2014-09-082014-09-082011-08-17VALE, Joyce Karen Lima. Estudo do mecanismo do nitrofeniletano na prostaglandina-endoperóxido sintase e relação estrutura-propriedade de nitroderivados. 2011. 53 f. Dissertação (Mestrado) - Universidade Federal do Pará, Instituto de Ciências da Saúde, Belém, 2011. Programa de Pós-Graduação em Ciências Farmacêuticas.https://repositorio.ufpa.br/handle/2011/5620Previous studies suggest that the essential oil of Aniba canelilla containing high levels of 1-nitro-2-phenylethane has antinociceptive activity, anti-inflammatory and hypotensive. A theoretical study of correlation between chemical structure versus biological activity of 1-nitro-2-phenylethane and prostaglandin-endoperoxide synthase was performed. In addition, an analysis of the conformational nitrophenylethane as well as changes in their chemical structure resulting in cinnamates and nitrostyrenes derivatives, for further evaluation of structureproperty. The conformational analysis was performed using the nitrophenylethane DFT/B3LYP the method with the basis set 6-31G (d) by varying the twist angle between the links of dihedro carbons C1-C2 linked to the phenyl and nitro groups, ranging from 5 ° intervals in the range of 0° to 180° in order to search for the lowest energy conformers. The conformer of the 180° dihedron O2N-C6H5-C1-C2 was significantly more stable and this can be explained in terms of the balance by the presence of seven geometries of lower energies. The HOMO and LUMO analysis shows that the phenyl and methylene groups contribute to the formation of this orbital. The calculation of energy and determination of electronic properties related to the mechanism of interaction with the cyclooxygenase showed a high correlation between nitro and carboxylic groups, which can be classified as bioisosters. The results of physico-chemical calculations show a greater correlation of the nitrophenylethane with acetylsalicylic acid, which may have related to its mechanism of action through interactions with Arg-120 and Ser-530. Calculated with the protonated guanidine by DFT/B3LYP/6-31G (d, p) for the complex containing the carboxylate group exhibit more favorable interaction energy with a value of -136.34 kcal / mol, compared with the molecule containing the nitro group with a value of -12.84 kcal / mol, which may explain the greater effectiveness of indomethacin, similar to biological outcomes. Nitrophenylethane derivatives showed a structural relationship with cinnamates derived from differing in the redox properties, which may favor the development of prototype structures and bioactive molecules from these molecular skeletons.porAcesso AbertoÓleo aromáticoAniba canelillaCasca-preciosaNitrofeniletanoNitroderivadosAnálise físico-químicaDissertaçãoCNPQ::CIENCIAS DA SAUDE::FARMACIA::ANALISE E CONTROLE E MEDICAMENTOS