diethyl 4,6-dichloro-10-methylpyrido[3,2-g]quinoline-3,7-dicarboxylate | 913957-95-6

• 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: diethyl 4,6-dichloro-10-methylpyrido[3,2-g]quinoline-3,7-dicarboxylate
• 英文别名: Diethyl 4,6-dichloro-10-methylpyrido[3,2-g]quinoline-3,7-dicarboxylate
• CAS: 913957-95-6
• 化学式: C₁₉H₁₆Cl₂N₂O₄
• 分子量: 407.253
• InChiKey: CEAKPCQWYHDDAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4,6-dichloro-10-methylpyrido[3,2-g]quinoline-3,7-dicarboxylate 在 ammonium hydroxide 作用下， 反应 8.0h， 以56%的产率得到diethyl 4,6-diamino-10-Methylpyrido[3,2-g]quinoline-3,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of certain pyrido[3,2-g]quinoline derivatives

  摘要：

  The present report describes the synthesis and evaluation of tricyclic pyrido[3,2-g]quinoline derivatives in which an additional pyridine ring is linearly fused on the antibacterial quinoline-3-carboxylic acid. Among them, only diethyl 4,6-diamino-10-methylpyrido[3,2-g]quinoline-3,7-dicarboxylate (9a) and diethyl 4,6-bis-(3-dimethylaminopropylamino)-10-methylpyrido[3,2g]quinoline-3,7-dicarboxylate (9d) were able to completely inhibit cell proliferation of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS) implying either amino or dimethylaminopropyl moiety at C-4 and C-6 positions is crucial for the antiproliferative activity of pyrido[3,2-g]quinoline derivatives. Compounds 9a-9d were further evaluated for their activity against the growth of MCF-7 and two prostate cancer cell lines, LNCaP and PC-3. Results indicated the antiproliferative activity decreased in an order 9d > 9a >> 9b and 9c. Compound 9d was the most cytotoxic with an IC50 value of 5.63 and 3.96 mu M, respectively, against LNCaP and MCF-7. Flow cytometric analyses revealed that growth inhibition of LNCaP by 9d was due to cell cycle arrest in G1 phase, and followed by apoptosis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.030
• 作为产物：
  描述：

  2,6-二氨基甲苯 在 三氯氧磷 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 11.0h， 生成 diethyl 4,6-dichloro-10-methylpyrido[3,2-g]quinoline-3,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of certain pyrido[3,2-g]quinoline derivatives

  摘要：

  The present report describes the synthesis and evaluation of tricyclic pyrido[3,2-g]quinoline derivatives in which an additional pyridine ring is linearly fused on the antibacterial quinoline-3-carboxylic acid. Among them, only diethyl 4,6-diamino-10-methylpyrido[3,2-g]quinoline-3,7-dicarboxylate (9a) and diethyl 4,6-bis-(3-dimethylaminopropylamino)-10-methylpyrido[3,2g]quinoline-3,7-dicarboxylate (9d) were able to completely inhibit cell proliferation of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS) implying either amino or dimethylaminopropyl moiety at C-4 and C-6 positions is crucial for the antiproliferative activity of pyrido[3,2-g]quinoline derivatives. Compounds 9a-9d were further evaluated for their activity against the growth of MCF-7 and two prostate cancer cell lines, LNCaP and PC-3. Results indicated the antiproliferative activity decreased in an order 9d > 9a >> 9b and 9c. Compound 9d was the most cytotoxic with an IC50 value of 5.63 and 3.96 mu M, respectively, against LNCaP and MCF-7. Flow cytometric analyses revealed that growth inhibition of LNCaP by 9d was due to cell cycle arrest in G1 phase, and followed by apoptosis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.030

文献信息

• Synthesis and antiproliferative evaluation of certain pyrido[3,2-g]quinoline derivatives
  作者：Shu-Yu Li、Yeh-Long Chen、Chihuei Wang、Cherng-Chyi Tzeng

  DOI：10.1016/j.bmc.2006.07.030

  日期：2006.11

  The present report describes the synthesis and evaluation of tricyclic pyrido[3,2-g]quinoline derivatives in which an additional pyridine ring is linearly fused on the antibacterial quinoline-3-carboxylic acid. Among them, only diethyl 4,6-diamino-10-methylpyrido[3,2-g]quinoline-3,7-dicarboxylate (9a) and diethyl 4,6-bis-(3-dimethylaminopropylamino)-10-methylpyrido[3,2g]quinoline-3,7-dicarboxylate (9d) were able to completely inhibit cell proliferation of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS) implying either amino or dimethylaminopropyl moiety at C-4 and C-6 positions is crucial for the antiproliferative activity of pyrido[3,2-g]quinoline derivatives. Compounds 9a-9d were further evaluated for their activity against the growth of MCF-7 and two prostate cancer cell lines, LNCaP and PC-3. Results indicated the antiproliferative activity decreased in an order 9d > 9a >> 9b and 9c. Compound 9d was the most cytotoxic with an IC50 value of 5.63 and 3.96 mu M, respectively, against LNCaP and MCF-7. Flow cytometric analyses revealed that growth inhibition of LNCaP by 9d was due to cell cycle arrest in G1 phase, and followed by apoptosis. (c) 2006 Elsevier Ltd. All rights reserved.