(1R,4aS,10aR)-N-[[(2-chlorophenyl)-diethoxyphosphorylmethyl]carbamothioyl]-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxamide | 1454615-06-5

• 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,4aS,10aR)-N-[[(2-chlorophenyl)-diethoxyphosphorylmethyl]carbamothioyl]-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxamide
• CAS: 1454615-06-5
• 化学式: C₃₂H₄₄ClN₂O₄PS
• 分子量: 619.205
• InChiKey: ZFIJPXMIFTXHJK-VGVWILAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dehydroabietic acid chloride 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 (1R,4aS,10aR)-N-[[(2-chlorophenyl)-diethoxyphosphorylmethyl]carbamothioyl]-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxamide
  参考文献：
  名称：

  Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives

  摘要：

  A series of novel alpha-aminophosphonate derivatives containing DHA structure were designed and synthesized as antitumor agents. In vitro antitumor activities of these compounds against the NCI-H460 (human lung cancer cell), A549 (human lung adenocarcinoma cell), HepG2 (human liver cancer cell) and SKOV3 (human ovarian cancer cell) human cancer cell lines were evaluated and compared with commercial anticancer drug 5-fluorouracil (5-FU), employing standard MTT assay. The pharmacological screening results revealed that many compounds exhibited moderate to high levels of antitumor activities against the tested cancer cell lines and that most demonstrated more potent inhibitory activities compared with the commercial anticancer drug 5-FU. The action mechanism of representative compound 7c was preliminarily investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which indicated that the compound can induce cell apoptosis in NCI-H460 cells. Cell cycle analysis showed that compound 7c mainly arrested NCI-H460 cells in G1 stage. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.005

文献信息

• Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives
  作者：Xiao-Chao Huang、Meng Wang、Ying-Ming Pan、Xiao-Yan Tian、Heng-Shan Wang、Ye Zhang

  DOI：10.1016/j.bmcl.2013.08.005

  日期：2013.10

  A series of novel alpha-aminophosphonate derivatives containing DHA structure were designed and synthesized as antitumor agents. In vitro antitumor activities of these compounds against the NCI-H460 (human lung cancer cell), A549 (human lung adenocarcinoma cell), HepG2 (human liver cancer cell) and SKOV3 (human ovarian cancer cell) human cancer cell lines were evaluated and compared with commercial anticancer drug 5-fluorouracil (5-FU), employing standard MTT assay. The pharmacological screening results revealed that many compounds exhibited moderate to high levels of antitumor activities against the tested cancer cell lines and that most demonstrated more potent inhibitory activities compared with the commercial anticancer drug 5-FU. The action mechanism of representative compound 7c was preliminarily investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which indicated that the compound can induce cell apoptosis in NCI-H460 cells. Cell cycle analysis showed that compound 7c mainly arrested NCI-H460 cells in G1 stage. (C) 2013 Elsevier Ltd. All rights reserved.