3-(3-aminoethyl)-2-(4-methylphenyl)quinazolin-4(3H)-one | 1236769-21-3

• 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: 3-(3-aminoethyl)-2-(4-methylphenyl)quinazolin-4(3H)-one
• 英文别名: 3-(2-aminoethyl)-2-p-tolyl-3H-quinazolin-4-one；3-(2-Aminoethyl)-2-(4-methylphenyl)quinazolin-4-one
• CAS: 1236769-21-3
• 化学式: C₁₇H₁₇N₃O
• 分子量: 279.341
• InChiKey: DWSVWJMXZVJCIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-methylphenyl)-4H-3,1-benzoxazin-4-one 、 乙二胺 以 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到3-(3-aminoethyl)-2-(4-methylphenyl)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

• QUINAZOLINONES
  申请人：MERCK PATENT GmbH

  公开号：EP1216235A1

  公开（公告）日：2002-06-26
• US6890930B1
  申请人：——

  公开号：US6890930B1

  公开（公告）日：2005-05-10
• [EN] QUINAZOLINONES<br/>[FR] QUINAZOLINONES
  申请人：MERCK PATENT GMBH

  公开号：WO2001023365A1

  公开（公告）日：2001-04-05

  Quinazolinones of formula (I) in which R, R?1, R2, R3, R4¿, Y, Z, n and m have the meaning indicated in Patent Claim 1, and their salts or solvates as glycoprotein IbIX antagonists.
• 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.