The quantitative structure-activity relationship of 2-(arylimino)oxazolidines (AIOs) and 2-(substituted benzylamino)-2-oxazolines (SBOs) in stimulating adenylate cyclase prepared from thoracic nerve cords of the American cockroach Periplaneta americana L. was examined using parameters calculated by a molecular orbital procedure. The more hydrophobic and the smaller the highest occupied molecular orbital (HOMO) and molecular connection (MC) values, the greater the V(max) values. The larger similarity comparison (SC) values (the more similar structure to OA the compound has), the greater the V(max) values. The larger the molar refractivity (MR) and V(max) values, the greater the activity in term of K(a). 2-Alkyl, 4-halogen substitution in the phenyl ring of AIOs gave the greatest enzyme activation. Compounds incorporating a halogen(s) in the phenyl ring of SBO compounds favor octopaminergic-agonist activity. Superimposition of energy-minimized octopamine (OA) and 2-(2,3,4-trichlorophenylimino)oxazolidine (21) revealed structural and conformational similarities that might account for the high activity of 21 compared to the corresponding thiazolidine derivative, which is not superimposed well with OA.
!!!All Science Journal Classification (ASJC) codes