6H-isoquinolino[2,3-a]quinazoline-5,12-dione | 500198-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6H-isoquinolino[2,3-a]quinazoline-5,12-dione
• 英文别名: 5H-isoquino[2,3-a]quinazoline-5,12(6H)-dione
• CAS: 500198-60-7
• 化学式: C₁₆H₁₀N₂O₂
• 分子量: 262.268
• InChiKey: ZOLCCYQLJANRBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[(4-oxo-3,4-dihydro-2-quinazolinyl)methyl]benzoic acid 在 乙酸酐 作用下， 以90%的产率得到6H-isoquinolino[2,3-a]quinazoline-5,12-dione
  参考文献：
  名称：

  Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′: 5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives

  摘要：

  Treatment of 2-(4-oxo-3,4-dihydrothieno[2,3-d]-and-[3,2-d]pyrimidin-2-ylmethyl)benzoic acids and 2-(4-oxo-3,4-dihydro-2-quinazolinylmethyl)benzoic acid with acetic anhydride gave thieno[3',2':5,6]-and-[2',3':5,6]pyrimido[1,2-b]isoquinoline-4,11-diones and isoquino[2,3-a]quinazoline-5,12-dione respectively. NMR spectroscopy showed that an intramolecular acylation of the above acids occurs at the atom N-1 of the pyrimidinone part of the bicycle.

  DOI：

  10.1007/s10593-008-0119-0

文献信息

• Efficient MW-Assisted Synthesis of Some New Isoquinolinone Derivatives With<i>In Vitro</i>Antitumor Activity
  作者：Mohamed H. Hekal、Fatma S. M. Abu El-Azm

  DOI：10.1002/jhet.2916

  日期：2017.11

  An efficient and convenient synthesis of novel [1,3]oxazino[3,2‐b]isoquinoline‐5,12‐dione derivative 4 was achieved by the reaction of anthranilic acid with homophthalic anhydride under microwave irradiation, followed by cyclization with acetic anhydride. Some new isoquinolinone and fused isoquinolinone derivatives were prepared via reaction of compound 4 with different nitrogen nucleophiles by using

  在微波辐射下，邻氨基苯甲酸与高邻苯二甲酸酐反应，然后再与乙酸酐环合，从而可以高效，方便地合成新型[1,3]恶嗪[3,2-b]异喹啉-5,12-二酮衍生物4。通过使用回流和聚焦微波反应器，通过化合物4与不同的氮亲核试剂反应，制备了一些新的异喹啉酮和稠合的异喹啉酮衍生物。微波辐射有利于所需产物的形成，具有提高的产率和缩短的反应时间。这是合成异喹啉酮衍生物的简单而绿色的方法。制备的化合物的结构通过IR，1阐明H-NMR和质谱。一些新制备的化合物在体外针对一组三种人类肿瘤细胞系进行了测试，即肝细胞癌（肝）HepG2，结肠癌HCT-116和乳腺乳腺癌MCF-7。几乎所有测试的化合物均显示令人满意的活性。
• Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′: 5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives
  作者：A. V. Zadorozhny、V. A. Kovtunenko、A. V. Turov、T. T. Kucherenko

  DOI：10.1007/s10593-008-0119-0

  日期：2008.7

  Treatment of 2-(4-oxo-3,4-dihydrothieno[2,3-d]-and-[3,2-d]pyrimidin-2-ylmethyl)benzoic acids and 2-(4-oxo-3,4-dihydro-2-quinazolinylmethyl)benzoic acid with acetic anhydride gave thieno[3',2':5,6]-and-[2',3':5,6]pyrimido[1,2-b]isoquinoline-4,11-diones and isoquino[2,3-a]quinazoline-5,12-dione respectively. NMR spectroscopy showed that an intramolecular acylation of the above acids occurs at the atom N-1 of the pyrimidinone part of the bicycle.
• Condensed isoquinolines. 35*. Synthesis and reactions of 4h-thieno[3′,4′:5,6]pyrimido-[1,2-b]isoquinoline-4,11(5H)-dione
  作者：A. V. Zadorozhny、V. A. Kovtunenko、A. V. Turov

  DOI：10.1007/s10593-010-0608-9

  日期：2010.12

  Derivatives of the previously unknown tetracyclic system 4H-thieno[3',4':5,6] pyrimido[1,2-b]isoquinoline- 4,11(5H)-dione have been synthesized. A comparison of the spectral characteristics and the biological activities of these compounds has been carried out, and also of their positional isomers and benzene isosteres. The differences, associated with the position of the sulfur atom, are most reflected in their electronic spectra.