Conformational analysis, electronic properties and molecular electrostatic potential of nitrofurans derivatives with antibacterial activity

The present investigation includes a combined computational study using the Molecular Mechanics and Quantum Mechanics methods, in 5-nitrofurane derivatives aiming to find the structural, electronic and electrostatic requirements they need to elicit antibacterial activity. Among the structural and electronic requirements for a potent biological activity in these derivatives, there is a common spatial orientation that was named 'bioactive conformation', electronic deficiency, low energy and low electronic density in the LUMO, a negative electrostatic potential in both oxygens of the nitro group and in the nitrogenated ring present in the lateral chain over C2 and a positive electrostatic potential region from the nitrogen atom in the nitro group to the hydrogen atoms attached to the carbon atoms in the furane ring. (c) 2005 Elsevier B.V. All rights reserved.