Synthesis, antiprotozoal activity and cytotoxicity in U-937 macrophages of triclosan–hydrazone hybrids
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Otros documentos de la autoría: Vergara, Sebastián; Carda, Miguel; Agut, Raúl; Yepes, Lina M.; Vélez, Iván D.; Robledo, Sara M.
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INVESTIGACIONMetadatos
Título
Synthesis, antiprotozoal activity and cytotoxicity in U-937 macrophages of triclosan–hydrazone hybridsAutoría
Fecha de publicación
2017Editor
Springer VerlagISSN
1054-2523; 1554-8120Cita bibliográfica
Vergara, S., Carda, M., Agut, R. et al. Med Chem Res (2017) 26: 3262. https://doi.org/10.1007/s00044-017-2019-2Tipo de documento
info:eu-repo/semantics/articleVersión de la editorial
https://link.springer.com/article/10.1007/s00044-017-2019-2Versión
info:eu-repo/semantics/acceptedVersionPalabras clave / Materias
Resumen
The synthesis and biological activities (cytotoxicity, leishmanicidal, and trypanocidal) of 11 triclosan–hydrazone hybrids are described herein. The structure of the products was elucidated by spectral data (NMR, IR) ... [+]
The synthesis and biological activities (cytotoxicity, leishmanicidal, and trypanocidal) of 11 triclosan–hydrazone hybrids are described herein. The structure of the products was elucidated by spectral data (NMR, IR) and mass spectrometric analyses. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis, which is the most prevalent Leishmania species in Colombia, and against Trypanosoma cruzi, which is the major pathogenic species to Chagas disease in humans. In addition, the cytotoxic activity of the synthesized compounds was evaluated against human U-937 macrophages. Hydrazone hybrids were obtained as E-synperiplanar and E-antiperiplanar conformers. Nine of them were active against L. (V) panamensis (5a–5d, 5f–5j) and eight of them against T. cruzi (5a, 5c, 5d, 5f–5j), with EC50 values lower than 40 µM. The compounds 5c, 5e, and 5h exhibit the best selectivity index against both L. (V) panamensis and T. cruzi, with values ranging from 5.90 to 16.55, thus showing potential as starting compounds for the eventual development of drugs against these parasites. The presence of hydroxy or methoxy groups in positions 2 and 4 of the aromatic ring of the benzylidene moiety increases both activity and cytotoxicity. There is no clear relationship between the antiprotozoal activity and the methylation pattern of the hydroxy groups, since in some cases methylation decreases the activity (5d vs. 5g) while in other cases the activity is increased (5c vs. 5f and 5i vs. 5j) [-]
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Med Chem Res (2017) 26Derechos de acceso
© Springer Science+Business Media, LLC 2017
“This is a post-peer-review, pre-copyedit version of an article published in Medicinal Chemistry Research. The final authenticated version is available online at: http://dx.doi.org/10.1007/s0004”.
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