4-oxo-4,7-dihydro-1H-pyrrolo[2,3-h]quinoline-3-carboxylic acid | 852715-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-oxo-4,7-dihydro-1H-pyrrolo[2,3-h]quinoline-3-carboxylic acid
• 英文别名: 4-Oxo-1,7-dihydropyrrolo[2,3-h]quinoline-3-carboxylic acid
• CAS: 852715-64-1
• 化学式: C₁₂H₈N₂O₃
• 分子量: 228.207
• InChiKey: DHWRGLJKKIKAQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxo-4,7-dihydro-1H-pyrrolo[2,3-h]quinoline-3-carboxylic acid 以 二苯醚 为溶剂， 反应 0.33h， 以80%的产率得到1H,7H-Pyrrolo[2,3-h]quinolin-4-one
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Antitumor Activity of 2-Phenylpyrroloquinolin-4-ones

  摘要：

  In our search for potential new anticancer drugs, we designed and synthesized a series of tricyclic compounds containing the antimitotic 2-phenylazaflavone chromophore fused to a pyrrole ring in a pyrroloquinoline structure. Compounds 8, 18, 19, 22, 23, 25 and 26, when tested against a panel of fourteen human tumor cell lines, showed poor in vitro cytotoxic activity, whereas 20, 21 and 24 showed significant activity (IC50 0.7 to 50 mu M). Steroid hormone-sensitive ovary, liver, breast and adrenal gland adenocarcinoma cell lines displayed the highest sensitivity (IC50 0.7 to 8,mu M). Compound 24 blocked cells in the G(2)/M phase of the cell cycle and induced a significant increase in apoptotis. Compounds 20, 21 and 24 proved to alter microtubule assembly and stability, displaying a cytoplasmic microtubule network similar to that caused by Vincristine. In vivo, administration of compound 24 to Balb/c mice inhibited the growth of a syngenic hepatocellular carcinoma.

  DOI：

  10.1021/jm049387x
• 作为产物：
  描述：

  2,6-二硝基甲苯 在 盐酸 、 sodium hydroxide 、 titanium(III) chloride 作用下， 以 二苯醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.33h， 生成 4-oxo-4,7-dihydro-1H-pyrrolo[2,3-h]quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Antitumor Activity of 2-Phenylpyrroloquinolin-4-ones

  摘要：

  In our search for potential new anticancer drugs, we designed and synthesized a series of tricyclic compounds containing the antimitotic 2-phenylazaflavone chromophore fused to a pyrrole ring in a pyrroloquinoline structure. Compounds 8, 18, 19, 22, 23, 25 and 26, when tested against a panel of fourteen human tumor cell lines, showed poor in vitro cytotoxic activity, whereas 20, 21 and 24 showed significant activity (IC50 0.7 to 50 mu M). Steroid hormone-sensitive ovary, liver, breast and adrenal gland adenocarcinoma cell lines displayed the highest sensitivity (IC50 0.7 to 8,mu M). Compound 24 blocked cells in the G(2)/M phase of the cell cycle and induced a significant increase in apoptotis. Compounds 20, 21 and 24 proved to alter microtubule assembly and stability, displaying a cytoplasmic microtubule network similar to that caused by Vincristine. In vivo, administration of compound 24 to Balb/c mice inhibited the growth of a syngenic hepatocellular carcinoma.

  DOI：

  10.1021/jm049387x

文献信息

• Synthesis and in Vitro and in Vivo Antitumor Activity of 2-Phenylpyrroloquinolin-4-ones
  作者：Maria Grazia Ferlin、Gianfranco Chiarelotto、Venusia Gasparotto、Lisa Dalla Via、Vincenzo Pezzi、Luisa Barzon、Giorgio Palù、Ignazio Castagliuolo

  DOI：10.1021/jm049387x

  日期：2005.5.1

  In our search for potential new anticancer drugs, we designed and synthesized a series of tricyclic compounds containing the antimitotic 2-phenylazaflavone chromophore fused to a pyrrole ring in a pyrroloquinoline structure. Compounds 8, 18, 19, 22, 23, 25 and 26, when tested against a panel of fourteen human tumor cell lines, showed poor in vitro cytotoxic activity, whereas 20, 21 and 24 showed significant activity (IC50 0.7 to 50 mu M). Steroid hormone-sensitive ovary, liver, breast and adrenal gland adenocarcinoma cell lines displayed the highest sensitivity (IC50 0.7 to 8,mu M). Compound 24 blocked cells in the G(2)/M phase of the cell cycle and induced a significant increase in apoptotis. Compounds 20, 21 and 24 proved to alter microtubule assembly and stability, displaying a cytoplasmic microtubule network similar to that caused by Vincristine. In vivo, administration of compound 24 to Balb/c mice inhibited the growth of a syngenic hepatocellular carcinoma.