Efficient catalytic oxidation of 3-arylthio- and 3-cyclohexylthio-lapachone derivatives to new sulfonyl derivatives and evaluation of their antibacterial activities

Mariana F.Do C. Cardoso, Ana T.P.C. Gomes, Caroline Dos S. Moreira, Mário M.Q. Simões, Maria G.P.M.S. Neves, David R. Da Rocha, Fernando De C. Da Silva, Catarina Moreirinha, Adelaide Almeida, Vitor F. Ferreira, José A.S. Cavaleiro*, João Paulo C. Tomé

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

New sulfonyl-lapachones were efficiently obtained through the catalytic oxidation of arylthio- and cyclohexylthio-lapachone derivatives with hydrogen peroxide in the presence of a Mn(III) porphyrin complex. The antibacterial activities of the non-oxidized and oxidized lapachone derivatives against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus were evaluated after their incorporation into polyvinylpyrrolidone (PVP) micelles. The obtained results show that the PVP-formulations of the lapachones 4b-g and of the sulfonyl-lapachones 7e and 7g reduced the growth of S. aureus.

Original languageEnglish
Article number302
JournalMolecules
Volume22
Issue number2
DOIs
Publication statusPublished - Feb 2017
Externally publishedYes

Keywords

  • Antibacterial activity
  • Arylthio/cyclohexylthio-lapachones
  • Hydrogen peroxide
  • Oxidation
  • Polyvinylpyrrolidone
  • PorphyrinatoMn(III)
  • Sulfonyl-lapachones

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