Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas

Abstract

In the present work the synthesis, characterization of seven symmetric bischalcones, of which two are unpublished, and the structural elucidation by means of the crystallography of one of them, besides the cytotoxic analysis of all the compounds against 3 different lines of cancer. After synthesizing the compounds were characterized by 1 H Nuclear Magnetic Resonance (NMR), melting point, infrared (IR), Mass Spectrometry (MS) and elemental analysis of C and H (CHN). The compounds were obtained by the reaction of aldol condensation between the acetone and the benzaldehydes for substituted, in a yield of between 81.19 and 26.92%. The results of 1 H NMR, MS and CHN analyzes confirmed that the expected compounds were obtained in high purity. The crystallographic study was chosen as a technique to elucidate crystalline structure because it has been shown to be of fundamental importance to know the molecular arrangement and thus serving as an important tool for pharmacology and other related areas. The data of the unpublished molecule were obtained by X-ray diffraction of monocrystal, thus allowing to evaluate the geometric parameters, the distances and the interatomic angles, intermolecular interactions and the supramolecular arrangement. The selected crystal crystallized in the monoclinic system with four symmetry operations and a 50% disorder in two of its atoms, its interatomic distances and its binding angles were measured and compared with structures previously deposited in the Cambridge Crystallographic Data Center (CCDC). With the aid of 13 C solid-state nuclear magnetic resonance (NMR-s) and theoretical energy analysis, the presence of the mixed anti-syn confomer was detected. Considering the great advance in the studies of bischalcone and its potential tumor inhibitor, these compounds were sent to the Nucleus of Research and Development of Medicines (NRDM) of the Federal University of Ceará (UFC), with the purpose of evaluating its antitumor activity against the human cancer cells (SNB-19) (glioblastoma), PC-3 (prostate) and HCT-116 (colon), obtaining values of inhibition of growth in the 11% to 100%, and the ability to inhibit (IC 50 ) 50% of cell proliferation from 0.48 to 13.17 μg.ml -1 , the best compound being the 5.