2-[4-(2-chlorobenzoyl)piperazin-1-yl]ethyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate | 1400745-17-6

• 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-[4-(2-chlorobenzoyl)piperazin-1-yl]ethyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• CAS: 1400745-17-6
• 化学式: C₄₃H₆₃ClN₂O₄
• 分子量: 707.437
• InChiKey: AUTAGLMNODBNTI-QTUQHGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  50
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  熊果酸 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.67h， 生成 2-[4-(2-chlorobenzoyl)piperazin-1-yl]ethyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel ursolic acid derivatives containing an acyl piperazine moiety

  摘要：

  This study designed and synthesized a series of novel ursolic acid derivatives in an attempt to develop potent antitumor agents. Their structures were confirmed using MS. IR, H-1 NMR and C-13 NMR. The inhibitory activities of the title compounds against the MGC-803 (gastric cancer cell) and Bcap-37 (breast cancer cell) human cancer cell lines were evaluated using standard MIT assay in vitro. The pharmacological results showed that some of the compounds displayed moderate to high levels of antitumor activities against the tested cancer cell lines and that most exhibited more potent inhibitory activities compared with ursolic acid. The mechanism of compound 4b was preliminarily investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, TUNEL assay and flow cytometry, which revealed that the compound can induce cell apoptosis in MGC-803 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.048

文献信息

• Synthesis and cytotoxicity of novel ursolic acid derivatives containing an acyl piperazine moiety
  作者：Ming-Chuan Liu、Sheng-Jie Yang、Lin-Hong Jin、De-Yu Hu、Wei Xue、Bao-An Song、Song Yang

  DOI：10.1016/j.ejmech.2012.08.048

  日期：2012.12

  This study designed and synthesized a series of novel ursolic acid derivatives in an attempt to develop potent antitumor agents. Their structures were confirmed using MS. IR, H-1 NMR and C-13 NMR. The inhibitory activities of the title compounds against the MGC-803 (gastric cancer cell) and Bcap-37 (breast cancer cell) human cancer cell lines were evaluated using standard MIT assay in vitro. The pharmacological results showed that some of the compounds displayed moderate to high levels of antitumor activities against the tested cancer cell lines and that most exhibited more potent inhibitory activities compared with ursolic acid. The mechanism of compound 4b was preliminarily investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, TUNEL assay and flow cytometry, which revealed that the compound can induce cell apoptosis in MGC-803 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.