Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus

Authors : Muhammet ÖZYANIK, Serpil DEMİRCİ, Hakan BEKTAŞ, Neslihan DEMİRBAŞ

Pages : 233-246

Doi:10.3906/sag-1302-47

View : 14 | Download : 5

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Quinoline-2-carbohydrazide insert ignore into journalissuearticles values(2); obtained from quinaldic acid insert ignore into journalissuearticles values(1); was converted to the corresponding carbothioamide 3 and carboxamide 6 by treatment with benzylisoinsert ignore into journalissuearticles values(thio);cyanate. The basic treatment of 3 and 6 yielded the corresponding 1,2,4-triazole derivatives 4 and 7. The synthesis of 5-insert ignore into journalissuearticles values(quinolin-2-yl);-1,3,4- oxadiazol-2-thiol insert ignore into journalissuearticles values(9); was performed from the reaction of 1 with CS2 in basic media. The Mannich reaction of compounds 4, 7, and 9 resulted in the formation of aminoalkylated derivatives 5a-c, 8, and 10a,b. The condensation of 1 with thiosemicarbazide, carbohydrazide, or thiocarbohydrazide gave the corresponding 1,2,4-triazole derivatives insert ignore into journalissuearticles values(11-13);. The treatment of 4-amino-5-insert ignore into journalissuearticles values(quinolin-2-yl);- 4H-1,2,4-triazole-3-thiol insert ignore into journalissuearticles values(13); with 4-chlorophenacyl bromide caused the formation of fused triazolothiadiazine 14. The condensation of 13 with 4-methoxybenzaldehyde generated the corresponding Schiff base 15. The newly synthesized compounds were characterized by elemental analyses, IR, 1H-NMR, 13C-NMR, and mass spectra. The antimicrobial activity study revealed that some of the newly synthesized compounds showed good to moderate activity against a variety of microorganisms.
Keywords : Quinoline, 1, 3, 4 thiadiazole, 1, 2, 4 triazole, Mannich base, antimicrobial activity