2-[2-[(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-9-(1,3-benzodioxol-5-ylmethylamino)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]prop-2-enylamino]ethanol | 1253079-96-7

• 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: 2-[2-[(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-9-(1,3-benzodioxol-5-ylmethylamino)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]prop-2-enylamino]ethanol
• CAS: 1253079-96-7
• 化学式: C₄₀H₆₂N₂O₄
• 分子量: 634.943
• InChiKey: JFJDNAMZIYNXPC-CNHRZFDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧基苄胺 、 (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-1-[3-(2-hydroxyethylamino)prop-1-en-2-yl]-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one 在 sodium cyanoborohydride 作用下， 生成 2-[2-[(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-9-(1,3-benzodioxol-5-ylmethylamino)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]prop-2-enylamino]ethanol
  参考文献：
  名称：

  Synthesis, proapoptotic screening, and structure–activity relationships of novel aza-lupane triterpenoids

  摘要：

  Apoptosis is a highly regulated process by which excessive cells are eliminated in order to maintain normal cell development and tissue homeostasis. Resistance to apoptosis often contributes to failure in cancer prevention and treatment. Apoptotic cell death regulators are considered important targets for discovery and development of new therapeutic agents in oncology research. A class of novel aza-lupane triterpenoids were designed, synthesized, and evaluated for antitumor activity against a panel of cancer cell lines of different histogenic origin and for ability to induce apoptosis. 3,30-Bis(aza) derivatives were identified not only to possess improved cytotoxicity compared to the natural product betulinic acid but also to affect cell death predominantly via apoptosis, whereas the mono(aza) derivatives apparently triggered cell death via different, non-apoptotic pathway(s). (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.120

文献信息

• Synthesis, proapoptotic screening, and structure–activity relationships of novel aza-lupane triterpenoids
  作者：Aye Aye Mar、Erika L. Szotek、Ali Koohang、William P. Flavin、David A. Eiznhamer、Michael T. Flavin、Ze-Qi Xu

  DOI：10.1016/j.bmcl.2010.07.120

  日期：2010.9

  Apoptosis is a highly regulated process by which excessive cells are eliminated in order to maintain normal cell development and tissue homeostasis. Resistance to apoptosis often contributes to failure in cancer prevention and treatment. Apoptotic cell death regulators are considered important targets for discovery and development of new therapeutic agents in oncology research. A class of novel aza-lupane triterpenoids were designed, synthesized, and evaluated for antitumor activity against a panel of cancer cell lines of different histogenic origin and for ability to induce apoptosis. 3,30-Bis(aza) derivatives were identified not only to possess improved cytotoxicity compared to the natural product betulinic acid but also to affect cell death predominantly via apoptosis, whereas the mono(aza) derivatives apparently triggered cell death via different, non-apoptotic pathway(s). (c) 2010 Elsevier Ltd. All rights reserved.