Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers

Unusual Reaction of Macrocyclic Uracils with Paraformaldehyde

“…[19] The yields of the macrocycles proved to be slightly less than those of isomers 1a,b. [17,19] The methyl group is introduced either at the C 5 atom or at the C 6 atom of the pyrimidine ring to permit or to prohibit any electrophilic substitution at the C 5 position. As a result, the reaction of pyrimidinophanes 1e,f with paraformaldehyde can occur only with 6-methyluracil but not with the thymine fragments of the compounds, whereas in macrocycles 1c,d both 6-methyluracil moieties can react with paraformaldehyde to afford methylene bridges connecting the C 5 atoms of the pyrimidine rings.…”

“…As excellent starting monomeric pyrimidinophanes for their cross-linking into multipyrimidinophanes, we considered isomeric pyrimidinophanes 1a,b previously developed [17,19] and distinguished from one another by mutual arrangement, trans (pyrimidinophanes 1a) or cis (pyrimidinophanes 1b) to the C 4 =O groups at the pyrimidine cycles, as shown in Figure 1. It was assumed that reaction of one or both uracil moieties in isomers 1a,b with paraformaldehyde might afford linearly arranged multipyrimidinophanes 2a,b, which are schematically represented in Figure 2.…”

“…Pyrimidinophanes are of interest in connection with the stacking structures in DNA, the formation of pyrimidine photodimers in DNA by ultraviolet light, [12] the mechanistic studies on DNA photolysis, [13] complexation properties, [14,15] and biological activity. [16][17][18] A series of pyrimidinophanes with three [9] and four uracil fragments [10] was prepared by ring-closing acid-catalyzed reaction of 1,3-bis[ω-(N-methyluracil-1-yl)alkyl]-thymines and α,β-bis(3,6-dimethyl-uracil-1-yl)alkanes with paraformaldehyde in the presence of copper(I) chloride.…”

Synthesis of 5-hetaryluracil derivatives via 1,3-dipolar cycloaddition reaction

“…After a few minutes the suspension disappeared and then white solid started to precipitate from a solution. The stirring was continued for 24 h. The solid was filtered off and purified on silica gel column using a mixture of CHCl 3 …”

“…The solid consisting of a mixture of two isomeric oximes was isolated in yield of 93% (0.34 g). The E/Z isomers were separated on silica gel column using MeOH : CHCl 3 18 (s, 3H, N1-CH 3 ), 3.38 (s, 3H, N3-CH 3 ), 7.86 (s, 1H, H-6), 8.09 (s, 1H, CH=N), 11.06 (s, 5, 36.7, 104.7, 141.1, 141.4, 150.9, 161.4 Methyl 3-(5-((hydroxyimino)methyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate (7b). A solution of AcONa*3H 2 O (1.63 g, 12 mmol) and NH 2 OH*HCl (0.97 g, 14 mmol) in H 2 O (10 mL) was added while stirring to a suspension of 6 (2.29 g, 10 mmol) in EtOH (20 mL).…”