Synthesis of Rigid Acetylcholine Mimics as Inhibitors of Serine Hydrolases

W. Ganci; U. Ringeisen; P. Rüedi

doi:10.3390/ecsoc-1-02032

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Site-Selective Incorporation of Thioamide-Linkages into a Growing Peptide via Variation of the 'Azirine/Oxazolone Method'

Synthesis of Rigid Acetylcholine Mimics as Inhibitors of Serine Hydrolases

W. Ganci

U. Ringeisen

P. Rüedi

¹ Institute of Organic Chemistry, University of Zurich,Winterthurerstrasse 190, CH-8057 Zurich, Switzerland

Published: 01 September 1997 by MDPI in The 1st International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-1-02032

Abstract: In continuation of our investigations concerning the regio- and stereo-chemical course of the inhibition of serine hydrolases (chymotrypsin, acetylcholinesterase) (F.A. Merckling, P. Rüedi, Chimia 1994, 48, 279) we have prepared conformationally restricted organophosphates of the cis- and trans-az(oni)adecaline type. Related compounds proved to be good probes for the investigation of stereochemical implications by 31P-NMR spectroscopy (W. Ganci, E.J.M. Meier, F.A. Merckling, G. Przibille, U. Ringeisen, P. Rüedi, Chimia 1996, 50, 345; iid. Helv. Chim. Acta, 1997, 80, 421).

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W. Ganci

U. Ringeisen

P. Rüedi