synthesis of 2-(2-aminopyrimidine)-2,2-difluoroethanols as potential bioisosters of salicylidene acylhydrazides合成2 -(2-aminopyrimidine)2,2-difluoroethanols的潜在bioisosters salicylidene acylhydrazides.pdfVIP

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synthesis of 2-(2-aminopyrimidine)-2,2-difluoroethanols as potential bioisosters of salicylidene acylhydrazides合成2 -(2-aminopyrimidine)2,2-difluoroethanols的潜在bioisosters salicylidene acylhydrazides.pdf

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synthesis of 2-(2-aminopyrimidine)-2,2-difluoroethanols as potential bioisosters of salicylidene acylhydrazides合成2 -(2-aminopyrimidine)2,2-difluoroethanols的潜在bioisosters salicylidene acylhydrazides

Molecules 2010, 15, 4423-4438; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of 2-(2-Aminopyrimidine)-2,2-difluoroethanols as Potential Bioisosters of Salicylidene Acylhydrazides Markus K. Dahlgren, Christopher T. Öberg, Erika A. Wallin, Pär G. Janson and Mikael Elofsson * Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden * Author to whom correspondence should be addressed; E-Mail: mikael.elofsson@chem.umu.se; Tel.: +46-90-7869328. Received: 19 May 2010; in revised form: 11 June 2010 / Accepted: 17 June 2010 / Published: 21 June 2010 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. Keywords: scaffold hopping; Reformatsky reaction; salicylidene acylhydrazide; type III secretion 1. Introduction Type III secretion (T3S) is a virulence system found in several clinically important Gram-negative pathogens including Yersinia spp., Chlamydia spp., Shigella spp., Salmonella spp., Pseudomonas aeruginosa, and enteropathogenic and enterohaemorrhag