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Bioorg Med Chem

Title:		"Conformationally constrained analogues of (Z)-5-decenyl acetate, a pheromone component of Agrotis segetum"
Author(s):		Jonsson S; Hansson BS; Liljefors T;
Address:		"Department of Organic Chemistry, Chemical Center, Lund University, Sweden"
Journal Title:		Bioorg Med Chem
Year:		1996
Volume:		4
Issue:		3
Page Number:		499 - 504
DOI:		10.1016/0968-0896(96)00032-6
ISSN/ISBN:		0968-0896 (Print) 0968-0896 (Linking)
Abstract:		"Conformationally constrained analogues of (Z)-5-decenyl acetate (1), a pheromone component of the turnip moth, Agrotis segetum, have been synthesized and tested by using electrophysiological single-cell recordings. In the constrained analogues the terminal alkyl chain in 1 has been incorporated in a six-membered (3 and 4) or five-membered (6) ring system. These cycli compounds are also conformationally constrained analogues of the previously deduced bioactive conformations of the corresponding chain-elongated analogues 2 and 5. The electrophysiological activities of the constrained analogues are found to be significantly lower than that of the natural pheromone component 1, most probably due to steric repulsive interactions between the analogue and the receptor, and also lower than the activities of the corresponding chain-elongated analogues of 1. It is concluded that the flexibility of the terminal chains in 2 and 5 is essential for the possibility of the receptor to accommodate these parts of the chain-elongated analogues in their bioactive conformations"
Keywords:		"Acetates/*chemistry Animals Electrophysiology Models, Molecular Molecular Conformation Moths/*chemistry Sex Attractants/*chemistry Structure-Activity Relationship;"
Notes:		"MedlineJonsson, S Hansson, B S Liljefors, T eng Research Support, Non-U.S. Gov't England 1996/03/01 Bioorg Med Chem. 1996 Mar; 4(3):499-504. doi: 10.1016/0968-0896(96)00032-6"