synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin a-4
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ID: 193952
2013
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Abstract
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).
| Reference Key |
santos2013qumicasynthesis
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| Authors | ;Edson dos A. dos Santos;Paulo C. Prado;Wanderley R. de Carvalho;Ricardo V. de Lima;Adilson Beatriz;Dênis P. de Lima;Ernest Hamel;Marzena A. Dyba;Sergio Albuquerque |
| Journal | greece and rome |
| Year | 2013 |
| DOI |
10.1590/S0100-40422013000200014
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