Antimicrobial Activity of Substituted Benzopentathiepin-6-amines

Tatyana M. Khomenko, Dina V. Korchagina, Dmitry S. Baev, Pavel M. Vassiliev, Konstantin P. Volcho, Nariman F. Salakhutdinov

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A number of substituted benzopentathiepin-6-amines and their analogues without a polysulfur ring were synthesized and evaluated in vitro for antimicrobial activity against a panel of reference bacterial and fungal strains. Trifluoroacetamide 14 demonstrated high antibacterial activity against Staphylococcus aureus (MRSA strain) with a MIC of 4 μg/mL, which was four-fold higher than the activity of a reference drug amoxicillin. This compound was also most active against the Candida albicans fungus (MIC of 1 μg ml−1), whereas amide 17 containing a morpholine substituent was most active against the Cryptococcus neoformans fungus (MIC of 2 μg ml−1). These compounds have no hemolytic activity and are low cytotoxic. Replacement of the pentathiepine ring with 1,3-dithiolan-2-one or 1,3-dithiolane moieties leads to loss of antimicrobial activity. Based on the QSAR analysis and molecular docking data, bacterial DNA ligase might be one of the targets for the antibacterial activity of substituted benzopentathiepin-6-amines against S. aureus.

Original languageEnglish
Pages (from-to)590-599
Number of pages10
JournalJournal of Antibiotics
Volume72
Issue number8
DOIs
Publication statusPublished - 1 Aug 2019

Keywords

  • DNA-LIGASE INHIBITORS
  • BIOLOGICAL EVALUATION
  • NATURAL-PRODUCTS
  • DRUG DISCOVERY
  • IN-VITRO
  • VARACIN
  • 8-(TRIFLUOROMETHYL)-1,2,3,4,5-BENZOPENTATHIEPIN-6-AMINE
  • ANALOGS
  • DESIGN

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