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  • A new series of antibacterial nitrosopyrimidines: synthesis and structure-activity relationship.

A new series of antibacterial nitrosopyrimidines: synthesis and structure-activity relationship.

Archiv der Pharmazie (2014-11-22)
Monica Olivella, Antonio Marchal, Manuel Nogueras, Manuel Melguizo, Beatriz Lima, Alejandro Tapia, Gabriela E Feresin, Oscar Parravicini, Fernando Giannini, Sebastián A Andujar, Justo Cobo, Ricardo D Enriz
ABSTRACT

New nitrosopyrimidines were synthesized and evaluated as potential antibacterial agents. Different compounds structurally related with 4,6-bis(alkyl or arylamino)-5-nitrosopyrimidines were evaluated. Some of these nitrosopyrimidines displayed significant antibacterial activity against human pathogenic bacteria. Among them compounds 1c, 2a-c, and 9a-c exhibited remarkable activity against methicillin-sensitive and -resistant Staphylococcus aureus, Escherichia coli, Yersinia enterocolitica, and Salmonella enteritidis. A detailed structure-activity relationship study, supported by theoretical calculations, aided us to identify and understand the minimal structural requirements for the antibacterial action of the nitrosopyrimidines reported here. Thus, our results have led us to identify a topographical template that provides a guide for the design of new nitrosopyrimidines with antibacterial effects.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-Amino-2,6-dimethoxypyrimidine, 97%
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.5 wt. % silver wire as stabilizer
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS
Sigma-Aldrich
Potassium bromide, BioUltra, ≥99.5% (AT)
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
2-Amino-4,6-dimethoxypyrimidine, 98%
Supelco
Tetramethylsilane, analytical standard, for NMR spectroscopy, ACS reagent
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.1 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, anhydrous
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.05 % (v/v) TMS
Sigma-Aldrich
Potassium bromide, anhydrous, powder, 99.999% trace metals basis
Sigma-Aldrich
Potassium bromide, anhydrous, powder, 99.95% trace metals basis
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Potassium bromide, BioXtra, ≥99.0%
Sigma-Aldrich
Potassium bromide, ACS reagent, ≥99.0%
Sigma-Aldrich
Chloroform-d, "100%", 99.95 atom % D
Sigma-Aldrich
Tetramethylsilane, ≥99.0% (GC)
Sigma-Aldrich
Tetramethylsilane, electronic grade, ≥99.99% trace metals basis
Sigma-Aldrich
Tetramethylsilane, ACS reagent, NMR grade, ≥99.9%
Sigma-Aldrich
Potassium bromide, ReagentPlus®, ≥99.0%
Sigma-Aldrich
Potassium bromide, anhydrous, free-flowing, Redi-Dri, ReagentPlus®, ≥99%
Sigma-Aldrich
Potassium bromide, anhydrous, free-flowing, Redi-Dri, ACS reagent, ≥99%
Sigma-Aldrich
Potassium bromide, FT-IR grade, ≥99% trace metals basis