Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

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 (K_b ranges from 1.53 × 10⁴ M^-1 to 2.05 × 10⁶ M^-1).