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Structure-activity relationship observations of trans-trimedlure enantiomers

Author:
Warthen, J.D. Jr., Schmidt, W.F., Doolittle, R.E., Cunningham, R.T.
Source:
Journal of chemical ecology 1995 v.21 no.1 pp. 69-79
ISSN:
0098-0331
Subject:
trimedlure, enantiomers, mixtures, structure-activity relationships, simulation models, Ceratitis capitata, insect control
Abstract:
tert-Butyl 4- (and 5-) chloro-trans-2-methylcyclohexane-1 -carboxylate (TML), a mixture of four major trans and four minor cis isomers, is used as an attractant for detecting and monitoring the male Mediterranean fruit fly (medfly), Ceratitis capitata (Wiedemann). The eight isomers (racemic mixtures) were isolated by HPLC, and their relative attractiveness in the field was determined. A quantitative structure-activity relationship (QSAR) was proposed that related a molecular measurement (angstrom3) of the TML structure to male medfly captures. More recently, the trans-TML enantiomers were synthesized in sufficient quantities for field testing. This paper reports the computer-aided molecular modeling, via Chem-X, of the trans-TML enantiomers and the staggered and superimposed fitting with the most attractive isomer, (1S,2S,4R)-TML-C, to determine common volumes and surface areas from Van der Waals (VdW) maps. Observations of structure-activity relationships (SAR) are reported for the staggered fittings.
Agid:
2674069