methyl (28S)-3-[3β-acetoxy-28-hydroxy-lup-20(29)-en-28-yl]-propiolate | 1228273-19-5

• 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: methyl (28S)-3-[3β-acetoxy-28-hydroxy-lup-20(29)-en-28-yl]-propiolate
• 英文别名: methyl (4S)-4-[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-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-3a-yl]-4-hydroxybut-2-ynoate
• CAS: 1228273-19-5
• 化学式: C₃₆H₅₄O₅
• 分子量: 566.822
• InChiKey: MXPYVKALUXWVPU-KBUIEBNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (28S)-3-[3β-acetoxy-28-hydroxy-lup-20(29)-en-28-yl]-propiolate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以43%的产率得到28-(4-(methylcarboxy)-1H-1,2,3-triazol-5-yl)-3,28-dioxo-28-ethinyllup-20(29)-ene
  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
• 作为产物：
  描述：

  3-O-acetylbetulinal 、 丙炔酸甲酯 在 lithium diisopropyl amide 、 水 、 sodium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以73%的产率得到methyl (28S)-3-[3β-acetoxy-28-hydroxy-lup-20(29)-en-28-yl]-propiolate
  参考文献：
  名称：

  抗肿瘤活性的γ-丁内酯取代的桦木素衍生物的合成及生物学评价

  摘要：

  植物三萜类桦木和桦木酸（BA）是具有有趣药理特性的三萜类。从取代的桦木醛开始，我们将它们用作合成几种γ-丁内酯和丁烯化物的前导结构。使用SRB测定法检测了它们对15种癌细胞系的抗肿瘤活性，并通过台盼蓝试验和DNA阶梯检测证明了它们的凋亡作用。几种化合物显示出比桦木酸更高的活性。

  DOI：

  10.1016/j.bmc.2010.02.042

文献信息

• Synthesis and biological evaluation of antitumor-active γ-butyrolactone substituted betulin derivatives
  作者：René Csuk、Alexander Barthel、Stefan Schwarz、Harish Kommera、Reinhard Paschke

  DOI：10.1016/j.bmc.2010.02.042

  日期：2010.4

  The plant triterpenes betulin and betulinic acid (BA) are triterpenes featuring interesting pharmacological properties. Starting from substituted betulinic aldehydes, we used them as lead structures for the synthesis of several γ-butyrolactones and butenolides. Their antitumor activity was examined for 15 cancer cell lines using a SRB-assay and their apoptotic action was documented by trypan-blue test

  植物三萜类桦木和桦木酸（BA）是具有有趣药理特性的三萜类。从取代的桦木醛开始，我们将它们用作合成几种γ-丁内酯和丁烯化物的前导结构。使用SRB测定法检测了它们对15种癌细胞系的抗肿瘤活性，并通过台盼蓝试验和DNA阶梯检测证明了它们的凋亡作用。几种化合物显示出比桦木酸更高的活性。
• 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.