4-ethylspiro[(dihydropyrazin-2,5-dione)-6,3'-(2,3-dihydrothieno[2,3-b]naphtho-4',9'-dione)] | 1027000-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-ethylspiro[(dihydropyrazin-2,5-dione)-6,3'-(2,3-dihydrothieno[2,3-b]naphtho-4',9'-dione)]
• 英文别名: 1'-ethylspiro[2H-benzo[f][1]benzothiole-3,3'-piperazine]-2',4,5',9-tetrone
• CAS: 1027000-76-5
• 化学式: C₁₇H₁₄N₂O₄S
• 分子量: 342.375
• InChiKey: HYJCHOMIKZPEFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三乙胺 作用下， 以 甲醇 为溶剂， 生成 4-ethylspiro[(dihydropyrazin-2,5-dione)-6,3'-(2,3-dihydrothieno[2,3-b]naphtho-4',9'-dione)]
  参考文献：
  名称：

  Spiro[(dihydropyrazin-2,5-dione)-6,3′-(2′,3′-dihydrothieno[2,3-b]naphtho-4′,9′-dione)]-Based Cytotoxic Agents: Structure–Activity Relationship Studies on the Substituent at N4-Position of the Diketopiperazine Domain

  摘要：

  Analogues of the previously reported potent cytotoxic spiro[(dihydropyrazine-2,5-dione)-6,3'-(2',3'-dihydrothieno[2,3-b]naphtho-4',9'-dione)] derivatives (3, 3') were prepared to explore new structural requirements at the diketopiperazine domain for the cytotoxic activity. The in vitro activity was evaluated against the MCF-7 human breast carcinoma and SW 620 human colon carcinoma cell lines. The 4-[(2-N,N-dimethyl)amino]ethyl (6i), and the 4-(2-pyrrolydin)ethyl (61) derivatives emerged as the most potent compounds of this series, with a cytotoxic activity comparable to that of doxorubicin. These compounds, in both racemic and pure enantiomeric forms, showed also a high efficacy in cell lines resistant to doxorubicin (MCF-7/Dx) and in cell lines that were highly resistant to treatment with doxorubicin, such as HEK-293 (kidney), M-14 (melanoma), and HeLa (cervical adenocarcinoma) human cell lines. In addition, the effects on growth and cell cycle progression in CaCo-2 cell fine (colon adenocarcinoma) and DNA-binding properties were investigated.

  DOI：

  10.1021/jm7013056