1360651-89-3Relevant academic research and scientific papers
Synthesis and characterization of enantiomerically pure cis- and trans-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxides as γ- homoacetylcholine mimetics and inhibitors of acetylcholinesterase
Clerc, Christian,Rueedi, Peter
, p. 17 - 33 (2012/03/07)
The title compounds, the P(3)-axially and P(3)-equatorially substituted cis- and trans-configured 8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxides (=8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphabicyclo[4.4.0]decane 3-oxides=2-fluorohexahydro-6-(phenylmethyl)-4H-1,3,2-dioxaphosphorino[5,4-c] pyridine 2-oxides) were prepared (ee>98%) and fully characterized (Schemes2 and 3). The absolute configurations were established from that of their precursors, the enantiomerically pure cis- and trans-1-benzyl-4- hydroxypiperidine-3-methanols which were unambiguously assigned. Being configuratively fixed and conformationally constrained phosphorus analogues of acetyl γ-homocholine (=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. Copyright
