ABSTRACT
Given the significant low yield (19-43%) in reported results on the cyclocondensation of sulfaguanidine acetate with chalcones, a careful reinvestigation was carried out. A new series of chalcones, bearing electron-attracting groups in the aromatic moiety, have been used as precursors in the synthesis of diphenylsulfapyrimidine acetates with good yield. All synthesized compounds were active against G(+)- and G(-)-bacteria, and fungi. Combination of substituents (Cl, OMe, NO2, etc.) enhanced antimicrobial activity. Derivative with two NO2 groups exhibits an activity comparable with sulfadiazine.
Subject(s)
Anti-Infective Agents/chemical synthesis , Chalcone/chemistry , Pyrimidines/chemical synthesis , Sulfonamides/chemical synthesis , Acetates/chemical synthesis , Acetates/chemistry , Acetates/pharmacology , Anti-Bacterial Agents , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Fungi/drug effects , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Microbial Sensitivity Tests , Pyrimidines/chemistry , Pyrimidines/pharmacology , Structure-Activity Relationship , Sulfaguanidine/chemistry , Sulfonamides/chemistry , Sulfonamides/pharmacologyABSTRACT
3-(1,1-Dioxadibenzothien-4-oyl)acrylic acid (1) was condensed with compounds containing active methylene groups under Michael reaction conditions to furnish the Michael adducts (lactones 2a-c, lactams 3a-c, ketones 4a,b). The behavior of these adducts toward the action of hydrazine hydrate were investigated. The compounds were tested for their biological properties.
