117765-69-2Relevant academic research and scientific papers
Synthese, complexation et mecanisme d'hydrolyse de sulfamoylacetates d'alkyle, inhibiteurs de l'alcool coniferylique deshydrogenase
Baltas, Michel,Cazaux, Louis,Blic, Arnold de,Gorrichon, Liliane,Tisnes, Pierre,Touati, Abdelkader
, p. 79 - 87 (2007/10/02)
Alkyl sulfamoylacetates and their derivatives, inhibitors of coniferylalcohol deshydrogenase (CADH), were prepared with 40-80percent yield either by oxidation of the corresponding alkyl sulfinamoylacetates or by reaction of functionnalised sulfonyl chlorides with amines.The kinetics of hydrolysis of methyl N-phenyl sulfamoylacetate 7 leads us to propose a BAC2 mechanism of slow hydroxide ion attack at the carbonyl carbon atom.It is different from that proposed for the basic hydrolysis of the alkylsulfinamoylacetates.Sulfamoylesters do not complex ZnBr2 in CHCl3 medium at the contrary of the sulfinamoylesters.The sites and the complexation constants have been found by 1H NMR, using shift reagent .The reaction of ZnBr2/THF with the tert-butyl esters of the titled compounds leads to the formation of the Zn2+ salt of the acid.These results have been correlated with the differences of biologic activity of these compounds during the inactivation of CADH.
