Synthesis of some thiazolyl and thiadiazolyl derivatives of 4(3H)-quinazolinone as anti-inflammatory-antimicrobial agents.
This paper describes the synthesis of four series of 4(3H)-quinazolinone derivatives. The first series was prepared by cyclization of the intermediate 3-aryl-2-substituted thiocarbamoylhydrazonomethyl-4(3H)-quinazolinones 2a,b with ethyl bromoacetate to afford the corresponding thiazolidinonyl derivatives 3a,b. The second series were prepared by the cyclization of the intermediate 2a,b with phenacyl bromide or 4-substituted phenacyl bromide giving rise to thiazolinyl derivatives 4a-f. Furthermore, the thiazolidinonyl derivatives 5a,b were obtained by reaction of the intermediate 2a,b with thioglycolic acid. On the other hand, heating the intermediate 2a,b with acetic anhydride afforded the corresponding thiadiazolinyl derivatives 6a,b. Some of the synthesized compounds showed promising anti-inflammatory-antimicrobial activities.
Bekhit
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AA
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, Alexandria, Egypt.
Habib
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NS
Park
Ji Young
JY
D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D007202:Indicators and Reagents; D008826:Microbial Sensitivity Tests; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D051381:Rats; D013276:Stomach Ulcer / Q000139:chemically induced; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity
D000890:Anti-Infective Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D007202:Indicators and Reagents; D011799:Quinazolines; D013844:Thiazoles