Synthesis and biological activities of new substituted thiazoline-quinoline derivatives.
5-Acyl-8-hydroxyquinoline-2-(3'-substituted-4'-aryl-2,3-dihydrothiazol-2'-ylidene)hydrazones, 5a-e to 10a-c, were prepared by the reaction of 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 (LD(50)) 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.
Hussein
Mostafa A
MA
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Assiut University, Assiut-71526, Egypt. mostafa1705@yahoo.com
Kafafy
Abdel-Hamid N
AH
Abdel-Moty
Samia G
SG
Abou-Ghadir
Ola Mohamed F
OM
D000098:Acetophenones / Q000737:chemistry*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000494:pharmacology*; D000935:Antifungal Agents / Q000494:pharmacology*; D004487:Edema / Q000139:chemically induced; D024841:Fluoroquinolones / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D000077734:Gatifloxacin; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D007213:Indomethacin / Q000494:pharmacology; D007654:Ketoconazole / Q000494:pharmacology; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D013276:Stomach Ulcer / Q000139:chemically induced; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D023382:Toxicity Tests, Acute
D000098:Acetophenones; D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000935:Antifungal Agents; D024841:Fluoroquinolones; D011804:Quinolines; D013844:Thiazoles; C013190:phenacyl bromide; D000077734:Gatifloxacin; D007654:Ketoconazole; D007213:Indomethacin