Synthesis and anticancer activity of some novel 5,6-fused hybrids of juglone based 1,4-naphthoquinones

Influence of lipophilicity in O‐acyl and O‐alkyl derivatives of juglone and lawsone: a structure–activity relationship study in the search for natural herbicide models

“…Additionally, a good correlation of log(1/IC 50 ) and logP was observed for 5‐ O ‐acyl derivatives 2 – 8 on cress for the root and shoot length parameters. A regression coefficient of R = 0.8503 was obtained for root length. Compound 3 did not fit the correlation and, consequently, it was not included in the regression (Fig.…”

“…5‐ O ‐alkyl juglones showed a good regression coefficient ( R = 0.8040). Compounds 27 , 35 and 36 did not fit the correlation or they showed high lipophilicity values and consequently they were excluded from the regression.…”

“…Despite this, 2‐ O ‐alkyl lawsones would be expected to be more resistant to hydrolysis than the 2‐ O ‐acyl lawsones to provide compounds that are more active than lawsone. A good correlation for 2‐ O ‐alkyl derivatives with a regression coefficient of R = 0.8944 was obtained (Fig. ).…”

“…They generally contain hydroxyl and/or methyl groups as substituents, although they can also be found joined to monosaccharides. In addition to their properties as natural pigments, a broad range of biological activities have been described for these compounds, for example, antifungal, phytotoxic, anti‐inflammatory, antioxidant and anticancer properties . These effects are mainly ascribed to the ability of naphthoquinones to generate reactive oxygen species (ROS) and also the electrophilicity of the quinone moiety in reactions with different biological targets through a 1,4‐Michael addition involving the nucleophilic thiol species, proteins, DNA and RNA …”

Design of etoposide polymeric forms

“…Then, the modified assay procedure given in EP 7.0 was used. [20]. Determination was performed in a gradient mode on a Waters Breeze chromatographic system.…”