Nucleophilic ring opening of 1,4-disubstituted 2-pyrrolidones with hydrazine. Synthesis of azoles with a high antibacterial activity

Abstract

3-(1H-Benzimidazol-2-yl)-4-[(phenyl and 4-substituted phenyl)amino]butanohydrazides were synthesized in good yields by treating the corresponding 4-(1H-benzimidazol-2-yl)-1-phenyl(substituted phenyl)-2-pyrrolidinones with the excess of hydrazine monohydrate. The utility of the newly synthesized hydrazides in the preparation of pyrroles, pyrazoles, oxadiazoles and triazoles has been demonstrated. All compounds were screened for their antibacterial activity. A significant antibacterial activity was found.

Beta and Gamma Amino Acid-Substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases

“…Pyrrolidinones 1a,b, which were used in this work as precursors, were synthesized according to the methods described in previous works [29,30]. Compounds 4-((2-(hydrazinecarbonyl)-4hydrazineyl-4-oxobutyl)amino)benzenesulfonamide (2a) and 3-chloro-4-((2-(hydrazinecarbonyl)-4-hydrazineyl-4-oxobutyl)amino)benzenesulfonamide (2b) were synthesized by nucleophilic ring-opening reactions of pyrrolidones 1a,b by heating them under reflux in an excess of hydrazine monohydrate [32] (Scheme 1). The structures of 2a,b and all of the other compounds have been confirmed by FT-IR, 1 H and 13 C NMR spectroscopy, and mass spectrometry or elemental analysis data.…”

“…Compound 25b also had an unusually strong interaction with CAIII (K d_obs 5000 nM, Table 2), despite having large substituents, which usually contribute to steric hindrance and weak binding to CAIII. (27)(28)(29)(30)(31)(32)(33)(34)(35)(36) Binding to CA Compounds 27-6 had greater asymmetry than compounds 2-25a,b (Figure 3). Compounds 27-34 and 36 were tested with all catalytically active CA isozymes.…”

Synthesis, Characterization and Bioassay of Novel Substituted 1-(3-(1,3-Thiazol-2-yl)phenyl)-5-oxopyrrolidines

“…For more extensive analysis of biological properties of the compounds resynthesized benzimidazole 22 [49] was alkylated with iodoethane at solvent-free conditions and in the presence of potassium hydroxide and sodium carbonate. and Salmonella enterica enteritidis (ATCC 13076) bacteria for their in vitro antibacterial activity by broth dilution and spread-plate techniques [50][51][52]. Oxytetracycline was used as a control (C) for antibacterial activity screening.…”