2-(4-methylphenyl)-3-(1,3-thiazol-2-yl)quinazolin-4(3H)-one | 330829-03-3

• 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-(4-methylphenyl)-3-(1,3-thiazol-2-yl)quinazolin-4(3H)-one
• 英文别名: 2-(4-methylphenyl)-3-(1,3-thiazol-2-yl)quinazolin-4-one
• CAS: 330829-03-3
• 化学式: C₁₈H₁₃N₃OS
• 分子量: 319.387
• InChiKey: OFOCYFHKXGXVAH-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C(Solv: ethanol (64-17-5))
• 沸点：
  543.3±43.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基噻唑 、 2-(4-methylphenyl)-4H-3,1-benzoxazin-4-one 在 吡啶 作用下， 反应 10.0h， 以78.3%的产率得到2-(4-methylphenyl)-3-(1,3-thiazol-2-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.04.083

文献信息

• 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.