Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas
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2019-06-07
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Universidade Federal de Goiás
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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two are unpublished, and the structural elucidation by means of the crystallography of one of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 The data of the unpublished molecule were obtained by X-ray diffraction of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.
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FERREIRA, L. O. A. Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas. 2019. 64 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Goiânia, 2019.