3-{[(1E)-(2-hydroxynaphthalen-1-yl)methylene]amino}-2-phenylquinazolin-4(3H)-one | 1236769-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-{[(1E)-(2-hydroxynaphthalen-1-yl)methylene]amino}-2-phenylquinazolin-4(3H)-one
• CAS: 1236769-27-9
• 化学式: C₂₅H₁₇N₃O₂
• 分子量: 391.429
• InChiKey: CDQJXXVDCZDDEY-WGOQTCKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.48
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-氨基-2-苯基-4(3H)-喹唑啉酮 、 2-羟基-1-萘甲醛 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以77.65%的产率得到3-{[(1E)-(2-hydroxynaphthalen-1-yl)methylene]amino}-2-phenylquinazolin-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