Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas
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2017-09-01
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Universidade Federal de Goiás
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The chalcones are key intermediates for the biosynthesis of flavonoids and have shown an
abundance of pharmacological effects including the antitumor effect. Thus, the synthesis and
characterization of several chalcones and derivatives become important to develop a new class of
compounds having antitumor activity. In the present work, the synthesis of chalcones,
nitrochalcone sulfonamides and quinolinones was performed. By adjusting the reaction time and
the sequence of the reactions, hybrids of open-chain chalcone sulfonamide whose molecular
hybridization occurred at the ortho position of the benzoyl chalcone group through the Claisen-
Schmidt condensation of acetophenone sulfonamide and nitrobenzaldehyde can be obtained at
shorter reaction times, whereas quinolinone from cyclization at β carbon can be achieved if the
reaction is stopped sequentially later. It is also noted that a novel structure, a chalcone (bis)
sulfonamide, was prepared when chalcone was first synthesized and then reacted with
benzenesulfonyl chloride. From the sulfonamide chalcones prepared with the m-
aminoacetophenone sulfonamide and the o-, m- and p-nitrobenzaldehyde, a single product was
formed. Among the 21 compounds prepared, five were ketone sulfonamides and sixteen were
hybrid compounds (chalcones, chalcones, sulfonamides and quinolinones), which were purified
by extraction, recrystallization and column chromatography and characterized by small molecule
crystallography, melting point, Proton Nuclear Magnetic Resonance ( 1 H NMR) and infrared IV
(IR). The antitumor activity was evaluated against three cancer cell lines: SF-295 (human
glioblastoma), PC-3 (prostate) and HCT-116 (colon). Compounds 39, 40, 42, 43, 45a, 48a, 48b,
48c, 49 and 51 were cytotoxic to the three tumor cell lines tested. However, the quinolinones
showed no relevant cytotoxic effect. It is also worth noting that compound 45a with a higher
cytotoxic effect than doxorubicin, a drug used today against the three cancer cell lines evaluated,
was a promising prototype for a new drug.
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CASTRO, M. R. C. Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas. 2017. 206 f. Tese (Doutorado em Química) - Universidade Federal de Goiás, Goiânia, 2017.