NOVEL 6,8-DIBROMO-4(3H)-QUINAZOLINONE DERIVATIVES OF PROMISING ANTI-INFLAMMATORY AND ANALGESIC PROPERTIES

作者：Mosaad Mohamed S^*; Mohsen Kamel M; Emad Kassem M M; Abotaleb Nageh; Salwa Nofal M; Marwa Ahmed F

来源：Acta Poloniae Pharmaceutica, 2010, 67(2): 159-171.

• 6.8-dibromo-2-phenylbenzoxazin-4-one
• 6,8-dibromo-2-phenyl-quinazolin-4-one
• pyridine-2(1H)-ones
• 2-iminopyridines
• 2-aminopyrans
• 1,3-propen-1-ones
• pyrazolines
• pyrimidinones
• pyrimidine-thiones
• anti-inflammatory and analgesic activities

A new series of the title compounds incorporated into diverse N and O heterocyclic moieties of pharmacoavailability as anti-inflammatory and analgesic agents, were synthesized starting with 6.8-dibromo-2-phenyl-4H-3,1-benzoxazin-4-one (I) by its fusion with p-aminoacetophenone to give the new intermediate compound, 6,8-dibromo-2-phenyl-3-(4-acetylphenyl)-4(3H)-quinazolinone (II). The one pot reaction of II with the appropriate aromatic aldehydes and anhyd. ammonium acetate in the presence of either ethyl cyanoacetate or malononitrile afforded the corresponding 2(1H)-pyridones III or 2(1H)-iminopyridines IV, respectively. while its reaction with malononitrile and aromatic aldehydes ill piperidine gave 2-aminopyrans V. Also, reaction of the acetyl derivative II with aromatic aldehydes at afforded the corresponding 1,3-propen-1-one derivatives VI which underwent cyclization with hydrazine to give the corresponding pyrazolines VII and with urea and/or thiourea to give the corresponding tetrahydropyrimidin-2-ones and/or tetrahydropyrimidin-2-thiones VIII. Some representative examples of the new compounds showed promising anti-inflammatory and analgesic activities in experimental animals.

• 出版日期2010-4