Universidad Peruana Cayetano Heredia

Trypanocidal properties, structure-activity relationship and computational studies of quinoxaline 1,4-di-N-oxide derivatives

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dc.contributor.author Estevez, Y.
dc.contributor.author Quiliano, M.
dc.contributor.author Burguete, A.
dc.contributor.author Cabanillas Amado, Billy Joel
dc.contributor.author Zimic-Peralta, Mirko Juan
dc.contributor.author Málaga, E.
dc.contributor.author Verastegui Pimentel, Manuela Renee
dc.contributor.author Pérez-Silanes, S.
dc.contributor.author Aldana, I.
dc.contributor.author Monge, A.
dc.contributor.author Castillo Pareja, Denis Helan
dc.contributor.author Deharo, E.
dc.date.accessioned 2022-01-18T19:26:46Z
dc.date.available 2022-01-18T19:26:46Z
dc.date.issued 2011
dc.identifier.uri https://hdl.handle.net/20.500.12866/10853
dc.description.abstract Pyrazole and propenone quinoxaline derivatives were tested against intracellular forms of Leishmania peruviana and Trypanosoma cruzi. Both series were tested for toxicity against proliferative and non-proliferative cells. The pyrazole quinoxaline series was quite inactive against T. cruzi; however, the compound 2,6-dimethyl-3-f-quinoxaline 1,4-dioxide was found to inhibit 50% of Leishmania growth at 8.9 μM, with no impact against proliferative kidney cells and with low toxicity against THP-1 cells and murine macrophages. The compounds belonging to the propenone quinoxaline series were moderately active against T. cruzi. Among these compounds, two were particularly interesting, (2E)-1-(7-fluoro-3-methyl-quinoxalin-2-yl)-3-(3,4,5-trimethoxy-phenyl)-propenone and (2E)-3-(3,4,5-trimethoxy-phenyl)-1-(3,6,7-trimethyl-quinoxalin-2-yl)-propenone. The former possessed selective activity against proliferative cells (cancer and parasites) and was inactive against murine peritoneal macrophages; the latter was active against Leishmania and inactive against the other tested cells. Furthermore, in silico studies showed that both series respected Lipinski’s rules and that they confirmed a linear correlation between trypanocidal activities and LogP. Docking studies revealed that compounds of the second series could interact with the poly (ADP-ribose) polymerase protein of Trypanosoma cruzi. en_US
dc.language.iso eng
dc.publisher Elsevier
dc.relation.ispartofseries Experimental Parasitology
dc.rights info:eu-repo/semantics/restrictedAccess
dc.rights.uri https://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
dc.subject Female en_US
dc.subject article en_US
dc.subject controlled study en_US
dc.subject animal cell en_US
dc.subject Animals en_US
dc.subject Mice en_US
dc.subject mouse en_US
dc.subject non|priority journal en_US
dc.subject unclassified drug en_US
dc.subject Trypanocidal Agents en_US
dc.subject human cell en_US
dc.subject Trypanosoma cruzi en_US
dc.subject Leishmania en_US
dc.subject protozoal protein en_US
dc.subject Leishmania peruviana en_US
dc.subject correlation analysis en_US
dc.subject cell proliferation en_US
dc.subject amphotericin B en_US
dc.subject Mice, Inbred BALB C en_US
dc.subject Molecular Structure en_US
dc.subject Structure-Activity Relationship en_US
dc.subject drug synthesis en_US
dc.subject growth inhibition en_US
dc.subject Murinae en_US
dc.subject antiprotozoal activity en_US
dc.subject antitrypanosomal agent en_US
dc.subject drug cytotoxicity en_US
dc.subject Quinoxalines en_US
dc.subject molecular docking en_US
dc.subject Cercopithecus aethiops en_US
dc.subject drug selectivity en_US
dc.subject Vero Cells en_US
dc.subject kidney cell en_US
dc.subject computer model en_US
dc.subject drug protein binding en_US
dc.subject Macrophages, Peritoneal en_US
dc.subject 1 (7 fluoro 3 methyl quinoxalin 2 yl) 3 (3,4,5 trimethoxyphenyl)propenone en_US
dc.subject 2,6 dimethyl 3 f quinoxaline 1,4 dioxide en_US
dc.subject 3 (3,4,5 trimethoxyphenyl) 1 (3,6,7 trimethyl quinoxalin 2 yl)propenone en_US
dc.subject mathematical computing en_US
dc.subject nicotinamide adenine dinucleotide adenosine diphosphate ribosyltransferase en_US
dc.subject peritoneum macrophage en_US
dc.subject quinoxaline 1,4 oxide derivative en_US
dc.subject Quinoxaline 1,4-di-N-oxide derivatives en_US
dc.subject trimethoxyphenyl propenone en_US
dc.subject trimethoxyphenyl pyrazole quinoxaline en_US
dc.title Trypanocidal properties, structure-activity relationship and computational studies of quinoxaline 1,4-di-N-oxide derivatives en_US
dc.type info:eu-repo/semantics/article
dc.identifier.doi https://doi.org/10.1016/j.exppara.2011.01.009
dc.subject.ocde https://purl.org/pe-repo/ocde/ford#3.03.07
dc.relation.issn 1090-2449


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