dimethyl 7-oxo-7H-dibenzoquinoline-4,5-dicarboxylate | 125442-44-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: dimethyl 7-oxo-7H-dibenzoquinoline-4,5-dicarboxylate
• 英文别名: dimethyl 7H-dibenzo[de,g]quinolin-7-one-4,5-dicarboxylate；dimethyl 7-oxo-7H-dibenzo[de,g]quinoline-4,5-dicarboxylate；dimethyl 8-oxo-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene-11,12-dicarboxylate
• CAS: 125442-44-6
• 化学式: C₂₀H₁₃NO₅
• 分子量: 347.327
• InChiKey: RVPMFDPCWCOVOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  82.56
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl 7-oxo-7H-dibenzoquinoline-4,5-dicarboxylate 在 氯化亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 苯 为溶剂， 反应 30.5h， 生成 N⁴,N⁵-bis(2-morpholinoethyl)-7-oxo-7H-dibenzo[de,g]quinoline-4,5-dicarboxamide
  参考文献：
  名称：

  Design, synthesis and anticancer activity of oxoaporphine alkaloid derivatives

  摘要：

  A series of new oxoaporphine derivatives were synthesized and their inhibitory activity of topoisomerase I, cytotoxicity and DNA-binding properties were studied. Oxoaporphine can strongly inhibit topoisomerase I at concentrations of 5-50 µM and the cytotoxicity of the derivatives are more potent than their lead compound. Hypochromism, broadening and red shift in the absorption spectra were observed when these compounds bind to calf thymus DNA (CT DNA). These spectral characteristics were consistent with the intercalative binding of these compounds.

  DOI：

  10.3109/14756366.2013.845818
• 作为产物：
  描述：

  10-(methoxyimino)phenanthren-9-one 、 丁炔二酸二甲酯 以10%的产率得到
  参考文献：
  名称：

  NICOLAIDES, D. N.;PAPAGEORGIOU, G. K.;STEPHANIDOU-STEPHANATOU, J., TETRAHERDON, 45,(1989) N4, C. 4585-4592

  摘要：

  DOI：

文献信息

• Synthesis, biological evaluation and molecular modeling of oxoisoaporphine and oxoaporphine derivatives as new dual inhibitors of acetylcholinesterase/butyrylcholinesterase
  作者：Huang Tang、Yong-Biao Wei、Chi Zhang、Fang-Xian Ning、Wei Qiao、Shi-Liang Huang、Lin Ma、Zhi-Shu Huang、Lian-Quan Gu

  DOI：10.1016/j.ejmech.2009.01.021

  日期：2009.6

  synthesized as acetylcholinesterase (AChE) and/or butyrylcholinesterase (BuChE) inhibitors. The AChE inhibition potency of synthetic oxoaporphine derivatives was decreased about 2–3 orders of magnitude as compared with that of oxoisoaporphine derivatives. Non-competitive binding mode was found for both kinds of derivatives. Molecular docking simulations on the oxoisoaporphine derivatives 7 series and

  从中草药中分离出的Aporphine生物碱是重要的天然产物。我们最近报道说，氧代异aphophine生物碱的合成衍生物比BuChE表现出较高的乙酰胆碱酯酶抑制活性和对AChE的高选择性（Bioorg。Med。Chem。Lett。2007，17，3765-3768）。本文提出了进一步的研究结果。一系列新的氧杂卟啉生物碱衍生物（5a - j，4-羧酸酰胺-7-氧代-7 H-二苯并[ de，g ]喹啉，Ar-CONH（CH 2）n NR）及其季me盐（6a – h，Ar-CONH（CH 2）n N+（CH 3）RI -设计和为乙酰胆碱酯酶和/或丁酰胆碱酯酶（BuChE的）抑制剂合成）。合成的氧磷卟啉衍生物的AChE抑制能力与氧代异吗啡衍生物相比降低了约2-3个数量级。两种衍生物都发现了非竞争性结合模式。氧代异aporphine衍生物7系列和oxoaporphine衍生物6系列与来自加州鱼雷的AC
• Synthesis of some fused pyridine-and oxazole-polycyclic systems from 10-(methoxyimino)phenanthren-9-one
  作者：D.N. Nlcolaides★、G.K. Papageorgiou、J. Stephanidou-Stephanatou

  DOI：10.1016/s0040-4020(01)89093-1

  日期：——
• NICOLAIDES, D. N.;PAPAGEORGIOU, G. K.;STEPHANIDOU-STEPHANATOU, J., TETRAHERDON, 45,(1989) N4, C. 4585-4592
  作者：NICOLAIDES, D. N.、PAPAGEORGIOU, G. K.、STEPHANIDOU-STEPHANATOU, J.

  DOI：——

  日期：——
• Design, synthesis and anticancer activity of oxoaporphine alkaloid derivatives
  作者：Yong-Biao Wei、Ying-Xin Li、Hui Song、Xian-Jin Feng

  DOI：10.3109/14756366.2013.845818

  日期：2014.10.1

  A series of new oxoaporphine derivatives were synthesized and their inhibitory activity of topoisomerase I, cytotoxicity and DNA-binding properties were studied. Oxoaporphine can strongly inhibit topoisomerase I at concentrations of 5-50 µM and the cytotoxicity of the derivatives are more potent than their lead compound. Hypochromism, broadening and red shift in the absorption spectra were observed when these compounds bind to calf thymus DNA (CT DNA). These spectral characteristics were consistent with the intercalative binding of these compounds.