Synthesis of some 5-azo(4'-substituted benzene-sulphamoyl)-8-hydroxyquinolines with antidotal and antibacterial activities.

Abstract

5-Azo(4'-substituted benzenesulphamoyl)-8-hydroxyquinolines(III) have been prepared by coupling of the appropriate p-substituted benzenesulphamoyldiazonium acetates with 8-hydroxyquinoline. The corresponding copper chelates(IV) and iron chelates(V) were also prepared in a 1:2 metal to ligand ratio. Structures of III, IV and V were confirmed by some representative UV, IR, and NMR spectrometry in addition to microanalysis. Antidotal activity of four ligands (IIIa, IIId, IIIf, and IIIi) has been evaluated in mice against the toxicity of lead acetate and copper sulphate. Study revealed that compound IIIf elicited significant antidotal activity against lead and copper poisoning, while IIIi was potent only against lead poisoning. Antibacterial activity of compounds III, IV, and V was also determined in comparison to sulphanilamide against Staph. aureus, Bacill. cereus, and Esch. coli. The test compounds showed variable bacteriostatic activities, and some of them (IIIc, IIId, IIIf, Ve, IIIg, and Vi) are more effective than the reference drug, especially against Bacill. cereus.