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Synthesis and Characterization of Enantiomerically Pure cis- and trans-3-Fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-Oxides as Acetylcholine Mimetics and Inhibitors of Acetylcholinesterase

✍ Scribed by Piergiorgio Lorenzetto; Michael Wächter; Peter Rüedi

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
580 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The title compounds, the P(3)‐axially and P(3)‐equatorially substituted cis‐ and trans‐configured 9‐benzyl‐3‐fluoro‐2,4‐dioxa‐9‐aza‐3‐phosphadecalin 3‐oxides (=9‐benzyl‐3‐fluoro‐2,4‐dioxa‐9‐aza‐3‐phosphabicyclo[4.4.0]decane 3‐oxides=7‐benzyl‐2‐fluorohexahydro‐4__H__‐1,3,2‐dioxaphosphorino[4,5‐c]pyridine 2‐oxides) were prepared (ee >99%) and fully characterized (Schemes 2 and 4). The absolute configurations were deduced from that of their precursors, the enantiomerically pure ethyl 1‐benzyl‐3‐hydroxypiperidine‐4‐carboxylates and 1‐benzyl‐3‐hydroxypiperidine‐4‐methanols which were unambiguously assigned. Being configuratively fixed and conformationally constrained phosphorus analogues of acetylcholine, the title compounds represent acetylcholine mimetics and are suitable probes for the investigation of molecular interactions with acetylcholinesterase. As determined by kinetic methods, all of the compounds are moderate irreversible inhibitors of the enzyme.

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