3,6-diethoxycarbonylaminoacridine | 503853-12-1

• 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: 3,6-diethoxycarbonylaminoacridine
• 英文别名: ethyl N-[6-(ethoxycarbonylamino)acridin-3-yl]carbamate
• CAS: 503853-12-1
• 化学式: C₁₉H₁₉N₃O₄
• 分子量: 353.378
• InChiKey: ODPBCOQXWCPLSC-UHFFFAOYSA-N

物化性质

• 沸点：
  486.6±15.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-diethoxycarbonylaminoacridine 在 sodium hydroxide 、 甲烷磺酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 6,20-Dioxa-2,8,18-triazapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1,3(12),4(9),10,13,15,17(22)-heptaene
  参考文献：
  名称：

  4-Hydroxymethyl-3-aminoacridine Derivatives as a New Family of Anticancer Agents

  摘要：

  3-Amino- and 3-alkylamino-4-hydroxymethylacridines bearing various substituents on the C ring have been prepared by regioselective electrophilic aromatic substitution of the corresponding 3-aminoacridines and ring opening of the dihydrooxazinoacridine key intermediates. Most of the new compounds show potent cytotoxic activities against murine L1210 (leukemia), human A549 (lung), and HT29 (colon) cancer cell lines. The most cytotoxic molecules, 1 and 13, are active at nanomolar concentrations. As predicted for acridine derivatives, the new compounds intercalate in DNA, but interestingly they do not interfere with topoisomerase I and II activities. The mode of action remains uncertain because intracellular distribution indicated very different behaviors for 1 and 13. Compound 13 is uniformly distributed in the cell both in the cytoplasm and in the nucleus, whereas compound 1 is essentially localized in cytoplasmic granules.

  DOI：

  10.1021/jm020389w
• 作为产物：
  描述：

  盐酸原黄素 、 氯甲酸乙酯 在 吡啶 作用下， 以78%的产率得到3,6-diethoxycarbonylaminoacridine
  参考文献：
  名称：

  Studies on the interactions of 3,6-diaminoacridine derivatives with human serum albumin by fluorescence spectroscopy

  摘要：

  本研究报告了从丙黄嘌呤中得到的两种对称的 3,6-二氨基吖啶衍生物（3,6-二苯氧羰基氨基吖啶和 3,6-二乙氧羰基氨基吖啶）的制备过程以及它们与人血清白蛋白（HSA）的结合模式。在 pH 值为 7.2 和不同温度下，利用荧光淬灭和紫外可见吸收光谱研究了 HSA 与这些衍生物的相互作用。结果表明，所使用的衍生物能与 HSA 发生强烈的相互作用，并形成 HSA 衍生物复合物，疏水相互作用是稳定每种复合物的主要分子间作用力。计算了不同温度下的 Stern-Volmer 淬火常数、结合常数、结合位点和相应的热力学参数 ΔH、ΔS 和 ΔG。根据佛斯特非辐射能量转移理论，得到了供体（HSA）与受体（3,6-二乙氧羰基氨基吖啶、3,6-二苯氧羰基氨基吖啶和丙黄嘌呤）之间的结合距离（r）～3 nm。此外，还计算了在白蛋白存在下衍生物的检出限和定量限。Copyright © 2014 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/bio.2635

文献信息

• Studies on the interactions of 3,6-diaminoacridine derivatives with human serum albumin by fluorescence spectroscopy
  作者：Elmas Gökoğlu、Fulya Kıpçak、Zeynel Seferoğlu

  DOI：10.1002/bio.2635

  日期：2014.11

  This study reports the preparation and investigation of the modes of binding of the two symmetric 3,6-diaminoacridine derivatives obtained from proflavine, which are 3,6-diphenoxycarbonyl aminoacridine and 3,6-diethoxycarbonyl aminoacridine to human serum albumin (HSA). The interaction of HSA with the derivatives was investigated using fluorescence quenching and ultraviolet-visible absorption spectra at pH 7.2 and different temperatures. The results suggest that the derivatives used can interact strongly with HSA and are the formation of HSA-derivative complexes and hydrophobic interactions as the predominant intermolecular forces in stabilizing for each complex. The Stern-Volmer quenching constants, binding constants, binding sites and corresponding thermodynamic parameters ΔH, ΔS and ΔG were calculated at different temperatures. The binding distance (r) ~ 3 nm between the donor (HSA) and acceptors (3,6-diethoxycarbonyl aminoacridine, 3,6-diphenoxycarbonyl aminoacridine and proflavine) was obtained according to Förster's non-radiative energy transfer theory. Moreover, the limit of detection and limit of quantification of derivatives were calculated in the presence of albumin. Copyright © 2014 John Wiley & Sons, Ltd.

  本研究报告了从丙黄嘌呤中得到的两种对称的 3,6-二氨基吖啶衍生物（3,6-二苯氧羰基氨基吖啶和 3,6-二乙氧羰基氨基吖啶）的制备过程以及它们与人血清白蛋白（HSA）的结合模式。在 pH 值为 7.2 和不同温度下，利用荧光淬灭和紫外可见吸收光谱研究了 HSA 与这些衍生物的相互作用。结果表明，所使用的衍生物能与 HSA 发生强烈的相互作用，并形成 HSA 衍生物复合物，疏水相互作用是稳定每种复合物的主要分子间作用力。计算了不同温度下的 Stern-Volmer 淬火常数、结合常数、结合位点和相应的热力学参数 ΔH、ΔS 和 ΔG。根据佛斯特非辐射能量转移理论，得到了供体（HSA）与受体（3,6-二乙氧羰基氨基吖啶、3,6-二苯氧羰基氨基吖啶和丙黄嘌呤）之间的结合距离（r）～3 nm。此外，还计算了在白蛋白存在下衍生物的检出限和定量限。Copyright © 2014 John Wiley & Sons, Ltd. All Rights Reserved.
• 4-Hydroxymethyl-3-aminoacridine Derivatives as a New Family of Anticancer Agents
  作者：Franck Charmantray、Martine Demeunynck、Danièle Carrez、Alain Croisy、Amélie Lansiaux、Christian Bailly、Pierre Colson

  DOI：10.1021/jm020389w

  日期：2003.3.1

  3-Amino- and 3-alkylamino-4-hydroxymethylacridines bearing various substituents on the C ring have been prepared by regioselective electrophilic aromatic substitution of the corresponding 3-aminoacridines and ring opening of the dihydrooxazinoacridine key intermediates. Most of the new compounds show potent cytotoxic activities against murine L1210 (leukemia), human A549 (lung), and HT29 (colon) cancer cell lines. The most cytotoxic molecules, 1 and 13, are active at nanomolar concentrations. As predicted for acridine derivatives, the new compounds intercalate in DNA, but interestingly they do not interfere with topoisomerase I and II activities. The mode of action remains uncertain because intracellular distribution indicated very different behaviors for 1 and 13. Compound 13 is uniformly distributed in the cell both in the cytoplasm and in the nucleus, whereas compound 1 is essentially localized in cytoplasmic granules.