Molecular similarity analysis between insect juvenile hormone and N, N-diethyl-m-toluamide (DEET) analogs may aid design of novel insect repellents.

摘要: Molecular similarity analysis of stereoelectronic properties between natural insect juvenile hormone (JH), -a synthetic mimic (JH-mimic, undecen-2-yl carbamate), and N, N-diethyl-m-toluamide (DEET) its analogs reveals similarities that may aid the design more efficacious repellents give a better insight into mechanism repellent action. The study involves quantum chemical calculations using AM1 semi-empirical computational method enabling conformational search for lowest most abundant energy conformers JH, JH-mimic, 15 DEET compounds, followed by complete geometry optimization conformers. Similarity analyses such as structural parameters, atomic charges, dipole moments, molecular electrostatic potentials, highest occupied orbital (HOMO) unoccupied (LUMO) energies were performed on JH-mimic compounds. attributes amide/ester moiety, negative potential regions beyond van der Waals surface, large distribution hydrophobic in compounds appear to be three important factors leading similar interaction with JH receptor. profiles surface is likely play crucial role recognition receptor from distance. This also suggests bioisosterism amide group and, thus, model at property thus attributed conflict complementarity binding sites.