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Fluoro-Olefins as Peptidomimetic Inhibitors of Dipeptidyl Peptidases
Open accessAbstract
The feasibility of the fluoro-olefin function as a peptidomimetic group in inhibitors for dipeptidyl peptidase IV and II (DPP IV and DPP II) is investigated by evaluation of N-substituted Gly-Psi[CF=C]pyrrolidines, Gly-Psi[CF=C]piperidines, and Gly-Psi[CF=C](2-cyano)pyrrolidines. Of this later class, the (Z)- and (E)-fluoro-olefin analogues were prepared and chemical stability in comparison with the parent amide was checked. Most of these compounds exhibited a strong binding preference toward DPP II with IC(50) values in the low micromolar range, while only low DPP IV inhibitory potential is seen.
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Cited by
Direct electrochemical defluorinative carboxylation of α-CF 3 alkenes with carbon dioxide
Gao, X.-T., Zhang, Z., Wang, X., Tian, J.-S., Xie, S.-L., Zhou, F., & Zhou, J. (2020) · Chemical Science · doi:10.1039/d0sc04091f · Cited by 142
Metadata
- Authors
- Van der Veken, P., Senten, K., Kertèsz, I., De Meester, I., Lambeir, A.-M., Maes, M.-B., Scharpé, S., Haemers, A., & Augustyns, K.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-08-26
- Volume
- 48
- Issue
- 6
- Pages
- 1768-1780
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2041914199
- Cited by
- 183
- References
- 0
- FWCI
- 3.80
- Type
- journal article
- Language
- en
- Open access
- green
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- Van der Veken, P., Senten, K., Kertèsz, I., De Meester, I., Lambeir, A.-M., Maes, M.-B., Scharpé, S., Haemers, A., & Augustyns, K. (2005). Fluoro-Olefins as Peptidomimetic Inhibitors of Dipeptidyl Peptidases. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm0495982
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