5,6-dihydroquinazolino[4,3-b]quinazolin-8-one | 109477-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 嘧啶二氮卓类
• 英文名称: 5,6-dihydroquinazolino[4,3-b]quinazolin-8-one
• 英文别名: 5,6-dihydro-8H-quinazolino[4,3-b]quinazolin-8-one；7-Oxo-5.6-dihydro-7H-5.6a.12-triaza-benzanthracen；8H-Quinazolino[4,3-b]quinazolin-8-one, 5,6-dihydro-
• CAS: 109477-69-2
• 化学式: C₁₅H₁₁N₃O
• 分子量: 249.272
• InChiKey: IWXYHQNHTVFXOI-UHFFFAOYSA-N

物化性质

• 熔点：
  185-186 °C(Solv: ethanol (64-17-5))
• 沸点：
  471.2±48.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

SDS

反应信息

• 作为产物：
  描述：

  N-(2-carbamoylphenyl)-2-nitrobenzamide 在 tin(II) chloride dihdyrate 、 碘 、 1-丁基-3-甲基咪唑溴盐 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 5,6-dihydroquinazolino[4,3-b]quinazolin-8-one
  参考文献：
  名称：

  骆驼宁碱A衍生物及其制备和在防治植物病毒病菌病中的应用

  摘要：

  本发明涉及骆驼宁碱A衍生物I‑1～I‑12及其制备方法和在防治植物病毒病菌病中的应用。本发明的色胺酮类衍生物I‑1～I‑12显示出抗植物病毒活性，能很好地抑制烟草花叶病毒，同时该类化合物也表现出广谱的抗植物病菌活性，且对苹果轮纹病菌的抑制活性突出。

  公开号：

  CN113999231A

文献信息

• Auto-Redox Reaction:  Tin(II) Chloride-Mediated One-Step Reductive Cyclization Leading to the Synthesis of Novel Biheterocyclic 5,6-Dihydro-quinazolino[4,3-<i>b</i>]quinazolin-8-ones with Three-Point Diversity
  作者：Abhijeet Deb Roy、Arunachalam Subramanian、Raja Roy

  DOI：10.1021/jo0518912

  日期：2006.1.1

  A tin(II) chloride-mediated short, efficient, and practical regioselective synthesis of biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity is reported. A one-step reductive transformation of 2-(2-nitrophenyl)-3H-quinazolin-4-one in various alcohols furnished the desired tetracyclic product in good yields with high purity.
• Luotonin A and Its Derivatives as Novel Antiviral and Antiphytopathogenic Fungus Agents
  作者：Yanan Hao、Kaihua Wang、Ziwen Wang、Yuxiu Liu、Dejun Ma、Qingmin Wang

  DOI：10.1021/acs.jafc.0c04278

  日期：2020.8.19

  Plant diseases caused by viruses and fungi have posed a serious threat to global agricultural production. The discovery of new leads based on natural products is an important way to innovate pesticides. In this work, natural product luotonin A was found to have good antiviral activity against tobacco mosaic virus (TMV) for the first time. A series of luotonin A derivatives were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities systematically. Most compounds displayed better antiviral activities against TMV than commercial ribavirin. Compounds 9k, 12b, and 12d displayed about similar inhibitory effects as ningnanmycin (inhibitory rates of 55, 57, and 59% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively), the best antiviral agent at present, and emerged as novel antiviral leads for further research. We selected 9k for further antiviral mechanism research via transmission electron microscopy and molecular docking, which revealed that compound 9k can interact with TMV coat protein through the hydrogen bond, leading to its polymerization, thus preventing virus assembly. Further fungicidal activity tests showed that these compounds also showed broad-spectrum fungicidal activities against 14 kinds of phytopathogenic fungi. Especially, compound 14 with a 100% antifungal effect against Botrytis cinereal emerged as a lead for further research. This work provides a reference for the development of agricultural active ingredients based on Chinese medicine plants.