RESUMEN
Due to the increased resistance to antibiotics, in recent years there has been a growing interest in the discovery of new antimicrobial agents from different sources. Bacteria that are resistant to most antibiotics are a global public health concern. In order to find a new antimicrobial drug, we synthesized a small series of 2,4-diketo esters and tested them on some gram-positive and gram-negative bacterial strains. Two compounds showed very good antibacterial activity against Staphylococcus aureus and Bacillus subtilis, respectively. Trichophyton mentagrophytes proved to be the most sensitive of the tested species regarding antifungal activity. Also, research was conducted on the biomolecule of bovine serum albumin. Examining these interactions, we concluded that all compounds have the appropriate binding affinity for bovine serum albumin, which is vital. Furthermore, to investigate the potential antitumor activity, interactions with DNA were carried out. Examining the interactions between our compounds and DNA using fluorescence, we concluded that all but one of the compounds interacts with the DNA molecule by intercalation. In addition, a molecular docking study was performed to investigate the binding mode of the tested compounds to DNA and bovine serum albumin. In conclusion, all the results indicate a great potential for the future application of these compounds in clinical practice in the future.
Asunto(s)
Antiinfecciosos , Ésteres , Unión Proteica , Simulación del Acoplamiento Molecular , Ésteres/farmacología , Albúmina Sérica Bovina/química , Antibacterianos/química , ADN/química , Pruebas de Sensibilidad Microbiana , Bacterias GrampositivasRESUMEN
A small series of 1-acetyl-2-(4-alkoxy-3-methoxyphenyl)cyclopropanes was prepared, starting from dehydrozingerone (4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one) and its O-alkyl derivatives. Their microbiological activities toward some strains of bacteria and fungi were tested, as well as their in vitro cytotoxic activity against some cancer cell lines (HeLa, LS174 and A549). All synthesized compounds showed significant antimicrobial activity and expressed cytotoxic activity against tested carcinoma cell lines, but they showed no significant influence on normal cell line (MRC5). Butyl derivative is the most active on HeLa cells (IC50 = 8.63 µm), while benzyl one is active against LS174 and A549 cell lines (IC50 = 10.17 and 12.15 µm, respectively).
Asunto(s)
Antiinfecciosos/química , Estirenos/química , Células A549 , Antiinfecciosos/farmacología , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Cristalografía por Rayos X , Ciclopropanos/química , Ensayos de Selección de Medicamentos Antitumorales , Hongos/efectos de los fármacos , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Células HeLa , Humanos , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Relación Estructura-Actividad , Estirenos/toxicidadRESUMEN
A small library of novel 2-oxo-1,2,3,4-tetrahydropyrimidines was synthesized via a one-pot multicomponent Biginelli reaction. Copper complex [Formula: see text] which was used for the first time as a homogeneous and heterogeneous catalyst, makes this a facile and efficient reaction at room temperature. All the obtained products fall out of the solution in pure form and are easily isolated via filtration in good-to-excellent yields. The molecular structure of one of the products, ethyl 6-methyl-2-oxo-4-(4[Formula: see text]-isopropoxy-3[Formula: see text]-methoxyphenyl) - 1,2,3,4 - tetrahydropyrimidine-5- carboxylate, has been determined by X-ray crystallography. All non-hydrogen atoms in the heterocyclic, six-membered ring are determined to be approximately coplanar.
Asunto(s)
Aldehídos/química , Pirimidinas/síntesis química , Ácido Vanílico/química , Catálisis , Técnicas Químicas Combinatorias , Cristalografía por Rayos X , Estructura Molecular , Pirimidinas/químicaRESUMEN
In the title compound, C11H14OS, all non-H atoms are essentially coplanar, with a mean deviation of 0.023â Å. In the crystal, centrosymmetrically related mol-ecules are weakly connected into dimers by pairs of C-Hâ¯O inter-actions. The dimers are further linked along the a axis by weak C-Hâ¯π and C-Hâ¯S inter-actions.
RESUMEN
In the title compound, C10H12O3, all non-H atoms are approximately coplanar, with an r.m.s. deviation of 0.046â Å. In the crystal, very weak C-Hâ¯O inter-actions link the mol-ecules into sheets parallel to (101).