Delta(2)-oxazolines-1,3 and N-acylaziridines as potential proinsecticides of carboxylic acids
| Autor: | Martine Beaufour, S Hamm, A Carlin-Sinclair, J.-C. Cherton |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
chemistry.chemical_classification
Chromatography biology 010405 organic chemistry Carboxylic acid 010401 analytical chemistry Substituent General Chemistry Metabolism Oxazoline biology.organism_classification 01 natural sciences Thin-layer chromatography 0104 chemical sciences chemistry.chemical_compound Hydrolysis chemistry Carboxylate Locust |
| Zdroj: | Journal of Chromatography B: Biomedical Sciences and Applications. 761:35-45 |
| ISSN: | 0378-4347 |
| DOI: | 10.1016/s0378-4347(01)00295-x |
| Popis: | Modern thin-layer chromatography (TLC) was used for the evaluation of delta2-oxazolines-1,3 I and N-acylaziridine VII structures, as potential proinsecticides of carboxylic acids III. Thus the unmasking2 of the active principles III from delta2-oxazolines-1,3 Ia-c and N-acylaziridine VIIc was monitored by spotting aliquots directly onto RP-18 TLC plates, without any sample pretreatment during in vitro assays performed in concentrated locust tissues. To achieve a good separation of carboxylate IIIa from endogenous components of the tissues, a short preliminary development with methanol or ion-pairing was necessary. From UV-TLC chromatograms (densitograms) it appeared that in a phosphate buffer at pH 7.4, the oxazoline Ia with a C2 substituent devoid of alpha-ramification or alpha,beta-insaturation hydrolysed slowly into the corresponding beta-hydroxylamide VIa and intermediate aminoester Va. Significantly, locust mesenteron (or fat body) efficiently triggered the unmasking of IIIa, a transformation which corresponds to the expected proinsecticide behavior of Ia. Conducting TLC monitoring in the same locust tissues also revealed that the oxazolines Ib and Ic with an alpha-ramification and an alpha,beta-insaturation, respectively, cannot be considered as proinsecticides of the corresponding carboxylic acids IIIb and IIIc. In contrast, the N-acylaziridine VIIc appeared as a convenient proinsecticide structure for masking the carboxylic acid IIIc. |
| Databáze: | OpenAIRE |
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