N-(2-methyl-4-oxoquinazolin-3(4H)-yl)benzamide | 6761-14-4

• 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: N-(2-methyl-4-oxoquinazolin-3(4H)-yl)benzamide
• 英文别名: N-(2-methyl-4-oxoquinazolin-4(3H)-yl)benzamide；3-benzoylamino-2-methyl-3H-quinazolin-4-one；N-(2-methyl-4-oxo-4H-quinazolin-3-yl)-benzamide；N-(2-Methyl-4-oxo-4H-chinazolin-3-yl)-benzamid；N-(2-methyl-4-oxoquinazolin-3-yl)benzamide
• CAS: 6761-14-4
• 化学式: C₁₆H₁₃N₃O₂
• 分子量: 279.298
• InChiKey: JQCDMRJKMBYDBB-UHFFFAOYSA-N

物化性质

• 熔点：
  182-184 °C
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 溶解度：
  40.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-methyl-4-oxoquinazolin-3(4H)-yl)benzamide 在 sodium hydroxide 作用下， 反应 12.0h， 生成 2-(3-methyl-5-phenyl-[1,2,4]triazol-4-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  The chemical simulation of the “atp-imidazole” cycle

  摘要：

  DOI：

  10.1016/s0040-4020(01)87289-6
• 作为产物：
  描述：

  N-(N-acetyl-anthraniloyl)-N'-benzoyl-hydrazine 生成 N-(2-methyl-4-oxoquinazolin-3(4H)-yl)benzamide
  参考文献：
  名称：

  Heller, Journal fur praktische Chemie (Leipzig 1954), 1925, vol. <2> 111, p. 48

  摘要：

  DOI：

文献信息

• An Efficient One-Pot Access to Quinazolinone Derivatives Using TiO2 Nanoparticles as Catalyst: Synthesis and Vasorelaxant Activity Evaluation
  作者：Ali Khalafi-Nezhad、Farhad Panahi、Saghar Haghighi、Azar Purkhosrow

  DOI：10.1055/s-0031-1290610

  日期：2012.4

  A variety of quinazolinone derivatives were successfully synthesized, via a three-component condensation reaction between anthranilic acid, acetic anhydride, and amines. This process was accomplished in the presence of catalytic amount of titanium dioxide nanoparticles (nano-TiO2), under solvent-free conditions. The synthesized compounds were evaluated for their vasorelaxant activity as they revealed a range of activities on the isolated thoracic rat aorta.

  成功合成了一系列奎嗪啉酮衍生物，通过对氨基苯甲酸、醋酸酐和胺类进行三组分缩合反应。在无溶剂条件下，使用催化量的二氧化钛纳米颗粒（nano-TiO2）完成该过程。合成的化合物被评估其血管舒张活性，因为它们在分离的胸部大鼠主动脉上表现出一系列活性。
• Rational design and atroposelective synthesis of N–N axially chiral compounds
  作者：Guang-Jian Mei、Jonathan J. Wong、Wenrui Zheng、Anjanay A. Nangia、K.N. Houk、Yixin Lu

  DOI：10.1016/j.chempr.2021.07.013

  日期：2021.10

  synthesis of N–N axially chiral compounds has been accomplished via a quinidine catalyzed N-allylic alkylation reaction. These N–N axially chiral frameworks are a new addition to the families of axially chiral molecules and to the atropisomerism involving heteroatom(s), e.g., N, O, and S. The reaction takes place smoothly under mild conditions and displays excellent functional group tolerance, allowing

  N-N 轴向手性化合物的第一个催化不对称合成是通过奎尼丁催化的 N-烯丙基烷基化反应完成的。这些 N-N 轴向手性骨架是轴向手性分子家族和涉及杂原子（例如 N、O 和 S）的阻转异构现象的新成员。反应在温和条件下顺利进行，并显示出优异的官能团耐受性，允许以高产率和优异的对映选择性轻松获得各种 N-N 轴向手性 1-氨基吡咯和 3-氨基喹唑啉酮。DFT 计算已用于了解对映选择性的起源，并为设计此类其他分子提供指导。
• Ibrahim, S. S.; Abdel-Halim, A. M.; Gabr, Y., Journal of Chemical Research, Miniprint, 1997, # 5, p. 1041 - 1063
  作者：Ibrahim, S. S.、Abdel-Halim, A. M.、Gabr, Y.、El-Edfawy, S.、Abdel-Rahman, R. M.

  DOI：——

  日期：——
• Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases
  作者：Mahmud Tareq Hassan Khan、Rasool Khan、Yimingjiang Wuxiuer、Mohammad Arfan、Manzoor Ahmed、Ingebrigt Sylte

  DOI：10.1016/j.bmc.2010.04.083

  日期：2010.6.15

  A combinatorial series of novel quinazolin-4(3H)-ones were synthesised and their structures were established based on spectroscopic data (IR, NMR, EI-MS, and FAB-MS). The compounds were tested for inhibition of the zinc metalloproteinase thermolysin (TLN) utilizing a chemical array-based approach. Some of the compounds were found to inhibit TLN, with IC50 values ranging from 0.0115 mu M (compound 3) to 122,637 mu M (compound 29). Compound 3 [3-phenyl-2-(trifluoromethyl) quinazolin-4(3H)-one] (IC50 = 0.0115 mu M) and compound 35 [3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4 (1H)-one] (IC50 = 0.2477 mu M) were found to be the most potent inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.
• The First Authentic Synthesis of the Previously Reported 2-Phenyl-3,4-dihydro-5<i>H</i>-1,3,4-benzotriazepin-5-one
  作者：Norton P. Peet

  DOI：10.1055/s-1984-31083

  日期：——