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  Conformationally constrained analogues of (Z)-5-decenyl acetate, a pheromone component of Agrotis segetum

Jonsson, S., Hansson, B., & Liljefors, T. (1996). Conformationally constrained analogues of (Z)-5-decenyl acetate, a pheromone component of Agrotis segetum. Bioorganic & Medicinal Chemistry, 4(3), 499-504. doi:10.1016/0968-0896(96)00032-6.

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EXT235.pdf (Publisher version), 555KB
 
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Jonsson, S, Author
Hansson, Bill1, Author           
Liljefors, T, Author
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1External Organizations, ou_persistent22              

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Free keywords: SINGLE-SENSILLUM RECORDINGS; TURNIP MOTH; SEX-PHEROMONE; MOLECULAR MECHANICS; CHAIN; LEPIDOPTERA; NOCTUIDAE; RECEPTOR; SCHIFFstructure-activity; Agrotis segetum; cyclic analogues; single-cell recordings; pheromone component;
 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 1) or five-membered (6) ring system. These cyclic 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. Copyright (C) 1996 Elsevier Science Ltd

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Language(s): eng - English
 Dates: 1996-03
 Publication Status: Issued
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 Rev. Type: -
 Identifiers: DOI: 10.1016/0968-0896(96)00032-6
Other: EXT235
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Title: Bioorganic & Medicinal Chemistry
  Other : Bioorg. Med. Chem.
Source Genre: Journal
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Publ. Info: Oxford, England : Pergamon
Pages: - Volume / Issue: 4 (3) Sequence Number: - Start / End Page: 499 - 504 Identifier: ISSN: 0968-0896
CoNE: https://pure.mpg.de/cone/journals/resource/954925582193