2-(3-Chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-2-methyl-malonic acid diethyl ester | 181257-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-Chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-2-methyl-malonic acid diethyl ester
• 英文别名: Diethyl (3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)(methyl)propanedioate；diethyl 2-(3-chloro-1,4-dioxonaphthalen-2-yl)-2-methylpropanedioate
• CAS: 181257-38-5
• 化学式: C₁₈H₁₇ClO₆
• 分子量: 364.782
• InChiKey: YARBNBCNDZRZBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-4-Aminocyclohexanol 、 2-(3-Chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-2-methyl-malonic acid diethyl ester 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 23.0h， 以39%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：

  2,3-二氯-1,4-萘醌 、 甲基丙二酸二乙酯 在 sodium amide 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以35%的产率得到2-(3-Chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-2-methyl-malonic acid diethyl ester
  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.