Acta Pharm. 59 (2009) 365-382

full paper

Original research paper

Synthesis and biological activities of new substituted thiazoline-quinoline derivatives

MOSTAFA A. HUSSEIN, ABDEL-HAMID N. KAFAFY, SAMIA G. ABDEL-MOTY and OLA MOHAMED F. ABOU-GHADIR

mostafa1705@yahoo.com

Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Assiut University, Assiut-71526, Egypt

Accepted July 31, 2009

5-Acyl-8-hydroxyquinoline-2-(3'-substituted-4'-aryl-2,3-dihydrothiazol-2'-ylide- ne)hydrazones, 5a-e to 10a-c, were prepared by the reaction of the appropriate 5-acyl-8-hydroxyquinoline-4-substituted thiosemicarbazones 3a-e and phenacyl bromides 4a-e. Structures of the new compounds were verified on the basis of spectral and elemental analyses. Twenty-eight new compounds were tested for their possible antimicrobial activities. Most of the tested compounds showed weak to moderate antibacterial activity against most of the bacterial strains used in comparison with gatifloxacin as a reference drug. The test compounds showed weak to moderate antifungal activity against tested fungi in comparison with ketoconazole as a reference drug. On the other hand, the newly synthesized compounds were tested for their anti-inflammatory effects and most of them showed good to excellent anti-inflammatory activity compared to indomethacin. Moreover, ulcerogenicity and the median lethal dose (LD₅₀) of the most active anti-inflammatory compounds 6b and 9e were determined in mice; they were non-toxic at doses up to 400 mg kg^-1 after i.p. administration.

Keywords: quinoline, thiosemicarbazone, thiazoline, phenacyl bromide, antimicrobial, anti-inflammatory