Dipeptidyl α-fluorovinyl Michael acceptors: Synthesis and activity against cysteine protease

Steert, K., El-Sayed, I., Van der Veken, P., Krishtal, A., Van Alsenoy, C., Westrop, G. D., Mottram, J. C. , Coombs, G. H., Augustyns, K. and Haemers, A. (2007) Dipeptidyl α-fluorovinyl Michael acceptors: Synthesis and activity against cysteine protease. Bioorganic and Medicinal Chemistry Letters, 17(23), pp. 6563-6566. (doi:10.1016/j.bmcl.2007.09.075)

Full text not currently available from Enlighten.

Publisher's URL: http://dx.doi.org/10.1016/j.bmcl.2007.09.075

Abstract

The synthesis of novel dipeptidyl α-fluorovinyl sulfones using a Horner–Wadsworth–Emmons approach on N-Boc-l-phenylalaninal is described. Inhibitory assays against a Leishmania mexicana cysteine protease (CPB2.8ΔCTE) revealed low biological activity. Relative rates of Michael additions of 2′-(phenethyl)thiol with vinyl sulfone and α-fluorovinyl sulfone were determined, and ab initio calculations on several Michael acceptor model structures were performed; both were in agreement with the biological testing.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Westrop, Mr Gareth and Mottram, Professor Jeremy
Authors: Steert, K., El-Sayed, I., Van der Veken, P., Krishtal, A., Van Alsenoy, C., Westrop, G. D., Mottram, J. C., Coombs, G. H., Augustyns, K., and Haemers, A.
College/School:College of Medical Veterinary and Life Sciences > Institute of Infection Immunity and Inflammation
Journal Name:Bioorganic and Medicinal Chemistry Letters
Journal Abbr.:Bioorganic. Med. Chem. Lett.
Publisher:Elsevier
ISSN:0960-894X
ISSN (Online):1464-3405
Published Online:28 September 2007
Related URLs:

University Staff: Request a correction | Enlighten Editors: Update this record

Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
297261Post-genomic analysis of cysteine protease function in Leishmania parasitesJeremy MottramMedical Research Council (MRC)G0000508Infection Immunity and Inflammation Life Sciences