((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(((tert-butoxycarbonyl)glycyl)oxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysen-3a-yl)methyl (tert-butoxycarbonyl)glycinate | 1187976-89-1

• 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: ((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(((tert-butoxycarbonyl)glycyl)oxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysen-3a-yl)methyl (tert-butoxycarbonyl)glycinate
• CAS: 1187976-89-1
• 化学式: C₄₄H₇₂N₂O₈
• 分子量: 757.064
• InChiKey: PNIYOYOODWAIOY-DRWNXRBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.15
• 重原子数：
  54.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(((tert-butoxycarbonyl)glycyl)oxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysen-3a-yl)methyl (tert-butoxycarbonyl)glycinate 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以81%的产率得到
  参考文献：
  名称：

  Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells

  摘要：

  Betulin and betulinic acid are naturally occurring pentacyclic triterpenes showing cytotoxicity towards a number of cancer cell lines. Unfortunately they are practically insoluble in aqueous media and therefore their overall absorption index is not satisfactory. We have modified structures of both compounds by simple transformation to mono-and disubstituted esters of L-amino acids. This allowed us to achieve better water solubility without loss of the observed earlier anticancer properties. Comet assay on various cancer cell lines demonstrate that these compounds act via an apoptotic mechanism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.046
• 作为产物：
  描述：

  BOC-甘氨酸 、 白桦脂醇 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 以91%的产率得到((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(((tert-butoxycarbonyl)glycyl)oxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysen-3a-yl)methyl (tert-butoxycarbonyl)glycinate
  参考文献：
  名称：

  Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells

  摘要：

  Betulin and betulinic acid are naturally occurring pentacyclic triterpenes showing cytotoxicity towards a number of cancer cell lines. Unfortunately they are practically insoluble in aqueous media and therefore their overall absorption index is not satisfactory. We have modified structures of both compounds by simple transformation to mono-and disubstituted esters of L-amino acids. This allowed us to achieve better water solubility without loss of the observed earlier anticancer properties. Comet assay on various cancer cell lines demonstrate that these compounds act via an apoptotic mechanism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.046