1096144-75-0Relevant academic research and scientific papers
A new series of antibacterial nitrosopyrimidines: Synthesis and structure-activity relationship
Olivella, Monica,Marchal, Antonio,Nogueras, Manuel,Melguizo, Manuel,Lima, Beatriz,Tapia, Alejandro,Feresin, Gabriela E.,Parravicini, Oscar,Giannini, Fernando,Andujar, Sebastin A.,Cobo, Justo,Enriz, Ricardo D.
, p. 68 - 80 (2015)
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.
A switchable intramolecular hydrogen bond in polysubstituted 5-nitrosopyrimidines
Prochazkova, Eliska,Cechova, Lucie,Janeba, Zlatko,Dracinsky, Martin
, p. 10121 - 10133 (2013/11/06)
The formation of strong intramolecular hydrogen bonds was observed in a series of 2-amino-5-nitrosopyrimidines with alkylamino and arylamino substituents at positions 4 and 6. Mixtures of two rotamers differing in the orientation of the nitroso group were observed in the NMR spectra of the compounds where two distinct intramolecular hydrogen bonds could be formed. The ratio of the two rotamers depends strongly on the character of the substituents at positions 4 and 6 and can be finely tuned over a broad range of conformation ratios. The experimental results were supported by DFT calculations, which also made it possible to explain the apparent contradiction in the experimental dependence of the rotamer ratio on the Hammett constants for the arylamino substituents. The UV/vis spectra of the compounds also significantly depend on the nature of the substituents; however, the orientation of the nitroso group does not have any influence on the position of the absorption bands in the spectra.
Alkoxy-5-nitrosopyrimidines: Useful building block for the generation of biologically active compounds
Marchal, Antonio,Nogueras, Manuel,Sanchez, Adolfo,Low, John N.,Naesens, Lieve,De Clercq, Erik,Melguizo, Manuel
supporting information; experimental part, p. 3823 - 3830 (2010/10/04)
Several alkoxy-5-nitrosopyrimidines were synthesised and high regioselective and sequential nucleophilic aromatic substitution of methoxy groups in 2-am:ino-4,6-d.imetho;xy-5nitrosopyrimidine was observed. The approach was applied to the synthesis of valu
