Synthesis of (E)- and (Z)-fluoro-olefin analogues of potent dipeptidyl peptidase IV inhibitors

Tetrahedron Letters

Volumn 44, Issue 33, 2003, Pages 6231-6234

  Van Der Veken, Pieter ^a   Kertèsz, István ^a   Senten, Kristel ^a   Haemers, Achiel ^a   Augustyns, Koen ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMIDE; DIPEPTIDYL PEPTIDASE IV INHIBITOR; ENZYME INHIBITOR; FLUORINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HORNER WADSWORTH EMMONS REACTION; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION OPTIMIZATION;

EID: 0042848837     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01542-9     Document Type: Article

References (14)

1. Augustyns K., Bal G., Thonus G., Belyaev A., Zhang X.M., Bollaert W., Lambeir A.M., Durinx C., Goossens F., Haemers A. Curr. Med. Chem. 6:1999;311-327.
2. Fischer G., Heins J., Barth A. Biochim. Biophys. Acta. 742:1983;452-462.
3. (a) Abraham M.J., Ellison S.L.R., Schonholzer P., Thomas W.A. Tetrahedron. 42:1986;2101-2110
4. Biomedical Frontiers of Fluorine Chemistry; Cieplak, P.; Kollman, P. A.; Radomski, J. P. ACS Symp. Ser. 639; American Chemical Society: Washington, DC, 1996, 143-156.
5. Welch J.T., Lin J. Tetrahedron. 52:1996;291-304.
6. Lin J., Toscano P.J., Welch J.T. Proc. Natl. Acad. Sci. USA. 95:1998;14020-14024.
7. (c) Zhao K., Lim D.S., Funaki T., Welch J.T. Bioorg. Med. Chem. 11:2003;207-215
8. Biomedical Frontiers of Flourine Chemistry; Welch J. T.; Lin, J.; Boros, L. G.; DeCorte, B.; Bergmann, K.; Gimi, R. ACS Symp. Ser. 639; American Chemical Society: Washinton, DC, 1996, 129-142.
9. (a) Villhauer E.B., Brinkman J.A., Naderi G.B., Dunning B.E., Mangold B.L., Mone M.D., Russel M.E., Weldon S.C., Hughes T.E. J. Med. Chem. 45:2002;2362-2365
10. (b) Hughes, T. E.; Russel, M. E.; Bolognese, L.; Li, X.; Burkey, B. F.; Wang, P. R.; Villhauer, E. B. NVP-LAF237, A Highly Selective and Long-Acting Dipeptidyl Peptidase IV Inhibitor, Abstracts from the ADA 62nd Scientific Sessions; 62nd Annual Meeting and Scientific Sessions, San Francisco, 6/14-6/18; American Diabetes Association: Washington, DC, 2002; 272-OR, A67.
11. Villhauer, E. B. US Patent 6,124,305, 2000.
12. Burton D.J., Yang Z.Y., Qiu W.M. Chem. Rev. 96:1996;1641-1715.
13. 4-reduction of the resulting Weinreb-amide. During the reduction, no defluorination occurred. E- and Z-isomers were separated by silica gel flash chromatography, using hexanes/ethylacetate 49:1 as the eluent.
14. Bartlett P.A., Otake A. J. Org. Chem. 60:1995;3107-3111.