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Molecules 2017, 22(2), 302; doi:10.3390/molecules22020302

Efficient Catalytic Oxidation of 3-Arylthio- and 3-Cyclohexylthio-lapachone Derivatives to New Sulfonyl Derivatives and Evaluation of Their Antibacterial Activities

1
Department of Chemistry and QOPNA, University of Aveiro, Aveiro 3810-193, Portugal
2
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Niterói 24020-150, RJ, Brazil
3
Department of Biology and CESAM, University of Aveiro, Aveiro 3810-193, Portugal
*
Authors to whom correspondence should be addressed.
Academic Editor: João Paulo C. Tomé
Received: 18 January 2017 / Revised: 6 February 2017 / Accepted: 13 February 2017 / Published: 16 February 2017
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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 4bg and of the sulfonyl-lapachones 7e and 7g reduced the growth of S. aureus. View Full-Text
Keywords: oxidation; porphyrinatoMn(III); hydrogen peroxide; arylthio/cyclohexylthio-lapachones; sulfonyl-lapachones; polyvinylpyrrolidone; antibacterial activity oxidation; porphyrinatoMn(III); hydrogen peroxide; arylthio/cyclohexylthio-lapachones; sulfonyl-lapachones; polyvinylpyrrolidone; antibacterial activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Cardoso, M.F.C.; Gomes, A.T.P.C.; Moreira, C.S.; Simões, M.M.Q.; Neves, M.G.P.M.S.; da Rocha, D.R.; da Silva, F.C.; Moreirinha, C.; Almeida, A.; Ferreira, V.F.; Cavaleiro, J.A.S. Efficient Catalytic Oxidation of 3-Arylthio- and 3-Cyclohexylthio-lapachone Derivatives to New Sulfonyl Derivatives and Evaluation of Their Antibacterial Activities. Molecules 2017, 22, 302.

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