Furanchalcone–biphenyl hybrids: synthesis, in silico studies, antitrypanosomal and cytotoxic activities
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Other documents of the author: García, Elisa; Ochoa, Rodrigo; Vasquez, Isabel; Conesa Milián, Laura; Carda, Miguel; Yepes, Andrés; Vélez, Iván D.; Robledo, Sara M.; Cardona Galeano, Wilson Isidro
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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Title
Furanchalcone–biphenyl hybrids: synthesis, in silico studies, antitrypanosomal and cytotoxic activitiesAuthor (s)
Date
2019Publisher
Springer VerlagISSN
1054-2523; 1554-8120Bibliographic citation
García, E., Ochoa, R., Vásquez, I. et al. Med Chem Res (2019) 28: 608. https://doi.org/10.1007/s00044-019-02323-7Type
info:eu-repo/semantics/articlePublisher version
https://link.springer.com/article/10.1007/s00044-019-02323-7Version
info:eu-repo/semantics/acceptedVersionSubject
Abstract
The synthesis, antitrypanosomal, and cytotoxic activities of 17 furanchalcone derivatives are described herein. The structure
of the synthesized products was elucidated by a combination of spectrometric analyses. The ... [+]
The synthesis, antitrypanosomal, and cytotoxic activities of 17 furanchalcone derivatives are described herein. The structure
of the synthesized products was elucidated by a combination of spectrometric analyses. The synthesized compounds were
evaluated against Trypanosoma cruzi, which is the pathogenic species to humans. Cytotoxicity was evaluated against human
U-937 macrophages. Eleven compounds were active against amastigotes of T. cruzi with EC50 values lower than 40 µM.
Hybrids 7b–7d and 8a–8g showed better activity than benznidazole. Structure activity relationship (SAR) showed that the
presence of electron withdrawing groups, such as nitro or fluorine, increased the activity and that the degree of oxygenation
is essential for activity. In addition, molecular docking was used to identify a possible protein target for the designed
compounds. A spearman correlation of 0.608 between the predicted scores and the experimental data profile the enzyme
cruzipain as a potential candidate. Finally, in silico ADMET studies of the arylfuranchalcones showed that these novel
compounds have suitable drug-like properties, making them potentially promising agents for antichagasic therapy. [-]
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Medicinal Chemistry Research (2019) 28Investigation project
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“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: https://doi.org/10.1007/s00044-019-02323-7”
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