(1,4-dioxo-1,4-dihydro-naphthalene-2,3-diyl)-di-malonic acid tetraethyl ester | 569321-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1,4-dioxo-1,4-dihydro-naphthalene-2,3-diyl)-di-malonic acid tetraethyl ester
• 英文别名: (1,4-Dioxo-1,4-dihydro-naphthalin-2,3-diyl)-di-malonsaeure-tetraaethylester；Naphthochinon-(1.4)-dimalonsaeure-(2.3)-tetraaethylester
• CAS: 569321-99-9
• 化学式: C₂₄H₂₆O₁₀
• 分子量: 474.464
• InChiKey: ALCGYYGHOVCRHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  139.34
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1,4-dioxo-1,4-dihydro-naphthalene-2,3-diyl)-di-malonic acid tetraethyl ester 在 乙醇 、 sodium ethanolate 作用下， 生成 2,4,9-trioxo-1,3,4,9-tetrahydro-cyclopenta[b]naphthalene-1,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Liebermann, Chemische Berichte, 1900, vol. 33, p. 570

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二溴-1,4-萘醌 、 sodium diethylmalonate 在 乙醇 作用下， 生成 (1,4-dioxo-1,4-dihydro-naphthalene-2,3-diyl)-di-malonic acid tetraethyl ester
  参考文献：
  名称：

  Liebermann, Chemische Berichte, 1900, vol. 33, p. 570

  摘要：

  DOI：

文献信息

• Synthesis and cytotoxicity evaluation of 2-amino- and 2-hydroxy-3-ethoxycarbonyl- N -substituted-benzo[ f ]indole-4,9-dione derivatives
  作者：Hyun-Jung Lee、Myung-Eun Suh、Chong-Ock Lee

  DOI：10.1016/s0968-0896(03)00062-2

  日期：2003.4

  Reaction between 2,3-dichloronaphthoquinone (I) and ethyl cyanoacetate or diethyl malonate under different conditions gave the starting materials, 2-chloro-3-(alpha-cyano-alpha-ethoxycarbonyl-methyl)-1,4-naphthoquinone (A) or 2-chloro-3-(diethoxycarbonyl-methyl)-1,4-naphthoquinone (B). The 2-amino-3-ethoxycarbonyl-N-substituted-benzo[f]indole-4,9-dione derivatives [A-(1-10)] and 2-hydroxy-3-ethoxycarbonyl-N-substituted-benzo[f]indole-4,9-dione derivatives [B-(1-12)] were prepared from compounds A and B, respectively, by using various alkyl-, and arylamines. The cytotoxic activities of the prepared compounds were evaluated by SRB (Sulforhodamine B) assay against the following tumor cell lines: A459 (human lung), SK-OV-3 (human ovarian), SK-MEL-2 (human melanoma), XF498 (human CNS), and HCT 15 (human colon). Many of the derivatives mentioned exhibited more potent cytotoxic effects against SK-OV-3 and XF498 than etoposide. Significantly, 2-amino-3-ethoxycarbonyl-N-(3-methyl-phenyl)-benzo[f]indole-4,9-dione (A-8) showed potent activity against all tumor cell lines, and in particular, its cytotoxic effect against SK-OV-3 was much higher than doxorubicin. (C) 2003 Elsevier Science Ltd. All rights reserved.