SYNTHESIS AND IN VITRO AND IN VIVO LEISHMANICIDAL EVALUATION OF BUTHEIN AND ITS DERIVATIVES
Chalcones, butein, Claisen-Schmidt condensation, prenylation
This study aimed to synthesize methoxylated derivatives and new
prenylated/methoxyprenylated derivatives of butein. Intermediates were synthesized
such as 2-hydroxy-4-methoxyacetophenone and 2,4-dimethoxyacetophenone, followed by
synthesis of chalcones, including buteine, homobuteine, 4'-methoxybutein, 3,4'-
dimethoxybutein and 3,4,4'-trimethoxybutein. The synthesis was carried out in an acidic medium,
using SOCl₂/EtOH as catalyst, with yields varying between 62% and
75%. The compounds were characterized by 1 H NMR spectroscopy and
13 C, and the melting points were compared with literature data. The results
indicated that Claisen-Schmidt condensation in an acidic medium was effective for
synthesis of chalcones, except for the trimethoxylated one, which required a
alternative. Despite the yields obtained being lower than expected, the
synthesized compounds showed structures consistent with the data
spectroscopic and melting point measurements reported in the literature.