycorine, and the natural compound narciclasine exhibited low micromolar activities. Important pharmacological features uncovered include the lack of CYP3A4 inhibitory activity seen for galanthamine and the selective activity that is seen with narciclasine over pancratistatin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.086
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 吡啶 、 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1-acetyl-2-TBS-lycorine
  参考文献：
  名称：

  石蒜碱类化合物在制备抗肿瘤药物的应用

  摘要：

  本发明涉及石蒜碱类化合物(A)在抗肿瘤药物方面的应用，还涉及其各种光学异构体，药学上可接受的盐，溶剂合物以及前药在制备抗肿瘤药物的应用。本发明还涉及含有式(A)结构石蒜碱类化合物的药物组合物在制备抗肿瘤药物的应用。

  公开号：

  CN103304573B

文献信息

• Structure-activity studies on the lycorine pharmacophore: A potent inducer of apoptosis in human leukemia cells
  作者：James McNulty、Jerald J. Nair、Jaume Bastida、Siyaram Pandey、Carly Griffin

  DOI：10.1016/j.phytochem.2009.04.012

  日期：2009.5

  The direct chemoselective differential functionalization of the ring-C hydroxyl groups present in the Amaryllidaceae alkaloid lycorine is described allowing for selective manipulation of the 1,2-hydroxyl groups. A mini-library comprised of synthetic and natural lycorane alkaloids was prepared and their apoptosis-inducing activity investigated in human leukemia (Jurkat) cells. Further insights into the nature of this interesting apoptosis-inducing pharmacophore are described, including the requirement of both free hydroxyl groups in ring-C. (C) 2009 Elsevier Ltd. All rights reserved.
• 石蒜碱类化合物在制备抗肿瘤药物的应用
  申请人：南开大学

  公开号：CN103304573B

  公开（公告）日：2016-01-06

  本发明涉及石蒜碱类化合物(A)在抗肿瘤药物方面的应用，还涉及其各种光学异构体，药学上可接受的盐，溶剂合物以及前药在制备抗肿瘤药物的应用。本发明还涉及含有式(A)结构石蒜碱类化合物的药物组合物在制备抗肿瘤药物的应用。
• Selective cytochrome P450 3A4 inhibitory activity of Amaryllidaceae alkaloids
  作者：James McNulty、Jerald J. Nair、Mohini Singh、Denis J. Crankshaw、Alison C. Holloway、Jaume Bastida

  DOI：10.1016/j.bmcl.2009.04.086

  日期：2009.6

  A library of natural and semi-synthetic Amaryllidaceae alkaloids was screened for cytochrome P450 3A4 (CYP3A4) inhibitory activity. Of the crinane, lycorane and galanthamine representatives examined two semi-synthetic silylated lycorane analogues, accessed via a chemoselective silylation strategy from lycorine, and the natural compound narciclasine exhibited low micromolar activities. Important pharmacological features uncovered include the lack of CYP3A4 inhibitory activity seen for galanthamine and the selective activity that is seen with narciclasine over pancratistatin. (C) 2009 Elsevier Ltd. All rights reserved.