2-(azidomethyl)quinazolin-4(3H)-one | 1247556-32-6

• 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: 2-(azidomethyl)quinazolin-4(3H)-one
• 英文别名: 2-(azidomethyl)-3H-quinazolin-4-one
• CAS: 1247556-32-6
• 化学式: C₉H₇N₅O
• 分子量: 201.187
• InChiKey: UTFNVNOXFILVFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(azidomethyl)quinazolin-4(3H)-one 在 三苯基膦 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 (S)-1-((4-oxo-3H-quinazolin-2-yl)methyl)-3-(1-phenylethyl)urea
  参考文献：
  名称：

  Chemical Probes to Study ADP-Ribosylation: Synthesis and Biochemical Evaluation of Inhibitors of the Human ADP-Ribosyltransferase ARTD3/PARP3

  摘要：

  The racemic 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-[1-(pyridin-2-yl)ethyl]propanamide, 1, has previously been identified as a potent but unselective inhibitor of diphtheria toxin-like ADP-ribosyltransferase 3 (ARTD3). Herein we describe synthesis and evaluation of SS compounds in this class. It was found that the stereochemistry is of great importance for both selectivity and potency and that substituents on the phenyl ring resulted in poor solubility. Certain variations at the meso position were tolerated and caused a large shift in the binding pose. Changes to the ethylene linker that connects the quinazolinone to the amide were also investigated but proved detrimental to binding. By combination of synthetic organic chemistry and structure-based design, two selective inhibitors of ARTD3 were discovered.

  DOI：

  10.1021/jm401394u
• 作为产物：
  描述：

  2-methoxyacetamidobenzonitrile 在 sodium azide 、 四溴化碳 、 氢溴酸 、 过氧化脲素 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 22.33h， 生成 2-(azidomethyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Chemical Probes to Study ADP-Ribosylation: Synthesis and Biochemical Evaluation of Inhibitors of the Human ADP-Ribosyltransferase ARTD3/PARP3

  摘要：

  The racemic 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-[1-(pyridin-2-yl)ethyl]propanamide, 1, has previously been identified as a potent but unselective inhibitor of diphtheria toxin-like ADP-ribosyltransferase 3 (ARTD3). Herein we describe synthesis and evaluation of SS compounds in this class. It was found that the stereochemistry is of great importance for both selectivity and potency and that substituents on the phenyl ring resulted in poor solubility. Certain variations at the meso position were tolerated and caused a large shift in the binding pose. Changes to the ethylene linker that connects the quinazolinone to the amide were also investigated but proved detrimental to binding. By combination of synthetic organic chemistry and structure-based design, two selective inhibitors of ARTD3 were discovered.

  DOI：

  10.1021/jm401394u

文献信息

• 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
• Monomeric, dimeric and tetrameric triazoles which also include nitrones
  作者：Mohamed A. Ameen

  DOI：10.3184/174751917x14944355549140

  日期：2017.6

  The synthesis of some novel nitrones as part of molecules with a potential dual biological functionality is described. Novel aldehydes with 1,2,3-triazole linkers were synthesised and the nitrones were introduced by the classical methodology by reacting the aldehyde with phenyl hydroxylamine.

  本文介绍了一些新型亚硝基化合物的合成，它们是具有潜在双重生物功能的分子的一部分。研究人员合成了带有 1,2,3- 三唑连接物的新型醛，并采用经典方法通过醛与苯基羟胺的反应引入了亚硝基化合物。
• Thermal, non-catalyzed Huisgen cycloaddition for the preparation of 4,5-bis(trimethylsilyl)-1H-1,2,3-triazoles
  作者：Ronald G. Brisbois、Alexandra M. Bergan、Aubrey J. Ellison、Percy Y. Griffin、Kent C. Hackbarth、Steven R. Larson

  DOI：10.1016/j.tetlet.2012.11.019

  日期：2013.1

  The 1,2,3-triazole scaffold is an important pharmacophore and a versatile, increasingly leveraged, sub-structure in biochemical, materials, polymer, and metal-coordinating applications. Continuing advances in 1,2,3-triazole construction, by either non-catalyzed or metal-catalyzed azide/alkyne cycloaddition, foster further creative use. The work reported here establishes a general protocol for the synthesis of 4,5-bis(trimethylsilyl)-1H-1,2,3-triazoles via thermal Huisgen cycloaddition between azides and bis(trimethylsilyl)acetylene. (C) 2012 Elsevier Ltd. All rights reserved.