Synthesis and bioactivity of new phosphorylated R,R'-substituted sulfoximines.
R,R'-disubstituted sulfoximines were phosphorylated with O,O-diethylchloro phosphate and phosphorothionate to obtain new organophosphorus compounds. After purification they were characterized by GC-MS and (1)H-NMR. The toxicity of the synthesized O,O-diethyl N-(R,R'-disubstituted sulfoximine) phosphoro-amidothionates was assayed on Musca domestica. It was found that the methyl phenyl derivative was the most toxic compound, followed by the dipropyl and dibutyl derivatives. The dihexyl compound was the less toxic of all the assayed compounds, being one hundred times less toxic than a paraoxon standard The anticholinesterasic activity of the corresponding phosphoramidates was assayed on homogenates of house flies' heads, giving values similar to paraoxon for the methyl phenyl derivative.
Reinhard
Monica Bellozas
MB
Departamento de Química - FCEyN - Univ. Nac. La Pampa - Santa Rosa - Pcia. La Pampa - Argentina. bellozas@exactas.unlpam.edu.ar
de Licastro
Susana Arnstein
SA
D000110:Acetylcholinesterase / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D019328:Buthionine Sulfoximine / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008401:Gas Chromatography-Mass Spectrometry; D006793:Houseflies; D009682:Magnetic Resonance Spectroscopy; D008717:Methionine Sulfoximine / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010766:Phosphorylation; D013329:Structure-Activity Relationship
D004791:Enzyme Inhibitors; D009943:Organophosphorus Compounds; D008717:Methionine Sulfoximine; D019328:Buthionine Sulfoximine; D000110:Acetylcholinesterase