Enterococcus faecalis is known as a significant nosocomial pathogen due to its natural resistance to many antibacterial drugs. Moreover, it was found that E. faecalis infection causes inflammation, production of reactive oxygen species, and DNA damage to human gastric cancer cells, which can induce cancer. In this study, we synthesized and tested the biological activity of a new Schiff base, 5-[(4-ethoxyphenyl)imino]methyl-N-(4-fluorophenyl)-6-methyl-2-phenylpyrimidin-4-amine (3), and compared its properties with an analogous amine (2). In the biological investigation, (3) was found to have antibacterial activity against E. faecalis 29212 and far better anticancer properties, especially against gastric adenocarcinoma (human Caucasian gastric adenocarcinoma), than (2). In addition, both derivatives were non-toxic to normal cells. It is worth mentioning that (3) could potentially inhibit cancer cell growth by inducing cell apoptosis. The results suggest that the presence of the –C=N– bond in the molecule of (3) increases its activity, indicating that 5-iminomethylpyrimidine could be a potent core for further drug discovery research.

The paper presents the synthesis of 5-substituted pyrimidine sulphonamides as well as the results of studies on the antibacterial and antifungal activity of obtained derivatives.

Fused pyrimidine derivativesFused pyrimidine derivatives R 0515Synthesis and Antibacterial Properties of Pyrimidopyrimidines. -Fourteen new pyrimidopyrimidines are prepared and microbially tested on 10 bacterial strains. Derivatives exhibit particular significant antibacterial effects if the phenyl ring contains a highly electronegative substituent. In these cases, the activity is comparable with sulfacarbamide and some of them have even stronger bacterial growth inhibitors than presently used antibiotics erythromycin. -(CIEPLIK*, J.; PLUTA, J.; GUBRYNOWICZ, O.; Sci. Pharm. 70 (2002) 3, 245-252; Dep. Org. Chem., Med. Acad., PL-50-137 Wroclaw, Pol.; Eng.) -Bartels 04-153

This article presents the synthesis of three new 4-thiopyrimidine derivatives obtained from ethyl 4-methyl-2-phenyl-6-sulfanylpyrimidine-5-carboxylate as the starting material, namely, ethyl 4-[(4-chlorobenzyl)sulfanyl]-6-methyl-2phenylpyrimidine-5-carboxylate, C 21 H 19 ClN 2 O 2 S, (2), {4-[(4-chlorobenzyl)sulfanyl]-6-methyl-2-phenylpyrimidin-5-yl}methanol, C 19 H 17 ClN 2 OS, (3), and 4-[(4-chlorobenzyl)sulfanyl]-5,6-dimethyl-2-phenylpyrimidine, C 19 H 17 ClN 2 S, (4), which vary in the substituent at the 5-position of the pyrimidine ring. The compounds were characterized by 1 H NMR, 13 C NMR, IR and mass spectroscopies, and also elemental analysis. The molecular structures were further studied by single-crystal X-ray diffraction. Compound (2) crystallizes in the space group P1 with one molecule in the asymmetric unit, whereas compounds (3) and (4) crystallize in the space group P2 1 /c with two and one molecule, respectively, in their asymmetric units. The conformation of each molecule is best defined by the dihedral angles formed between the pyrimidine ring and the planes of the two aryl substituents attached at the 2-and 4-positions. The only structural difference between the three compounds is the substituent at the 5-position of the pyrimidine ring, but they present significantly different features in the hydrogenbond interactions. Compound (2) displays a one-dimensional chain formed by hydrogen bonds and the chains are further extended into a two-dimensional network. Molecules of (3) and (4) generate one-dimensional chains formed through intermolecular interactions. The study examines the cytotoxicity of compounds (3) and (4) against Human umbilical vein endothelial cells (HUVEC) and HeLa, K562 and CFPAC cancer cell lines. The presence of the hydroxymethyl and methyl groups in (3) and (4), respectively, offers an interesting new insight into the structures and behaviour of these derivatives. Compound (4) was found to be nontoxic against CFPAC and HUVEC; however, it shows weak activity against the HeLa and K563 cell lines. The presence of a hydroxy group in (3) significantly increases its cytotoxicity towards both, i.e. the cancer (HeLa, K562 and CFPAC) and normal (HUVEC) cell lines.

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