C. Clerc
2012
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Abstract
The title compounds, the P(3)-axially and P(3)-equatorially substituted cisand trans-configured 8benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxides (1⁄4 8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphabicyclo[4.4.0]decane 3-oxides1⁄4 2-fluorohexahydro-6-(phenylmethyl)-4H-1,3,2-dioxaphosphorino[5,4-c]pyridine 2-oxides) were prepared (ee> 98%) and fully characterized (Schemes 2 and 3). The absolute configurations were established from that of their precursors, the enantiomerically pure cisand trans-1-benzyl-4-hydroxypiperidine-3-methanols which were unambiguously assigned. Being configuratively fixed and conformationally constrained phosphorus analogues of acetyl g-homocholine (1⁄4 3(acetyloxy)-N,N,N-trimethylpropan-1-aminium), they are suitable probes for the investigation of molecular interactions with acetylcholinesterase. As determined by kinetic methods, all of the compounds are weak inhibitors of the enzyme.