Novel 6,8-dibromo-4(3H)-quinazolinone derivatives of promising anti-inflammatory and analgesic properties.
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 in piperidine gave 2-aminopyrans V. Also, reaction of the acetyl derivative II with aromatic aldehydes 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.
Mosaad
Mohamed S
MS
Faculty of Pharmacy, Helwan University and National Research Centre, Dokki Cairo, Egypt. doctormosaad@hotmail.comtmail.com
Mohsen
Kamel M
KM
Emad
Kassem M M
KM
Abotaleb
Nageh
N
Salwa
Nofal M
NM
Marwa
Ahmed F
AF
D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D008297:Male; D051379:Mice; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D051381:Rats; D013274:Stomach Neoplasms / Q000139:chemically induced*
D000700:Analgesics; D000893:Anti-Inflammatory Agents; D052999:Quinazolinones