A Quantum Chemical Study of Insect Juvenile Hormone Mimics: The Active Conformation and the Electrostatic Similarities

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Abstract
The stable conformations and the electrostatic properties of insect juvenile hormone (JH) mimics are studied using semi‐empirical molecular orbital methods. One of the minimum energy conformations of JH active diphenylethers, a new class of JH mimics, is found to be superimposable on the stable extended structure of methoprene which is one of the most highly active JH mimics within the series of terpenoid compounds. As well as the superimposability of the diphenylether and terpenoid structures, JH active functional groups such as esters, carbamates and oxime O‐ethers are also shown to be superimposable. The electrostatic potentials of these functional groups which are commonly found in the diphenylethers and the terpenoid JH mimics are similar to each other in terms of potential contours and the similarity indices of electrostatic potentials. This may account for the bioisosterism of these active functional groups. Here we postulate a model of molecular recognition at the JH receptor in which the electrostatic interaction is important as well as the size and shape of the molecule. The molecular similarities between different classes of JH mimics in terms of steric and electrostatic properties, which are derived from quantum chemical methods, may help to understand the universality of active structures and aid in the design of new active generations.