7,15-Dihydro-pyrazino<2,1-b:5,4-b'>dichinazolin-5,13-dion | 86942-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7,15-Dihydro-pyrazino<2,1-b:5,4-b'>dichinazolin-5,13-dion
• 英文别名: 6,14-dihydropyrazino[2,1-b:5,4-b']diquinazoline-8,16-dione；7,15-dihydropyrazino[2,1-b:5,4-b']diquinazoline-5,13-dione；pyrazino[2,1-b:5,4-b']diquinazoline-8,16(6H,14H)-dione；pyrazine[2,1-b;5,4-b]diquinazolin-8,16(6H,14H)-dione；7,15-Dihydro-pyrazino[2,1-b:5,4-b']dichinazolin-5,13-dion；1,4,12,15-tetrazapentacyclo[12.8.0.03,12.05,10.016,21]docosa-3,5,7,9,14,16,18,20-octaene-11,22-dione
• CAS: 86942-22-5
• 化学式: C₁₈H₁₂N₄O₂
• 分子量: 316.319
• InChiKey: PBMQZYWPBFMEPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  569.4±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(bromomethyl)-4(3H)-quinazolinone 在 碳酸氢钠 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以88%的产率得到7,15-Dihydro-pyrazino<2,1-b:5,4-b'>dichinazolin-5,13-dion
  参考文献：
  名称：

  Aryne Insertion Reactions Leading to Bioactive Fused Quinazolinones: Diastereoselective Total Synthesis of Cruciferane

  摘要：

  Insertion reactions of an in situ generated arynes to a variety of suitably substituted 1,3-quinazolin-4-ones have been demonstrated for a new efficient one-step approach to a diverse range of fused quinazolinone architectures. The present protocol has been effectively utilized to accomplish the concise total synthesis of recently isolated bioactive natural products tryptanthrin, phaitanthrins A-C, and cruciferane.

  DOI：

  10.1021/ol4018062

文献信息

• Microwave-Assisted, Solvent-Free Synthesis of Several Quinazoline Alkaloid Frameworks
  作者：J. Menéndez、Pilar Cledera、Juan Sánchez、Esmeralda Caballero、Tamara Yates、Elena Ramírez、Carmen Avendaño、M. Ramos

  DOI：10.1055/s-2007-990818

  日期：2007.11

  Microwave irradiation leads to a considerable improvement of the cyclocondensation between anthranilic acid and lactim ethers derived from piperazine-2,5-diones in terms of reaction times, yields, and stereocenter integrity. This reaction has been used to prepare some derivatives of the pyrazino[2,1-b]quinazoline-3,6-dione system present in many quinazoline alkaloids. It could also be applied to the synthesis of compounds containing the complete hexacyclic ring system of the anti-MDR natural product N-acetyl­ardeemin, and other comprising the pentacyclic framework of circumdatin E. The microwave-assisted reaction was also much better than the thermal one when applied to a bis-lactim ether, leading to the corresponding pentacyclic pyrazino[2,1-b:5,4-b′]diquinazoline-8,16-dione in excellent yield.

  微波辐照显著改善了邻氨基苯甲酸与来自哌嗪-2,5-二酮的乳酰亚胺醚之间的环加成反应，在反应时间、产率和立体中心完整性方面均有显著提升。该反应已被用于制备多种喹唑啉生物碱中存在的吡嗪并[2,1-b]喹唑啉-3,6-二酮系统的衍生物。它还可以应用于合成含有抗多药耐药天然产物N-乙酰基阿德米宁的完整六环体系化合物，以及其他包含circumdatin E的五环框架的化合物。微波辅助反应在应用于双乳酰亚胺醚时也比热反应更为高效，得到了对应的五环吡嗪并[2,1-b:5,4-b′]双喹唑啉-8,16-二酮，产率极佳。
• Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones
  作者：Mohamed A. Ameen、Essam Kh. Ahmed、Mohamed Ramadan、Hisham A. Abd El-Naby、Asmaa A. Abdel-Haseeb

  DOI：10.1007/s00706-017-1961-5

  日期：2017.8

  spectral analysis, screened for their anticancer activity at a concentration of 10 μΜ against a panel of 56 cell lines derived from nine different types of cancers, including leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. The synthesized compounds screened for their PDE 5 inhibitory activity and it showed encouraged activity compared to sildenafil. Graphical abstract

  摘要合成了一系列新颖的螺取代的2,3-二氢喹唑啉-4（1 H）-酮，并通过光谱分析在结构上进行了确认，以10μM的浓度筛选了它们对一组源自9种细胞的56种细胞系的抗癌活性不同类型的癌症，包括白血病，黑素瘤，肺癌，结肠癌，中枢神经系统，卵巢癌，肾癌，前列腺癌和乳腺癌。合成的化合物筛选了其PDE 5抑制活性，与西地那非相比显示出令人鼓舞的活性。 图形概要
• Solvent-Free Cyclocondensation of Lactim Ethers with Anthranilic Acid under Microwave Irradiation
  作者：J. Carlos Menéndez、Pilar Cledera、J. Domingo Sánchez、Esmeralda Caballero、Carmen Avendaño、M. Teresa Ramos

  DOI：10.1055/s-2004-817784

  日期：——

  Microwave irradiation greatly improves the results of the cyclocondensation between anthranilic acid and lactim ethers derived from 2,5-piperazinediones in terms of reaction times, yields and stereocenter integrity, leading to pyrazino[2,1-b]quinazoline-3,6-diones. The microwave-assisted reaction was also much better than the thermal one when applied to a bis-lactim ether, leading to the corresponding pentacyclic pyrazino [2,1-b:5,4-b′]diquinazol­ine-5,13-dione in excellent yield, and it also improved the preparation of compounds containing the ring system of the anti-MDR natural product N-acetylardeemin.

  微波辐射极大地改善了邻氨基苯甲酸与2,5-哌嗪二酮衍生的内酰亚胺之间的环缩合反应时​​间、产率和立构中心完整性，从而生成吡嗪并[2,1-b]喹唑啉-3,6-二酮。当应用于双内酰亚胺醚时，微波辅助反应也比热反应好得多，导致在优良的收率，同时也改进了抗MDR天然产物N-乙酰葆明含环体系​​化合物的制备。
• Gompper, Rudolf; Breitschaft, Walter, Angewandte Chemie, 1983, vol. 95, # 9, p. 727 - 729
  作者：Gompper, Rudolf、Breitschaft, Walter

  DOI：——

  日期：——
• Reddy, L. Manmohan; Reddy, P. Pratap; Reddy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 9, p. 2119 - 2120
  作者：Reddy, L. Manmohan、Reddy, P. Pratap、Reddy

  DOI：——

  日期：——