Biopolym. Cell. 2020; 36(5):381-391.
Bioorganic Chemistry
Synthesis of indoline-thiazolidinone hybrids with antibacterial and antifungal activities
1Konechnyi Y. T., 1Lozynskyi A. V., 1Horishny V. Ya., 2Konechna R. T., 3Vynnytska R. B., 1Korniychuk O. P., 1, 4Lesyk R. B.
  1. Danylo Halytsky Lviv National Medical University
    69, Pekarska Str., Lviv, Ukraine, 79010
  2. Lviv Polytechnic National University
    12, S. Bandery Str., Lviv, Ukraine, 79013
  3. Ivano-Frankivsk National Medical Universitу
    2, Halytska Str., Ivano-Frankivsk, Ukraine, 76018
  4. University of Information Technology and Management in Rzeszow
    2, Sucharskiego Str., Rzeszow, Poland, 35-225

Abstract

Aim. Based of the Knoevenagel condensation reaction the synthesis of new rhodanine-indoline hybrid molecules for screening antibacterial and antifungal activities was accomplished. Methods. Organic synthesis, NMR spectroscopy, pharmacological screening. Results. The reaction between rhodanine-3-propanoic/ethanesulfonic acids and indolecarbaldehydes in the acetic acid medium providing series of 5-indolylmethylenerhodanine-3-carboxylic/sulfonic acid derivatives. Based on the esterification reaction with methanol in the presence of sulfuric acid, 5-indolylmethylenerhodanine-3-propanic acid was transformed into appropriate ester for further evaluation of antimicrobial activity. The antimicrobial activity screening allowed the identification of compounds with significant effect against Escherichia coli, Staphylococcus lentus and Candida albicans with [the] MIC/MBC/MFC values in the range of 25-50 μg/mL. Conclusions. The synthesized 5-indolylmethylenerhodanine-3-carboxylic/sulfonic acid derivatives are a convenient platform for the development of new highly active and low-toxic agents as potential drug-like molecules with antimicrobial activity.
Keywords: synthesis, 2-thioxo-4-thiazolidinone, indolecarbaldehydes, spectral data, antimicrobial activity

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