Synthesis of sulfonamides bearing 1,3,5-triarylpyrazoline and 4-thiazolidinone moieties as novel antimicrobial agents

Two series of sulfonamides were synthesized from 4-hydrazinylbenzenesulfonamide as the key starting material. 1,3,5-Triarylpyrazoline sulfonamides (2a?i) were obtained by cyclocondensation of various chalcones in 53? ?64 % yields, while 4-thiazolidinone derivatives (4a?e) were synthesized by cycloco...

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Published inJournal of the Serbian Chemical Society Vol. 85; no. 2; pp. 155 - 162
Main Authors Thach, Thi-Dan, Le, Thi, Nguyen, Thien-Annguyen, Dang, Chi-Hien, Dang, Van-Su, Nguyen, Thanh-Danh
Format Journal Article
LanguageEnglish
Published Serbian Chemical Society 2020
Subjects
antimicrobial agents
pyrazoline
sulfonamide
synthesis
thiazolidinone
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Summary:Two series of sulfonamides were synthesized from 4-hydrazinylbenzenesulfonamide as the key starting material. 1,3,5-Triarylpyrazoline sulfonamides (2a?i) were obtained by cyclocondensation of various chalcones in 53? ?64 % yields, while 4-thiazolidinone derivatives (4a?e) were synthesized by cyclocondensation between mercaptoacetic acid and different phenylhydrazones in 43?62 % yields. The synthesized compounds were characterized based on FTIR, 1H-NMR, 13C-NMR and HRMS data. The sulfonamides were evaluated for their in vitro antimicrobial activities against four bacterial strains (E. coli, P. aeruginosa, B. subtillis and S aureus), two filamentous fungal strains (A. niger and F. oxysporum) and two yeast strains (C. albicans and S. cerevisiae). Seven pyrazolines, 2a?c and 2e?h, exhibited significant inhibition of different microbial strains. Among them, compound 2b displayed good antifungal activity against A. niger (MIC value at 12.5 ?g mL-1) over the reference drug. nema
ISSN:0352-5139
1820-7421
DOI:10.2298/JSC180621057T