7-chloro-6-(1,1-diethoxycarbonyl-ethyl)-5,8-quinolinedione | 648928-14-7

• 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: 7-chloro-6-(1,1-diethoxycarbonyl-ethyl)-5,8-quinolinedione
• 英文别名: Diethyl 2-(7-chloro-5,8-dioxoquinolin-6-yl)-2-methylpropanedioate；diethyl 2-(7-chloro-5,8-dioxoquinolin-6-yl)-2-methylpropanedioate
• CAS: 648928-14-7
• 化学式: C₁₇H₁₆ClNO₆
• 分子量: 365.77
• InChiKey: YKFRHUASGAEBJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  187-188 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  482.1±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙胺 、 7-chloro-6-(1,1-diethoxycarbonyl-ethyl)-5,8-quinolinedione 以 乙醇 为溶剂， 反应 15.0h， 以24%的产率得到
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of pyridin[2,3-f]indole-2,4,9-trione and benz[f]indole-2,4,9-trione derivatives

  摘要：

  3-Ethoxycarbonyl-3-methyl-N-substituted-2,3-dihydro-benz[f]indole-2,4,9-trione [9(a-d)] and 3-ethoxycarbonyl3-methyl-N-substrituted-2,3-dihydro-benz[j]indole-2,4,9-trione [10(a-i)] derivatives were synthesized from 7-chloro-6-(1,1-diethoxycarbonyl-ethyl)-5,8-quinolinedione (7) and 2-chloro-3-(1,1-diethoxycarbonyl-ethyl)-1,4-naphthoquinone (8), respectively, using a variety of alkyl- and arylamines. The cytotoxic activities of the synthesized compounds were evaluated by a Sulforhodamine B (SRB) assay against the following tumor cell lines: A459 (human non-small cell lung), SK-OV-3 (human ovarian), SK-MEL-2 (human melanoma), XF498 (human CNS), and HCT 15 (human colon). Almost all the derivatives mentioned above had a more potent cytotoxic effect against SK-OV-3 than etoposide. In particular, 3-ethoxycarbonyl-3-methyl-N-(4-aminophenyl)-2,3-dihydrobenz[f]indole-2,4,9- trione (10h) exhibited greater activity against all the tumor cell lines, and its cytotoxic effect against SK-OV-3 was especially higher than doxorubicin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.005
• 作为产物：
  描述：

  6,7-二氯-5,8-喹啉二酮 、 甲基丙二酸二乙酯 在 sodium amide 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以22%的产率得到7-chloro-6-(1,1-diethoxycarbonyl-ethyl)-5,8-quinolinedione
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of pyridin[2,3-f]indole-2,4,9-trione and benz[f]indole-2,4,9-trione derivatives

  摘要：

  3-Ethoxycarbonyl-3-methyl-N-substituted-2,3-dihydro-benz[f]indole-2,4,9-trione [9(a-d)] and 3-ethoxycarbonyl3-methyl-N-substrituted-2,3-dihydro-benz[j]indole-2,4,9-trione [10(a-i)] derivatives were synthesized from 7-chloro-6-(1,1-diethoxycarbonyl-ethyl)-5,8-quinolinedione (7) and 2-chloro-3-(1,1-diethoxycarbonyl-ethyl)-1,4-naphthoquinone (8), respectively, using a variety of alkyl- and arylamines. The cytotoxic activities of the synthesized compounds were evaluated by a Sulforhodamine B (SRB) assay against the following tumor cell lines: A459 (human non-small cell lung), SK-OV-3 (human ovarian), SK-MEL-2 (human melanoma), XF498 (human CNS), and HCT 15 (human colon). Almost all the derivatives mentioned above had a more potent cytotoxic effect against SK-OV-3 than etoposide. In particular, 3-ethoxycarbonyl-3-methyl-N-(4-aminophenyl)-2,3-dihydrobenz[f]indole-2,4,9- trione (10h) exhibited greater activity against all the tumor cell lines, and its cytotoxic effect against SK-OV-3 was especially higher than doxorubicin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.005

文献信息

• Synthesis and cytotoxicity evaluation of pyridin[2,3-f]indole-2,4,9-trione and benz[f]indole-2,4,9-trione derivatives
  作者：Hyun-Jung Lee、So-Young Park、Jin Sung Kim、Hyun Min Song、Myung-Eun Suh、Chong-Ock Lee

  DOI：10.1016/j.bmc.2003.08.005

  日期：2003.11

  3-Ethoxycarbonyl-3-methyl-N-substituted-2,3-dihydro-benz[f]indole-2,4,9-trione [9(a-d)] and 3-ethoxycarbonyl3-methyl-N-substrituted-2,3-dihydro-benz[j]indole-2,4,9-trione [10(a-i)] derivatives were synthesized from 7-chloro-6-(1,1-diethoxycarbonyl-ethyl)-5,8-quinolinedione (7) and 2-chloro-3-(1,1-diethoxycarbonyl-ethyl)-1,4-naphthoquinone (8), respectively, using a variety of alkyl- and arylamines. The cytotoxic activities of the synthesized compounds were evaluated by a Sulforhodamine B (SRB) assay against the following tumor cell lines: A459 (human non-small cell lung), SK-OV-3 (human ovarian), SK-MEL-2 (human melanoma), XF498 (human CNS), and HCT 15 (human colon). Almost all the derivatives mentioned above had a more potent cytotoxic effect against SK-OV-3 than etoposide. In particular, 3-ethoxycarbonyl-3-methyl-N-(4-aminophenyl)-2,3-dihydrobenz[f]indole-2,4,9- trione (10h) exhibited greater activity against all the tumor cell lines, and its cytotoxic effect against SK-OV-3 was especially higher than doxorubicin. (C) 2003 Elsevier Ltd. All rights reserved.