ABSTRACT
Novel azo-dyes have been synthesized by diazotization of 4-amino benzene-4'-(substituted heterocyclo) sulphonamide derivatives and coupling with 1-oxa-4-thia-spiro[4,4]nonan-2-one (I) and/or with 1-oxa-4-thia- spiro[4,5]decan-2-one (I') in acid medium to give the corresponding 3-azo-(4'-substituted benzenesulphonamido)-1-oxa-4-thia-spiro[4,4]nonan-2-one (II-IX) and/or 1-oxa-4-thia-spiro[4,5]decan-2-one (II'-IX'] as spiro-ligands. Treatment of these ligands with metal salts of iron (Fe3+), copper (Cu2+) and mercury (Hg2+) as chlorides in ethanolic solution furnished the corresponding metal chelates (IIa-c-IXa-c) and/or (II'a-c-IX'a-c). The compounds were tested in vitro for antimicrobial activity to study the structure-activity relationship.
Subject(s)
Azo Compounds/chemical synthesis , Spiro Compounds/chemical synthesis , Sulfonamides/chemical synthesis , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Azo Compounds/chemistry , Azo Compounds/pharmacology , Bacteria/drug effects , Biotechnology , Fungi/drug effects , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Spectrophotometry, Infrared , Spiro Compounds/chemistry , Spiro Compounds/pharmacology , Structure-Activity Relationship , Sulfonamides/chemistry , Sulfonamides/pharmacologyABSTRACT
4-Hydroxyacetophenone (1) was reacted with cinnamonitrile derivatives (2-6) to give 3-cyano-4-(substituted phenyl)-6-(p-hydroxyphenyl)-pyridines (7-11). Interaction of compounds 7-9 with 4'-substituted heterocyclo-benzenesulphonyl diazonium chloride gave the corresponding 3-cyano-4-(substituted phenyl)-6-(3'-azobenzene sulphonamido-4'-hydroxyphenyl) pyridines (12-29). The corresponding iron (III) copper (II) and mercury (II) chelates were also prepared in a 1:2 metal-to-ligand ratio. All the synthesized compounds were characterized on the basis of microanalysis, IR and 1H-NMR spectrometry.
Subject(s)
Sulfonamides/chemical synthesis , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Azo Compounds/chemical synthesis , Azo Compounds/chemistry , Azo Compounds/pharmacology , Bacteria/drug effects , Biotechnology , Coloring Agents/chemical synthesis , Coloring Agents/chemistry , Coloring Agents/pharmacology , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Nitriles/chemical synthesis , Nitriles/chemistry , Nitriles/pharmacology , Pyridines/chemical synthesis , Pyridines/chemistry , Pyridines/pharmacology , Spectrophotometry, Infrared , Structure-Activity Relationship , Sulfonamides/chemistry , Sulfonamides/pharmacologyABSTRACT
Interaction of (3-aryloxymethyl-4-phenyl-s-triazol-5-yl)thioacethydrazid e (1a-c) with phenyl isocyanate and/or with methyl/phenyl isothiocyanate gave semicarbazides (2a-c) and thiosemicarbazides (3a-f) respectively. Cyclization of (3a-f) yielded s-triazoles (4a-f). Compounds 4b,d,f were easily alkylated giving S-substituted thio-s-triazoles (5a-e). Furthermore, compounds 4b,d,f underwent a Mannich reaction to give the expected Mannich bases (6a-f). All compounds were fully confirmed by elemental and spectral analyses and have been screened in vitro for antimicrobial activity.
Subject(s)
Triazoles/chemical synthesis , Anti-Bacterial Agents , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Bacteria/drug effects , Biotechnology , Fungi/drug effects , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Structure-Activity Relationship , Triazoles/chemistry , Triazoles/pharmacologyABSTRACT
Some novel azo-Sulpha drugs as 3-methyl-N-azo-(4'-substituted heterocyclo-benzene-sulphamoyl) quinoxaline-2-ones (1-11) and 3-methyl-N-azo-(4'-substituted heterocyclo-benzene-sulphamoyl)-quinoxaline-2-thiones (1'-11') were synthesized by coupling 4'-substituted heterocyclo-benzene-sulphamoyl diazonium acetates with 3-methyl-N-(1H)-quinoxaline-2-one and/or with 3-methyl-N(1H) quinoxaline-2-thione in acid medium. The corresponding iron (III) (1a-11, 1'a-11'a) copper (II) (1b-1b'-7b') and mercury (II) (1c-11c, 1c'-11c) chelates were also prepared in a 1:1 metal-to-ligand ratio. The ligands and their chelates were characterized on the basis of microanalysis, UV, IR and H'-NMR spectrometry, and were tested in vitro for their antibacterial and antifungal activities.
Subject(s)
Anti-Infective Agents/chemical synthesis , Quinoxalines/chemical synthesis , Sulfonamides/chemical synthesis , Azo Compounds/chemical synthesis , Chelating Agents/chemical synthesis , Microbial Sensitivity TestsABSTRACT
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.
