benzotriazol-1-yl (3β)3,23-dihydroxyolean-12-en-28-oate

• 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: benzotriazol-1-yl (3β)3,23-dihydroxyolean-12-en-28-oate
• 英文别名: benzotriazol-1-yl (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• 化学式: C₃₆H₅₁N₃O₄
• 分子量: 589.819
• InChiKey: RDUJMECAXSRXGG-MZROMGLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  43
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  常春藤皂苷元 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到benzotriazol-1-yl (3β)3,23-dihydroxyolean-12-en-28-oate
  参考文献：
  名称：

  Hederagenin as a triterpene template for the development of new antitumor compounds

  摘要：

  In this study, a series of novel C-28 esters and amides derivatives of hederagenin (He) were designed and synthesized in attempt to develop potent antitumor agents. Their structures were confirmed by MS, IR, H-1 NMR and C-13 NMR spectroscopic analyses and their cytotoxic activities were screened in SRB assays using a panel of six human cancer cell lines. Although most of the compounds displayed moderate to high levels of cytotoxic activity they were all more potent than the natural product He. The most active compounds had either an ethylpyrimidinyl (27) or an ethylpyrrolidinyl (28) substituent, with EC50 in the range of 1.1-6.5 mu M for six human cancer cell lines. Notably, this corresponds to an approximately 30-fold times greater potency than He. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.006

文献信息

• Hederagenin as a triterpene template for the development of new antitumor compounds
  作者：Diego Rodríguez-Hernández、Antonio J. Demuner、Luiz C.A. Barbosa、René Csuk、Lucie Heller

  DOI：10.1016/j.ejmech.2015.10.006

  日期：2015.11

  In this study, a series of novel C-28 esters and amides derivatives of hederagenin (He) were designed and synthesized in attempt to develop potent antitumor agents. Their structures were confirmed by MS, IR, H-1 NMR and C-13 NMR spectroscopic analyses and their cytotoxic activities were screened in SRB assays using a panel of six human cancer cell lines. Although most of the compounds displayed moderate to high levels of cytotoxic activity they were all more potent than the natural product He. The most active compounds had either an ethylpyrimidinyl (27) or an ethylpyrrolidinyl (28) substituent, with EC50 in the range of 1.1-6.5 mu M for six human cancer cell lines. Notably, this corresponds to an approximately 30-fold times greater potency than He. (C) 2015 Elsevier Masson SAS. All rights reserved.