(S)-2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(naphthalen-2-yl)propanamido)-3-phenylpropyl benzoate | 1228823-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(naphthalen-2-yl)propanamido)-3-phenylpropyl benzoate
• 英文别名: [(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-naphthalen-2-ylpropanoyl]amino]-3-phenylpropyl] benzoate
• CAS: 1228823-13-9
• 化学式: C₄₄H₃₈N₂O₅
• 分子量: 674.796
• InChiKey: BOFAFUDNNLNAMY-HXOSKORISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl (S)-1-((S)-1-hydroxy-3-phenylpropan-2-ylamino)-3-(naphthalen-2-yl)-1-oxopropan-2-ylcarbamate 、 苯甲酸酐 在 吡啶 作用下， 反应 6.0h， 以66%的产率得到(S)-2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(naphthalen-2-yl)propanamido)-3-phenylpropyl benzoate
  参考文献：
  名称：

  Cytotoxic N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides: Structure–activity relationships and synergistic studies

  摘要：

  The synthesis and cytotoxic evaluation of a series of Fmoc-based dipeptides are described. Among the thirty compounds, 4a, 8a, 12a, 2b, 4b, 10b, 3c, 4c and 6c showed potent activity against HepG2, Hep3B, MCF-7, MDA-MB-231, A549 and Ca9-22 human cancer cell lines. The most active compounds (10a and 10c) showed relatively good sensitivity toward HepG2 and Ca9-22 cell lines with IC(50) values of 1 0 and 0 4 mu M, respectively. Additionally, compound 10c was threefold more potent than doxorubicin, the positive control, against the Ca9-22 cell line. Furthermore, 10c showed a synergistic effect and increased the cytotoxicity of doxorubicin against the MDA-MB-231 cancer cell line. Therefore, 10c could be used as a new lead compound for therapeutic development.

  DOI：

  10.1016/j.ejmech.2010.02.035

文献信息

• Cytotoxic N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides: Structure–activity relationships and synergistic studies
  作者：Chiao-Ting Yen、Chin-Chung Wu、Jin-Ching Lee、Shu-Li Chen、Susan L. Morris-Natschke、Pei-Wen Hsieh、Yang-Chang Wu

  DOI：10.1016/j.ejmech.2010.02.035

  日期：2010.6

  The synthesis and cytotoxic evaluation of a series of Fmoc-based dipeptides are described. Among the thirty compounds, 4a, 8a, 12a, 2b, 4b, 10b, 3c, 4c and 6c showed potent activity against HepG2, Hep3B, MCF-7, MDA-MB-231, A549 and Ca9-22 human cancer cell lines. The most active compounds (10a and 10c) showed relatively good sensitivity toward HepG2 and Ca9-22 cell lines with IC(50) values of 1 0 and 0 4 mu M, respectively. Additionally, compound 10c was threefold more potent than doxorubicin, the positive control, against the Ca9-22 cell line. Furthermore, 10c showed a synergistic effect and increased the cytotoxicity of doxorubicin against the MDA-MB-231 cancer cell line. Therefore, 10c could be used as a new lead compound for therapeutic development.