Synthesis and antiinflammatory screening of some quinazoline and quinazolyl-4-oxoquinazoline derivatives.
Synthesis of some new derivatives of 2-aryl-4-oxo-1-(4-quinazolyl)quinazolines is described. Methyl N-(4-quinazolyl)anthranilate was allowed to react with phenyl iso(thio)cyanate to give 3-phenyl-1-(4-quinazolyl)-1, 2, 3, 4-tetrahydro-2, 4-dioxo- and 4-oxo-2-thioxoquinazolines (3a and 3b respectively) Alternatively, anthranilic acid amide derivatives were subjected to cyclization with aromatic aldehydes to give 2-aryl-4-oxo-1-(4-quinazolyl)-1, 2, 3, 4-tetrahydroquinazolines 5. On the other hand, 2-chloro-4-(4-substituted 1-piperazinyl)quinazoline derivatives were subjected to the same type of reactions at the 2-position to afford the corresponding quinazoline derivatives 8 and 10 respectively. Furthermore, the acid amide 4b cyclized with acid chlorides to give the corresponding 2-aryl-1-(2-chloro-4-quinazolyl)-4-oxo-1, 4-dihydroquinazolines 11 from which the triazoloquinazoline derivatives 13 and 15 were synthesized through the intermediate hydrazine derivatives 12. Most of the newly synthesized compounds were tested for their antiinflammatory activities. However, some of the novel compounds were found to exhibit good antiinflammatory potencies.
Gineinah
Magdy M
MM
Pharmaceutical Organic Chemistry, College of Pharmacy, Mansoura University, Mansoura 35516, Egypt. maggineinah@yahoo.com
El-Sherbeny
Magda A
MA
Nasr
Magda N
MN
Maarouf
Azza R
AR
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008297:Male; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
D000894:Anti-Inflammatory Agents, Non-Steroidal; D011799:Quinazolines