RESUMO
Three series of d-galactose derivatives linked to a lipophilic aminoalcohol moiety were synthesized and their antibacterial activity was evaluated against Mycobacterium tuberculosis and representative species of Gram positive and Gram negative bacteria. Five out of the thirteen tested compounds displayed activity against M. tuberculosis, with a minimal inhibitory concentration (MIC) of 12.5 µg/mL and seven compounds were active against the four bacterial strains tested. The best results were obtained for amino alcohols 10 and 11 against Staphylococcus epidermidis (MIC = 2 µg/mL). The antitumor activity was evaluated against three tumor cell lines (MCF-7, HeLa and MO59J) and compared to the normal cell line GM07492A. The results showed that the lowest IC50 values were observed for the amino alcohol 16 against MCF-7 (11.9 µM) and MO59J (10.0 µM).
Assuntos
Amino Álcoois/farmacologia , Antibacterianos/farmacologia , Antineoplásicos/farmacologia , Amino Álcoois/síntese química , Amino Álcoois/química , Antibacterianos/síntese química , Antibacterianos/química , Antineoplásicos/síntese química , Antineoplásicos/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
In this study, Raman, infrared, UV/vis, NMR, and single crystal X-ray diffraction spectroscopies are used to elucidate the tautomeric equilibrium of azo dyes derived from 1-phenyl-azo-2-naphthol (Sudan I). A new crystallographic structure is described for Sudan I, revealing the presence of intramolecular hydrogen bonds and supramolecular interactions, such as the unconventional C-H···O hydrogen bond type, π-stacking, and charge-dipole interactions. All of these weak intermolecular interactions play a role in the stability of the crystalline structure. Theoretical calculations are also reported for geometries, energy, and spectroscopic properties. The predicted spectra are in accordance with the experiments carried out in the solid state and in solution of dichloromethane, carbon tetrachloride, and chloroform, suggesting the hydrazo form as the preferable tautomer in gas and condensate phases for Sudan I and its derivatives.
Assuntos
Compostos Azo/química , Corantes/química , Naftóis/química , Cristalografia por Raios X , Ligação de Hidrogênio , Modelos Moleculares , Estrutura Molecular , Teoria QuânticaRESUMO
Density functional theory (DFT) calculations of (1) H NMR chemical shifts for l-quebrachitol isomers were performed using the B3LYP functional employing the 6-31G(d,p) and 6-311 + G(2d,p) basis sets. The effect of the solvent on the B3LYP-calculated NMR spectrum was accounted for using the polarizable continuum model. Comparison is made with experimental (1) H NMR spectroscopic data, which shed light on the average uncertainty present in DFT calculations of chemical shifts and showed that the best match between experimental and theoretical B3LYP (1) H NMR profiles is a good strategy to assign the molecular structure present in the sample handled in the experimental measurements. Among four plausible O-methyl-inositol isomers, the l-quebrachitol 2a structure was unambiguously assigned based only on the comparative analysis of experimental and theoretical (1) H NMR chemical shift data. The B3LYP infrared (IR) spectrum was also calculated for the four isomers and compared with the experimental data, with analysis of the theoretical IR profiles corroborating assignment of the 2a structure. Therefore, it is confirmed in this study that a combined experimental/DFT spectroscopic investigation is a powerful tool in structural/conformational analysis studies.
Assuntos
Inositol/análogos & derivados , Teoria Quântica , Configuração de Carboidratos , Inositol/química , Espectroscopia de Ressonância Magnética/normas , Prótons , Padrões de Referência , EstereoisomerismoRESUMO
Two synthetic epoxide derivatives, important intermediates in organic synthesis, were obtained from L-quebrachitol, and their conformations were proposed based on spectroscopic analysis. Density functional theory (DFT) calculations of infrared and NMR spectra were shown to be reliable enough for organic chemistry applications. The observed structures were determined with the aid of the DFT spectroscopic data, stressing the relevance and utility of combined experimental/theoretical studies and also the usefulness of the (13)C NMR B3LYP/6-31G(d,p) calculations.