3-(2-氨基苯基)-2-甲基喹唑啉-4-酮 | 1789-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-(2-氨基苯基)-2-甲基喹唑啉-4-酮
• 英文名称: 3-(2-aminophenyl)-2-methylquinazolin-4(3H)-one
• 英文别名: 3-(2-amino-phenyl)-2-methyl-3H-quinazolin-4-one；4(3H)-Quinazolinone, 3-(o-aminophenyl)-2-methyl-；3-(2-aminophenyl)-2-methylquinazolin-4-one
• CAS: 1789-01-1
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: KNJPCPIZTHFKDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Trithio-meta-phosphorsaeure-phenylester 、 3-(2-氨基苯基)-2-甲基喹唑啉-4-酮 以 甲苯 为溶剂， 以60%的产率得到O-(3-(2-aminophenyl)-2-methyl-4-((2-(2-methyl-4-thioxoquinazolin-3(4H)-yl) phenyl)amino)-3,4-dihydroquinazolin-4-yl) S-phenyl S-hydrogenphosphorotrithioate
  参考文献：
  名称：

  Synthesis and Antimicrobial Evaluation of New 2-Methylquinazolin-4(3H)-one Phosphorothioates

  摘要：

  A SERIES of new compounds characterized by presence of quinazoline scaffold and phosphorothioate moiety in their molecular structure, was prepared through reacting Japanese reagent (JR, 1a) and Lawesson reagent (LR, 1b) with quinazoline-4-ones (3a-e) in boiling toluene. The expected quinazoline-4-thiones were also formed and well identified. Molecular docking studies were performed to determine the molecular affinity between the new products and the target protein. The starting quinazolines and ten of the new products were in vitro evaluated as antimicrobial agents using Cephradine and Fluconazole as reference drugs for antibacterial and antifungal assays, respectively. Of particularly, the dioxathiaphosphinane (12) and benzoxaphospholylidene (17) exhibited 15% potent inhibition that equals to Cephradine against Escherichia coli strains.

  DOI：

  10.21608/ejchem.2019.11548.1736
• 作为产物：
  描述：

  邻氨基苯甲酸 以 乙醇 为溶剂， 反应 12.16h， 生成 3-(2-氨基苯基)-2-甲基喹唑啉-4-酮
  参考文献：
  名称：

  Expeditious Synthesis and Spectroscopic Characterization of 2-Methyl-3-substituted-quinazolin-4(3H)-one Derivatives

  摘要：

  喹唉及其衍生物是一类因其治疗多样性和在药物设计和制药中的广泛应用而著名的生物活性杂环化合物。本研究通过将邻氨基苯甲酸转化为2-甲基-4H-3,1-苯并恶嗪-4-酮7，进而与一系列含有氨基的基团反应，合成了一系列2-甲基-3-取代喹唑啉-4(3H)-酮衍生物8a-q。通过选择溶剂和反应温度作为关键参数的精细反应优化研究，实现了无催化剂的合成路线。合成的化合物的化学结构通过IR、UV、1H-NMR、13C-NMR、DEPT-135以及分析数据进行了确认。

  DOI：

  10.13005/ojc/330203

文献信息

• Ruthenium(II) complexes with 2-methyl-3-substituted (3H)-quinazolin-4-ones
  作者：K.Laxma Reddy、P. Lingaiah、K.Veera Reddy

  DOI：10.1016/s0277-5387(00)84550-7

  日期：1986.1

  complexes of some polydentate ON, OO and ONO donors in the form of 2-methyl-3-substituted (3H)-quinazolin-4-ones have been synthesized and studied. The reaction between RuCl2(DMSO)4 and the uninegative bidentate ligands yielded complexes of the type Ru(DMSO)2(OO)2 (OO = MHQ, PHQ, MHEQ, MHPQ or MCMQ), displacing only two DMSO groups along with chlorides, whereas the neutral bidentate ligands gave

