Synthesis of 2-(2-aminopyrimidine)-2,2-difluoroethanols as potential bioisosters of salicylidene acylhydrazides.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Markus K DahlgrenMikael Elofsson

Abstract

Salicylidene acylhydrazides are inhibitors of type III secretion in several gram-negative pathogens. To further develop the salicylidene acylhydrazides, scaffold hopping was applied to replace the core fragment of the compounds. The novel 2-(2-amino-pyrimidine)-2,2-difluoroethanol scaffold was identified as a possible analog to the salicylidene acylhydrazide core structure. The synthesis of a library of 2-(2-amino-pyrimidine)-2,2-difluoro-ethanols is described in this paper.

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Citations

Mar 3, 2015·Expert Opinion on Drug Discovery·Nuno Charro, Luís Jaime Mota
Apr 25, 2012·Bioorganic & Medicinal Chemistry Letters·Per-Anders EnquistMikael Elofsson
Sep 30, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·J Mikael HillgrenMikael Elofsson

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

Macromodel
SHOP
SciFinder
MOE

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