(4R)-3-(dimethylamino)-4-[3β-hydroxy-28-norlup-20(29)-en-17β-yl]-2-butenolide | 1256362-69-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4R)-3-(dimethylamino)-4-[3β-hydroxy-28-norlup-20(29)-en-17β-yl]-2-butenolide
• 英文别名: [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-[(2S)-3-(dimethylamino)-5-oxo-2H-furan-2-yl]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
• CAS: 1256362-69-2
• 化学式: C₃₇H₅₇NO₄
• 分子量: 579.864
• InChiKey: XOVCGGPDHNMQPI-UKLVWQCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (28S)-3-[3β-acetoxy-28-hydroxy-lup-20(29)-en-28-yl]-propiolate 、 二甲基铵-二甲基 以 乙醇 为溶剂， 反应 12.0h， 以68%的产率得到(4R)-3-(dimethylamino)-4-[3β-hydroxy-28-norlup-20(29)-en-17β-yl]-2-butenolide
  参考文献：
  名称：

  Synthesis, cytotoxicity and liposome preparation of 28-acetylenic betulin derivatives

  摘要：

  Several novel betulin derivatives were prepared and evaluated for their antitumor activity. 3-O-Acetyl-betulinic aldehyde served as an ideal starting material for the synthesis of 28-acetylenic derivatives. These compounds were further transformed into pyrazoles and 1,2,3-triazoles. Also, the synthesis of 3-amino substituted butenolides was carried out. The compounds were screened for their antitumor activity in a panel of 15 human cancer cell lines in a sulforhodamine B (SRB) assay. Several compounds showed a noteworthy antitumor activity. In addition, the possibility of encapsulation into liposomes was examined, thereby resulting in an increased cytotoxicity. The results from a trypan-blue test and from DNA laddering provided evidence for an apoptotic cell death. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.023

文献信息

• Synthesis, cytotoxicity and liposome preparation of 28-acetylenic betulin derivatives
  作者：René Csuk、Alexander Barthel、Ralph Kluge、Dieter Ströhl

  DOI：10.1016/j.bmc.2010.08.023

  日期：2010.10.15

  Several novel betulin derivatives were prepared and evaluated for their antitumor activity. 3-O-Acetyl-betulinic aldehyde served as an ideal starting material for the synthesis of 28-acetylenic derivatives. These compounds were further transformed into pyrazoles and 1,2,3-triazoles. Also, the synthesis of 3-amino substituted butenolides was carried out. The compounds were screened for their antitumor activity in a panel of 15 human cancer cell lines in a sulforhodamine B (SRB) assay. Several compounds showed a noteworthy antitumor activity. In addition, the possibility of encapsulation into liposomes was examined, thereby resulting in an increased cytotoxicity. The results from a trypan-blue test and from DNA laddering provided evidence for an apoptotic cell death. (C) 2010 Elsevier Ltd. All rights reserved.