Synthesis and biological evaluation of novel ethyl 2-amino-6-ferrocenyl-1,6-dihydropyrimidine-5-carboxylates and ethyl 2-amino-6-ferrocenylpyrimidine-5-carboxylates

Three-Component Reaction of Tautomeric Amidines with 3-Ferrocenylmethylidene-2,4-pentanedione. Formation of Polymeric Coordination Complexes of Potassium Ferrocenyl-(hexahydro)pyrimidoxides

“…We have recently reported the synthesis of ethyl-2-aryl(methyl)- and 2-amino-6-ferroce-nyl(dihydro)pyrimidine-4-carboxylates with high anticarcinogenic activity [16] via the reaction between ethyl-2-acyl-3-ferrocenyl acrylates with amidines. Bioactive ferrocenyl(dihydro)pyrimidines with ethoxycarbonyl substituents in the heterocyclic nuclei were isolated with yields about 40%–45%, together with the products of several side processes: fragmentations of the initial ethyl 2-acyl-3-ferrocenyl acrylates, 1,3-insertion of amidines into ferrocenyl acrylates [16,17,18], etc . However, despite the comparatively low yields of ferrocenyl(dihydro)pyrimidines, the high bioactivity of the latter compounds evoked our interest in a more detailed investigation of the interaction between ferrocenyl-containing β-dicarbonyl compounds and nitrogen polynucleophiles.…”

Evaluation of Antibacterial Functionalized Dihydropyrimidine Photoaffinity Probes Toward Mechanism of Action Studies

“…As pyrimidine rings are the chief chemical motif known to produce DHFR inhibition, and literature accounts of dihydropyrimidine inhibition of DHFR exist, we considered that a DHP could be oxidized by air or under assay conditions to a pyrimidine, which may have caused the previously reported DHFR inhibition. To explore this, oxidization of DHP 7a to the pyrimidine 8a was performed using phenyliodine diacetate (PIDA) (Figure a), − as this oxidation state mimics FDA approved antimicrobial DHFR inhibitors trimethoprim 1 (Figure a) and pyrimethamine 9 (Figure b). When 8a was screened for antibacterial activity, however, it was found to have no impact on the growth of S. aureus at concentrations up to 64 μg/mL.…”