TY - JOUR
T1 - Structure and octopaminergic-agonist activity of 2-(arylimino)oxazolidines and 2-(substituted benzylamino)-2-oxazolines
AU - Hirashima, Akinori
AU - Pan, Canping
AU - Tomita, Jun
AU - Kuwano, Eiichi
AU - Taniguchi, Eiji
AU - Eto, Morifusa
N1 - Funding Information:
We thank Emeritus Professor Toshio Fujita of Kyoto University and Tanabe Pharmacology Co. Japan for donating the QSAR program. We are grateful to Professor Takaaki Sonoda of the Institute of Advanced Material Study, Kyushu University, Japan for allowing us to use the CAChe Groups-erver IBM RS6000. We also thank MicroSimulations Co. for providing the evaluation project for PowerFit 1.0 and related MicroSimulation software. This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, and Culture of Japan.
PY - 1997/7
Y1 - 1997/7
N2 - 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.
AB - 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.
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U2 - 10.1006/pest.1997.2302
DO - 10.1006/pest.1997.2302
M3 - Article
AN - SCOPUS:0031177823
SN - 0048-3575
VL - 58
SP - 219
EP - 228
JO - Pesticide Biochemistry and Physiology
JF - Pesticide Biochemistry and Physiology
IS - 3
ER -