The synthesis and biological activity of lipophilic derivatives of bicine conjugated with N³-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid (FMDP)—an inhibitor of glucosamine-6-phosphate synthase

Abstract

A series of bis-N,N-(2-hydroxyethyl)glycine (bicine) derivatives, conjugated with an inhibitor of glucosamine-6-phosphate synthase, have been synthesized and their lipophilic and antifungal properties have been tested. The obtained compounds demonstrated higher lipophilicity than free inhibitor (FMDP) and, in consequence, an increased potential to cross the cytoplasmic membrane. All the tested compounds show better antifungal activity than parent compound.

Keywords::

• Antifungal agents
• FMDP derivatives
• prodrug

Acknowledgments

This work was supported by the Ministry of Education and Science (Grant No. NN 405 1829 35). The HPLC instrument (which was used in this study) is a part of equipments of The Research Laboratory Center of Excellence “ChemBioFarm.” Its purchase was partially funded by the European Union Structural Funds under the Sectoral Operational Programme—Improvement of the Competitiveness of Enterprises.

Declaration of interest

The authors report no conflicts of interest.