Abstract
A simple approach to synthesize new highly substituted 4H-pyran derivatives is described. Efficient Et3N acts as a readily accessible catalyst of this process performed in pure water and with only a 20 mol% of catalyst loading. The extremely simple operational methodology, short reaction times, clean procedure and excellent product yields render this new approach extremely appealing for the synthesis of 4H-pyrans, as potentially biological scaffolds. Additionally, DNA interaction analysis reveals that 4H-pyran derivatives behave preferably as minor groove binders over major groove or intercalators. Therefore, this is one of the scarce examples where pyrans have resulted to be interesting DNA binders with high binding constants (Kb ranges from 1.53 × 104 M−1 to 2.05 × 106 M−1).
Highlights
Functionalized 4H-pyrans are an important family of oxygen-containing heterocycles with a wide spectrum of biological properties
In agreement with all these aspects, we report the development of more efficient and sustainable protocols for the synthesis of highly functionalized 4H-pyrans via base catalysis
After an extensive screening of the reaction conditions such as solvents, base catalysts, the concentration of the reagents and time, among others, the scope of this process was explored for the synthesis of highly substituted 4H-pyrans 3
Summary
Functionalized 4H-pyrans are an important family of oxygen-containing heterocycles with a wide spectrum of biological properties. The variations observed in the position and intensity of the DNA peak at 260 nm are measured and the data processed to obtain binding constants and hints about the plausible interaction modes[85]. In order to elucidate the binding mode of 4H-pyran 3n with ctDNA, three experiments of fluorescence quenching have been performed.
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