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 m-CPBA...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2013-01-01
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| Series: | Química Nova |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422013000200014 |
| _version_ | 1819100672613679104 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Edson dos A. dos Santos |
| collection | DOAJ |
| description | 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). |
| first_indexed | 2024-12-22T01:06:30Z |
| format | Article |
| id | doaj.art-675486a170604bd88fc5ebd7620c7406 |
| institution | Directory Open Access Journal |
| issn | 0100-4042 1678-7064 |
| language | English |
| last_indexed | 2024-12-22T01:06:30Z |
| publishDate | 2013-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Química Nova |
| spelling | doaj.art-675486a170604bd88fc5ebd7620c74062022-12-21T18:44:05ZengSociedade Brasileira de QuímicaQuímica Nova0100-40421678-70642013-01-01362279283Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4Edson dos A. dos SantosPaulo C. PradoWanderley R. de CarvalhoRicardo V. de LimaAdilson BeatrizDênis P. de LimaErnest HamelMarzena A. DybaSergio AlbuquerqueWe 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).http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422013000200014combretastatin A-4antitubulin activityleishmanicidal activity |
| spellingShingle | 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 Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4 Química Nova combretastatin A-4 antitubulin activity leishmanicidal activity |
| title | Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4 |
| title_full | Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4 |
| title_fullStr | Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4 |
| title_full_unstemmed | Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4 |
| title_short | Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4 |
| title_sort | synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin a 4 |
| topic | combretastatin A-4 antitubulin activity leishmanicidal activity |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422013000200014 |
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