Difluoropalmitic acids as potential inhibitors of the biosynthesis of the sex pheromone of the Egyptian armyworm Spodoptera littoralis—IV

Difluoropalmitic acids as potential inhibitors of the biosynthesis of the sex pheromone of the Egyptian armyworm Spodoptera littoralis—IV

2,2-, 3,3- and 4,4-Difluoropalmitic acids ( 1–3) have been synthesized and fully characterized. Acids 2 and 3 were prepared through fluorination of the corresponding dithioacetal-protected ketoesters followed by enzymatic saponification. The acids 1–3 were evaluated in vivo as inhibitors of the β-ox...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry Vol. 4; no. 3; pp. 467 - 472
Main Authors: Bosch, M.P., Pérez, R., Lahuerta, G., Hernanz, D., Camps, F., Guerrero, A.
Format: Journal Article
Language:English
Published: England Elsevier Ltd 01-03-1996
Subjects:
Animals
biosynthesis
Difluoropalmitic acids
Esters - metabolism
Fatty Acids - metabolism
Gas Chromatography-Mass Spectrometry
inhibition
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Palmitic Acids - pharmacology
Sex Attractants - antagonists & inhibitors
Sex Attractants - biosynthesis
sex pheromone
Spectroscopy, Fourier Transform Infrared
Spodoptera - drug effects
Spodoptera - metabolism
Spodoptera litoralis
Spodoptera litoralis
inhibition
sex pheromone
biosynthesis
Difluoropalmitic acids
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Summary:2,2-, 3,3- and 4,4-Difluoropalmitic acids ( 1–3) have been synthesized and fully characterized. Acids 2 and 3 were prepared through fluorination of the corresponding dithioacetal-protected ketoesters followed by enzymatic saponification. The acids 1–3 were evaluated in vivo as inhibitors of the β-oxidation step of the biosynthesis of ( Z, E)-9,11-tetradecadienyl acetate, the major component of the sex pheromone of the Egyptian armyworm Spodoptera littoralis. Only, the 2,2- and 3,3-derivatives, i.e. those containing the two fluorine atoms at the positions involved in the chain-shortened step, have been found to be active, the activity being similar to or lower than that displayed by the corresponding monofluorinated acids. Synthesis and biological activity of difluoroplasmitic acids 1–3 are presented.
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ISSN:0968-0896
1464-3391
DOI:10.1016/0968-0896(96)00027-2