SYNTHESIS AND BIOLOGICAL ACTIVITY OF SULFUR COMPOUNDS SHOWING STRUCTURAL ANALOGY WITH COMBRETASTATIN A-4

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 -CPBA,...

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Veröffentlicht in:Química Nova 2013-01, Vol.36 (2), p.279-283
Hauptverfasser: Dos Santos, Edson Dos A, Prado, Paulo C, de Carvalho, Wanderley R, de Lima, Ricardo V, Beatriz E, Adilson, de Lima, Dênis P, Hamel, Ernest, Dyba, Marzena A, Albuquerque, Sergio
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Sprache:eng
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Zusammenfassung: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 -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 ( ), 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 ( ) and 1,2,3-trimethoxy-4-[(4-methoxyphenyl) sulfinyl]benzene ( ).
ISSN:0100-4042
1678-7064
1678-7064
DOI:10.1590/S0100-40422013000200014