Keywords : Citraconamic acids
Synthesis and preliminary evaluation of antimicrobial activity of new sulfonamido and acetamido cyclic imides linked to benzothiazole moiety
karbala journal of pharmaceutical sciences,
Volume 2, Issue 2, Pages 59-80
A new series of citraconimides connected to benzothiazole moiety through sulfonamido group have been prepared by multistep synthesis.In the first step two citraconamic acids N-phenyl and N-benzyl citraconamic acids were prepared via reaction of citraconic anhydride with aniline or benzyl amine. Dehydration of the prepared amic acids by fusion or by treatment with acetic anhydride and anhydrous sodium acetate in the second step afforded N-phenyl and N-benzyl citraconimides which inturn were treated with chloro sulfonic acid in the third step producing 4- ( N-citraconimidyl ) phenyl sulfonyl chloride and 4-(N-citraconimidyl) benzyl sulfonyl chloride respectively. In the fourth step each one of the two prepared sulfonyl chlorides was introduced in reaction with ten substituted -2-amino benzothizoles producing ten N-(4-(substituted benzothiazole-2-yl) sulfon amido phenyl ) citraconimides and ten N-(4-substituted benzothiazole-2-yl)sulfonamido benzyl) citraconimides. Moreover, a series of new phthalimides and succinimides linked to benzothiazole moiety through acetamido group were synthesized via reaction of 2-chloroacetyl amino benzothiazoles with phthalimide and succinimide. Microbiological activities of the prepared imides against four types of bacteria (Staphylococcus aureus , strepto pyogenes , Escherichia coli and pseudomonas aeuroginosa) and candida albicans fungi were evaluated and the results showed that the tested compounds have good antibacterial activity.