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

Cardoso, Mariana F. C.; Gomes, Ana T. P. C.; Moreira, Caroline dos Santos; Simões, Mário M. Q.; Rocha, David R. da; Silva, Fernando De C. Da; Moreirinha, Catarina; Almeida, Adelaide; Ferreira, Vı́tor F.; Cavaleiro, José A. S.

doi:10.3390/molecules22020302

Cited by 8 publications

(2 citation statements)

References 47 publications

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“…The compounds containing sulfone showed significant inhibitory activities against Gram-negative (E. coli ATCC13706) and Gram-positive (S. aureus 2065 MA) bacteria. [20] Therefore, using a classical methodology based on RuCl 3 • H 2 O and NaIO 4 , [21] we converted some of the sulphurcontaining naphthoquinone derivatives prepared from lapachol (1) and C-allyl-lawsone (4) to their respective sulfones (Scheme 4). Compounds prepared from 3, were converted to their respective oxidised products (6 a-6 f) in high yields (71-94 %).…”

Section: Resultsmentioning

confidence: 99%

Electrochemical Sulphenylation/Cyclization of Quinones: A Rapid, Green, and Efficient Access to Cytotoxic Compounds

Diogo,

Delolo,

Graça

et al. 2023

Eur J Org Chem

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Undivided electrochemical cells enable economical preparation of sulphur‐containing naphthoquinones via electrochemical sulphenylation of quinoidal compounds. The environmentally friendly and efficient protocol eliminates the use of chemical oxidants and facilitates the synthesis of the desired molecules. This approach offers an efficient and versatile method to synthesize quinones that exhibit cytotoxic against cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Electrochemical Sulphenylation/Cyclization of Quinones: A Rapid, Green, and Efficient Access to Cytotoxic Compounds

Diogo,

Delolo,

Graça

et al. 2023

Eur J Org Chem

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“…VPD was selected as the monomer to prepare PVP formulations due to their already reported features, namely, pharmacokinetic and pharmacological properties, non-toxicity, and water-solubility of the obtained micelles [ 96 ]. This strategy allows to improve the hydrophilicity of biologically active drugs and is being efficiently used to solubilize neutral porphyrin-base PS in water with positive effects in photodynamic processes [ 97 , 98 , 99 , 100 ]. Moreover, this carrier demonstrated to be non-toxic for both normal and cancer cells after PDT treatment [ 100 ].…”

Section: Resultsmentioning

confidence: 99%

Unraveling the Photodynamic Activity of Cationic Benzoporphyrin-Based Photosensitizers against Bladder Cancer Cells

et al. 2021

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In this study, we report the preparation of new mono-charged benzoporphyrin complexes by reaction of the appropriate neutral benzoporphyrin with (2,2′-bipyridine)dichloroplatinum(II) and of the analogs’ derivatives synthesized through alkylation of the neutral scaffold with iodomethane. All derivatives were incorporated into polyvinylpyrrolidone (PVP) micelles. The ability of the resultant formulations to generate reactive oxygen species was evaluated, mainly the singlet oxygen formation. Then, the capability of the PVP formulations to act as photosensitizers against bladder cancer cells was assessed. Some of the studied formulations were the most active photosensitizers causing a decrease in HT-1376 cells’ viability. This creates an avenue to further studies related to bladder cancer cells.

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Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

Ravichandiran

Masłyk

Sheet³

et al. 2019

ChemistryOpen

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1,4‐Naphthoquinones are an important class of compounds present in a number of natural products. In this study, a new series of 1,4‐naphthoquinone derivatives were synthesized. All the synthesized compounds were tested for in vitro antimicrobial activity. In this present investigation, two Gram‐positive and five Gram‐negative bacterial strains and one pathogenic yeast strain were used to determine the antibacterial activity. Naphthoquinones tested for its antibacterial potencies, among seven of them displayed better antimicrobial activity against Staphylococcus aureus ( S. aureus ; 30–70 μg/mL). Some of the tested compounds showed moderate to low antimicrobial activity against Pseudomonas aeruginosa ( P. aeruginosa ) and Salmonella bongori ( S. bongori ; 70–150 μg/mL). In addition, most active compounds against S. aureus were evaluated for toxicity to human blood cells using a hemolysis assay. For better understanding, reactive oxygen species (ROS) generation, time‐kill kinetic study, and apoptosis, necrosis responses were investigated for three representative compounds.

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

Cited by 8 publications

References 47 publications

Electrochemical Sulphenylation/Cyclization of Quinones: A Rapid, Green, and Efficient Access to Cytotoxic Compounds

Electrochemical Sulphenylation/Cyclization of Quinones: A Rapid, Green, and Efficient Access to Cytotoxic Compounds

Unraveling the Photodynamic Activity of Cationic Benzoporphyrin-Based Photosensitizers against Bladder Cancer Cells

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

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