N-[3β-hydroxy-urs-12-en-28-oyl]-amino-N-(3,4-dimethylphenyl) piperazine-1-carbothioamide

• 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: N-[3β-hydroxy-urs-12-en-28-oyl]-amino-N-(3,4-dimethylphenyl) piperazine-1-carbothioamide
• 英文别名: 4-[(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-carbonyl]-N-(3,4-dimethylphenyl)piperazine-1-carbothioamide
• 化学式: C₄₃H₆₅N₃O₂S
• 分子量: 688.074
• InChiKey: PICFSEHVYMNKFC-KYBOVCFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  49
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  87.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  熊果酸 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 47.0h， 生成 N-[3β-hydroxy-urs-12-en-28-oyl]-amino-N-(3,4-dimethylphenyl) piperazine-1-carbothioamide
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of novel ursolic acid derivatives as potential anticancer agents

  摘要：

  A series of novel ursolic acid (UA) derivatives modified at the C-3 and the C-28 positions were designed and synthesized in an attempt to develop potential antitumor agents. The in vitro cytotoxicity were evaluated against five cancer cell lines (MGC-803, HCT-116, T24, HepG2 and A549 cell lines) and a normal cell (HL-7702) by MTT assay. The screening results indicated that some of these target compounds displayed moderate to high levels of antiproliferative activities compared with ursolic acid and 5-fluorouracil (5-FU), and exhibited much lower cytotoxicity than 5-FU, indicating that the targeted compounds had selective and significant effect on the cell lines. The induction of apoptosis and affects on the cell cycle distribution of compound 6r were investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which revealed that the antitumor activity of 6r was possibly achieved through the induction of cell apoptosis by G1 cell-cycle arrest. Western blot and qRT-PCR (quantitative real-time PCR) experiments demonstrated that compound 6r may induce apoptosis through both of intrinsic and extrinsic apoptosis pathway. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.051

文献信息

• Design, synthesis and in vitro evaluation of novel ursolic acid derivatives as potential anticancer agents
  作者：Shi-Xian Hua、Ri-Zhen Huang、Man-Yi Ye、Ying-Ming Pan、Gui-Yang Yao、Ye Zhang、Heng-Shan Wang

  DOI：10.1016/j.ejmech.2015.03.051

  日期：2015.5

  A series of novel ursolic acid (UA) derivatives modified at the C-3 and the C-28 positions were designed and synthesized in an attempt to develop potential antitumor agents. The in vitro cytotoxicity were evaluated against five cancer cell lines (MGC-803, HCT-116, T24, HepG2 and A549 cell lines) and a normal cell (HL-7702) by MTT assay. The screening results indicated that some of these target compounds displayed moderate to high levels of antiproliferative activities compared with ursolic acid and 5-fluorouracil (5-FU), and exhibited much lower cytotoxicity than 5-FU, indicating that the targeted compounds had selective and significant effect on the cell lines. The induction of apoptosis and affects on the cell cycle distribution of compound 6r were investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which revealed that the antitumor activity of 6r was possibly achieved through the induction of cell apoptosis by G1 cell-cycle arrest. Western blot and qRT-PCR (quantitative real-time PCR) experiments demonstrated that compound 6r may induce apoptosis through both of intrinsic and extrinsic apoptosis pathway. (C) 2015 Elsevier Masson SAS. All rights reserved.