Reactivity of δ-substituted α,β-unsaturated cyclic lactones with antileishmanial activity

Abstract

The present study examines a set of 43 compounds for their antileishmanial activities and cytotoxicities. Negative lowest unoccupied molecular orbitas and similar values for the electrophilic Fukui function condensed at the β-position for a subset of δ-substituted α,β-unsaturated cyclic lactones classify them as strong Michael acceptors. There was a well-defined trend of increasing antileishmanial activity with increasing cytotoxicity and large selectivity indices for the most active compounds. Softer compounds were more active than harder ones as observed from the experimental data and rationalised by calculated reactivity indices.

Keywords::

• antileishmanial activity
• reactivity indices
• molecular descriptors

Acknowledgements

This work was partially funded by CODI office, Universidad de Antioquia, via ‘Estrategia de Sostenibilidad 2013–2014’.