Estudo cristalográfico de isobenzofuran-1(3H)-onas com potencial atividade citotóxica

Detalhes bibliográficos
Ano de defesa: 2016
Autor(a) principal: Souza, Rafael Aparecido Carvalho
Orientador(a): Não Informado pela instituição
Banca de defesa: Não Informado pela instituição
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Uberlândia
Brasil
Programa de Pós-graduação em Química
Programa de Pós-Graduação: Não Informado pela instituição
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Palavras-chave em Português:
Link de acesso: https://repositorio.ufu.br/handle/123456789/17944
http://doi.org/10.14393/ufu.di.2016.415
Resumo: Heterocyclic compounds play an important role in various fields of scientific knowledge, including research and development of pharmaceuticals and agrochemicals. The isobezofuran-1(3H)-ones are biologically active with a wide range of pharmacological activities, including antiparasitic activity, cytotoxicity against cancer cell lines, antiplatelet drugs against cerebral ischemia apoplexy, among others. With the objective to obtain novel compounds and to evaluate the cytotoxic activity against tumor cell lines K562 (myeloid leukemia) and HL60 (leukemia), four isobezofuran-1(3H)-ones functionalized at the C-3 position were synthesized. In this work are shown the results of the structural elucidation by X–ray diffraction, of four novel organic compounds: Compound 1: 3-(2-phenyl-2-oxoethyl)-isobenzofuran-1(3H)-one; Compound 2: 3-[2-(4-methoxyphenyl)-2-oxoethyl)]-isobenzofuran-1(3H)-one; Compound 3: 3-[2-(4-hydroxyphenyl)-2-oxoethyl]-isobenzofuran-1(3H)-one; Compound 4: 3-[2-(4-methylphenyl)-2-oxoethyl]-isobenzofuran-1(3H)-one. The structures of the compounds 1-4 were elucidated. The results showed that compound 1 crystallize in the orthorhombic system, P212121 non-centrosymmetric space group and the other crystallizes in the monoclinic system in different centrosymmetric space groups. All compounds exhibit two substantially planar regions as follows: (1) isobenzofuranone ring and (2) 2-phenyl-2-oxoethyl. C3 atom of the isobenzofuranones is an asymmetric carbon. Compounds 2, 3 and 4 show in their crystal a racemic mixture (RS). Compound 1 doesn’t present racemic mixture and its absolute structure couldn’t be determined. In the crystal packing of the compounds 1 and 3 were found intramolecular interactions. The crystal of 1 has two intermolecular interactions: one C–H···O and one C–H···. The crystal of 3 presents three intermolecular interactions: one C–H···O, one C–H··· and a classical hydrogen bonding of the kind O–H···O. The crystal packing of the compounds 2 and 4 present one intramolecular interaction and five intermolecular interactions of the kind C– H···O and C–H···.