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)
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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 > School of Infection & Immunity |
| 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 |
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