ELECTROSTATIC AND STEREOCHEMICAL ASPECTS OF INSECT JUVENILE-HORMONE ACTIVE COMPOUNDS - A CLUE FOR HIGH-ACTIVITY

The electrostatic potentials were computed for a variety of functional groups found in active insect juvenile hormone (JH) mimetics; they are nonaromatic ester, carbamate, and oxime functions and aromatic phenyl, phenoxy, pyridyl, and pyridyloxy groups. The contours of the potentials commonly had a negative peak when viewed in the plane that perpendicularly bisects their skeletal plane. The site of the peak was at the position where the oxygen atom is located in the ethers, but in the multiatomic oximes it was at the nitrogen atom site rather than the oxygen site. In the benzene and pyridine functions, the negative peak was located at the site within the aromatic ring. The stereochemical interpretations made on the basis of this revealed that the most active members of the aromatic compounds are the entities the dimensions of which well fit the receptor cavity, and their negative peak is on the same site as that of the most active members of the nonaromatic classes of compounds. © 1990, American Chemical Society. All rights reserved.