(3S,28S)-3-O-acetyl-28-[3-thiomorpholin-4-yl-prop-1-yn-1-yl]lup-20(29)-en-3,28-diol hydrochloride | 1417539-23-1

• 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: (3S,28S)-3-O-acetyl-28-[3-thiomorpholin-4-yl-prop-1-yn-1-yl]lup-20(29)-en-3,28-diol hydrochloride
• 英文别名: [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-[(1S)-1-hydroxy-4-thiomorpholin-4-ylbut-2-ynyl]-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;hydrochloride
• CAS: 1417539-23-1
• 化学式: C₃₉H₆₁NO₃S*ClH
• 分子量: 660.445
• InChiKey: AQWQVCKCHDNRFZ-ANJXUMOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  75.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-O-acetylbetulinal 在 copper(l) iodide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 34.0h， 生成 (3S,28S)-3-O-acetyl-28-[3-thiomorpholin-4-yl-prop-1-yn-1-yl]lup-20(29)-en-3,28-diol hydrochloride
  参考文献：
  名称：

  Cytotoxic betulin-derived hydroxypropargylamines trigger apoptosis

  摘要：

  Several novel betulin derivatives were prepared and evaluated for their antitumor activity. Among others, 3-O-acetylbetulinic aldehyde served as an ideal starting material for the synthesis of 28-acetylenic derivatives that were further transformed into Mannich bases. These hydroxypropargylamines were screened for their antitumor activity in a panel of nine human cancer cell lines in a sulforhodamine B (SRB) assay. Several compounds showed a noteworthy antitumor activity. The results from acridine orange/propidium iodide staining and annexinV-FITC assays as well as DNA laddering experiments provided evidence for an apoptotic cell death. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.016

文献信息

• Cytotoxic betulin-derived hydroxypropargylamines trigger apoptosis
  作者：René Csuk、Ronny Sczepek、Bianka Siewert、Christoph Nitsche

  DOI：10.1016/j.bmc.2012.11.016

  日期：2013.1

  Several novel betulin derivatives were prepared and evaluated for their antitumor activity. Among others, 3-O-acetylbetulinic aldehyde served as an ideal starting material for the synthesis of 28-acetylenic derivatives that were further transformed into Mannich bases. These hydroxypropargylamines were screened for their antitumor activity in a panel of nine human cancer cell lines in a sulforhodamine B (SRB) assay. Several compounds showed a noteworthy antitumor activity. The results from acridine orange/propidium iodide staining and annexinV-FITC assays as well as DNA laddering experiments provided evidence for an apoptotic cell death. (C) 2012 Elsevier Ltd. All rights reserved.