C-Triazolyl β-d-furanosides as LpxC inhibitors: stereoselective synthesis and biological evaluation

Autor:	Sunit Kumar Jana, Ralph Holl, Constantin G. Daniliuc, Marius Löppenberg
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Glycoside Ring (chemistry) Biochemistry Combinatorial chemistry Lipid A chemistry.chemical_compound chemistry Chiral pool synthesis Biosynthesis Drug Discovery Click chemistry Stereoselectivity Tetrahydrofuran
Zdroj:	Tetrahedron. 70:6569-6577
ISSN:	0040-4020
DOI:	10.1016/j.tet.2014.07.016
Popis:	C-Triazolyl β-d-furanosides 10a–f were synthesized in a stereocontrolled way, starting from d-mannose. In the key steps of the synthesis a diastereoselective reduction of hemiketal 14 and a Cu(I) catalyzed [3+2]-cycloaddition of central building block 18 with various azides were performed. The synthesized hydroxamic acids were tested for their inhibitory activity against LpxC, a Zn2+-dependent deacetylase playing an important role in the biosynthesis of lipid A and therefore representing an interesting target for the development of novel antibiotics against Gram-negative bacteria. The C-triazolyl glycosides 10a–f did not exhibit antibiotic activity. However, the described synthesis is a versatile way to access C-triazolyl β-d-furanosides bearing all of their substituents at the same side of the tetrahydrofuran ring.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::00491677de66ff6cd3b5eed34007edf3 https://doi.org/10.1016/j.tet.2014.07.016 Zobrazit plný text záznamu Full Text from ScienceDirect