Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4

AUTOR(ES)

Santos, Edson dos A. dos, Prado, Paulo C., Carvalho, Wanderley R. de, Lima, Ricardo V. de, Beatriz, Adilson, Lima, Dênis P. de, Hamel, Ernest, Dyba, Marzena A., Albuquerque, Sergio

FONTE

Quím. Nova

DATA DE PUBLICAÇÃO

2013

RESUMO

We extended our previous exploration of sulfur bridges as bioisosteric replacements for atoms forming the bridge between the aromatic rings of combretastatin A-4. Employing coupling reactions between 5-iodo-1,2,3-trimethoxybenzene and substituted thiols, followed by oxidation to sulfones with m-CPBA, different locations for attaching the sulfur atom to ring A through the synthesis of nine compounds were examined. Antitubulin activity was performed with electrophoretically homogenous bovine brain tubulin, and activity occurred with the 1,2,3-trimethoxy-4-[(4-methoxyphenyl)thio]benzene (12), while the other compounds were inactive. The compounds were also tested for leishmanicidal activity using promastigote forms of Leishmania braziliensis (MHOM/BR175/M2904), and the greatest activity was observed with 1,2,3-trimethoxy-4-(phenylthio)benzene (10) and 1,2,3-trimethoxy-4-[(4-methoxyphenyl) sulfinyl]benzene (15).

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