  合成了一些多齿ON，OO和ONO供体的钌（II）配合物，它们以2-甲基-3-取代的（3 H）-喹唑啉-4-酮的形式存在，并且研究过。RuCl 2（DMSO）4与非负二齿配体之间的反应产生Ru（DMSO）2（OO）2类型的配合物（OO= MHQ，PHQ，MHEQ，MHPQ或MCMQ），仅取代了两个DMSO基团以及氯化物，而中性双齿配体给出RuCl 2（ON）2（ON= MAQ，PAQ，MANQ，PANQ，MAAQ，MAPQ，MPQ或PPQ），取代了所有DMSO基团。然而，具有O = N = O供体的单负性齿状配体（MHAQ）生成了钌（II）的双螯合物。
• Dash, B.; Dora, E. K.; Panda, C. S., Journal of the Indian Chemical Society, 1980, vol. 57, # 8, p. 835 - 836
  作者：Dash, B.、Dora, E. K.、Panda, C. S.

  DOI：——

  日期：——
• DASH B.; DORA E. K.; PANDA C. S., J. INDIAN CHEM. SOC., 1980, 57, NO 8, 835-836
  作者：DASH B.、 DORA E. K.、 PANDA C. S.

  DOI：——

  日期：——
• Expeditious Synthesis and Spectroscopic Characterization of 2-Methyl-3-substituted-quinazolin-4(3H)-one Derivatives
  作者：OLAYINKA O. AJANI、OLUWATOSIN Y. AUDU、MARKUS W. GERMANN、BABATUNDE L. BELLO

  DOI：10.13005/ojc/330203

  日期：2017.4.28

  Quinazoline and quinazolinone derivatives are well-known bioactive heterocycles owing to their therapeutic diversity and extensive medicinal application in drug design and pharmaceutics. A series of 2-methyl-3-substituted quinazolin-4(3H)-one derivatives 8a-q was herein synthesized from synthetic conversion of anthranilic acid to 2-methyl-4H-3,1-benzoxazi-4-one, 7 which was subsequently transformed to the targeted 2,3-disubstituted quinazolin-4(3H)-one derivatives 8a-q by reacting with some notable amino-containing moieties via an ameliorable pathway. The catalyst-free synthesis was successful achieved by careful reaction optimization study using solvent choice and reaction temperature variability as key parameters. The chemical structures of the synthesized compounds were confirmed by IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as analytical data.

  喹唉及其衍生物是一类因其治疗多样性和在药物设计和制药中的广泛应用而著名的生物活性杂环化合物。本研究通过将邻氨基苯甲酸转化为2-甲基-4H-3,1-苯并恶嗪-4-酮7，进而与一系列含有氨基的基团反应，合成了一系列2-甲基-3-取代喹唑啉-4(3H)-酮衍生物8a-q。通过选择溶剂和反应温度作为关键参数的精细反应优化研究，实现了无催化剂的合成路线。合成的化合物的化学结构通过IR、UV、1H-NMR、13C-NMR、DEPT-135以及分析数据进行了确认。
• Synthesis and Antimicrobial Evaluation of New 2-Methylquinazolin-4(3H)-one Phosphorothioates
  作者：Mona Arsanious、Shaban Darwish、Maysa Mohram、Mahmoud Dondeti.

  DOI：10.21608/ejchem.2019.11548.1736

  日期：2019.4.28

  A SERIES of new compounds characterized by presence of quinazoline scaffold and phosphorothioate moiety in their molecular structure, was prepared through reacting Japanese reagent (JR, 1a) and Lawesson reagent (LR, 1b) with quinazoline-4-ones (3a-e) in boiling toluene. The expected quinazoline-4-thiones were also formed and well identified. Molecular docking studies were performed to determine the molecular affinity between the new products and the target protein. The starting quinazolines and ten of the new products were in vitro evaluated as antimicrobial agents using Cephradine and Fluconazole as reference drugs for antibacterial and antifungal assays, respectively. Of particularly, the dioxathiaphosphinane (12) and benzoxaphospholylidene (17) exhibited 15% potent inhibition that equals to Cephradine against Escherichia coli strains.