2-methyl-4-oxo-3-o-tolyl-3,4-dihydroquinazolin-8-yl acetate | 1319735-56-2

• 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-methyl-4-oxo-3-o-tolyl-3,4-dihydroquinazolin-8-yl acetate
• 英文别名: 8-acetyloxy-2-methyl-3-(2-methylphenyl)-4(3H)-quinazolinone；[2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yl] acetate
• CAS: 1319735-56-2
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: HLLIJIUYOWQFSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-4-oxo-3-o-tolyl-3,4-dihydroquinazolin-8-yl acetate 在 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 20.0h， 生成 [2-methyl-3-(2-methylphenyl)-4(3H)-quinazolinon-8-yloxy]acetohydrazide
  参考文献：
  名称：

  Synthesis and anticonvulsant evaluation of some novel 4(3H)-quinazolinones

  摘要：

  A series of novel quinazoline derivatives, methaqualone analogs, were synthesized, evaluated for their anticonvulsant activity against electrically and chemically (pentylenetetrazole, picrotoxin, and strychnine) induced seizures and compared with the standard drugs methaqualone and sodium valproate. 3,4-Dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yl propanoate, benzenesulfonate, and 4-nitrobenzenesulfonate as well as 2-methyl-3-(2-methylphenyl)-8-methoxy-4(3H)-quinazolinone and 2-[3,4-dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yloxy]acetic acid hydrazide were found to be the most potent compounds of this series accompanied with relatively low neurotoxicity and low toxicity in the median lethal dose test as compared with the reference drugs.

  DOI：

  10.1007/s00706-011-0525-3
• 作为产物：
  描述：

  3-羟基-2-氨基苯甲酸 以 吡啶 为溶剂， 反应 11.0h， 生成 2-methyl-4-oxo-3-o-tolyl-3,4-dihydroquinazolin-8-yl acetate
  参考文献：
  名称：

  Synthesis and anticonvulsant evaluation of some novel 4(3H)-quinazolinones

  摘要：

  A series of novel quinazoline derivatives, methaqualone analogs, were synthesized, evaluated for their anticonvulsant activity against electrically and chemically (pentylenetetrazole, picrotoxin, and strychnine) induced seizures and compared with the standard drugs methaqualone and sodium valproate. 3,4-Dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yl propanoate, benzenesulfonate, and 4-nitrobenzenesulfonate as well as 2-methyl-3-(2-methylphenyl)-8-methoxy-4(3H)-quinazolinone and 2-[3,4-dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yloxy]acetic acid hydrazide were found to be the most potent compounds of this series accompanied with relatively low neurotoxicity and low toxicity in the median lethal dose test as compared with the reference drugs.

  DOI：

  10.1007/s00706-011-0525-3

文献信息

• Design and evaluation of new hybrid pharmacophore quinazolino-tetrazoles as anticonvulsant strategy
  作者：Sachin Malik、Suroor A. Khan

  DOI：10.1007/s00044-013-0630-4

  日期：2014.1

  The anticonvulsant study of 25 newly synthesized quinazolin-4(3H)-one substituted 1H and 2H-tetrazoles (6a–6d, 7a–7b, 8a–8i, 8a′–8i′) was executed. The study employing the maximal electroshock and subcutaneous pentylenetetrazole (scPTZ) screens, the ‘gold standards’ in the preliminary anticonvulsant breakthrough and the neurotoxicity study applying the rotorod test unveiled a triad of compounds 6c

  进行了25种新合成的喹唑啉-4（3 H）-一取代的1 H和2 H-四唑（6a - 6d，7a - 7b，8a - 8i，8a' - 8i '）的抗惊厥研究。这项研究采用了最大的电击和皮下戊四氮（scPTZ）筛查，抗惊厥的初步突破中的“金标准”以及应用旋翼仪测试的神经毒性研究，揭示了化合物6c，7b和8i的三元组作为合成化合物纲要中的隐约内容。在大鼠口服给药后，这些化合物的定量数据显示7b证明了MES筛查中的显着位置，scPTZ中的保护性指数（PI）分别> 39.67和6c，分别表示PI> 3.10。所有有效的化合物都没有毒性。
• Synthesis and anticonvulsant evaluation of some novel 4(3H)-quinazolinones
  作者：Adel S. El-Azab、Kamal E. H. ElTahir、Sabry M. Attia

  DOI：10.1007/s00706-011-0525-3

  日期：2011.8

  A series of novel quinazoline derivatives, methaqualone analogs, were synthesized, evaluated for their anticonvulsant activity against electrically and chemically (pentylenetetrazole, picrotoxin, and strychnine) induced seizures and compared with the standard drugs methaqualone and sodium valproate. 3,4-Dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yl propanoate, benzenesulfonate, and 4-nitrobenzenesulfonate as well as 2-methyl-3-(2-methylphenyl)-8-methoxy-4(3H)-quinazolinone and 2-[3,4-dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yloxy]acetic acid hydrazide were found to be the most potent compounds of this series accompanied with relatively low neurotoxicity and low toxicity in the median lethal dose test as compared with the reference drugs.