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dc.contributor.authorOtero, Elver
dc.contributor.authorRobledo, Sara M.
dc.contributor.authorDíaz Oltra, Santiago
dc.contributor.authorCarda, Miguel
dc.contributor.authorMuñoz, Diana
dc.contributor.authorPaños Pérez, Julián
dc.contributor.authorVélez, Iván D.
dc.contributor.authorCardona, Wilson
dc.date.accessioned2015-07-13T10:50:33Z
dc.date.available2015-07-13T10:50:33Z
dc.date.issued2014
dc.identifier.citationOTERO, Elver, et al. Synthesis and leishmanicidal activity of cinnamic acid esters: Structure–activity relationship. Medicinal Chemistry Research, 2014, vol. 23, no 3, p. 1378-1386.ca_CA
dc.identifier.issn1054-2523
dc.identifier.issn1554-8120
dc.identifier.urihttp://hdl.handle.net/10234/127408
dc.description.abstractSeveral cinnamic acid esters were obtained via Fischer esterification of cinnamic acids derivatives with aliphatic alcohols. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes and cytotoxic activity was evaluated against mammalian U-937 cells. The compounds 11, 15–17, and 23, were active against Leishmania parasite and although toxic for mammalian cells, they still are potential candidates for antileishmanial drug development. A SAR analysis indicates that first, while smaller alkyl chains lead to higher selectivity indices (10, 11 vs. 12–17); second, the degree of oxygenation is essential for activity, primarily in positions 3 and 4 (17 vs. 18–20 and 22); and third, hydroxyl groups increase both activity and cytotoxicity (14 vs. 23). On the other hand, the presence of a double bond in the side chain is crucial for cytotoxicity and leishmanicidal activity (12 vs. 21). However, further studies are required to optimize the structure of the promising molecules and to validate the in vitro activity against Leishmania demonstrated here with in vivo studies.ca_CA
dc.description.sponsorShipThe authors thank Dr. Javier Garcés for his help in this study. We acknowledge the support by the Universidad de Antioquia (Estrategia de Sostenibilidad 2013–2014 and CIDEPRO) and Colciencias (contract No. 357-2011).ca_CA
dc.format.extent9 p.ca_CA
dc.format.mimetypeapplication/pdfca_CA
dc.language.isoengca_CA
dc.publisherSpringerca_CA
dc.relation.isFormatOfSynthesis and leishmanicidal activity of cinnamic acid esters: Structure–activity relationship. Medicinal Chemistry Research, 2014, vol. 23, no 3, p. 1378-1386.ca_CA
dc.relation.isPartOfMedicinal Chemistry Research, 2014, vol. 23, no 3ca_CA
dc.rights© Springer International Publishing AG, Part of Springer Science+Business Mediaca_CA
dc.subjectleishmaniasisca_CA
dc.subjectantiprotozoalca_CA
dc.subjectcaffeic acidca_CA
dc.subjectcinnamic acid esterca_CA
dc.titleSynthesis and leishmanicidal activity of cinnamic acid esters: structure–activity relationshipca_CA
dc.typeinfo:eu-repo/semantics/articleca_CA
dc.identifier.doihttp://dx.doi.org/10.1007/s00044-013-0741-y
dc.rights.accessRightsinfo:eu-repo/semantics/openAccessca_CA
dc.relation.publisherVersionhttp://link.springer.com/article/10.1007%2Fs00044-013-0741-yca_CA


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