Synthesis, Biological Evaluation and In Silico Computational Studies of 7‑Chloro-4-(1H‑1,2,3-triazol-1-yl)quinoline Derivatives: Search for New Controlling Agents against Spodoptera f rugiperda (Lepidoptera: Noctuidae) Larvae

dc.contributorhttp://orcid.org/0000-0003-4173-6826
dc.contributorhttp://orcid.org/0000-0003-1417-8355
dc.contributorhttps://orcid.org/0000-0003-4149-6623
dc.contributorhttps://orcid.org/0000-0003-4173-6826
dc.contributorhttps://scholar.google.es/citations?user=qj7XoWUAAAAJ&hl=es
dc.contributorhttps://scienti.minciencias.gov.co/cvlac/visualizador/generarCurriculoCv.do?cod_rh=0001363349
dc.contributorhttps://scienti.minciencias.gov.co/cvlac/visualizador/generarCurriculoCv.do?cod_rh=0000254410
dc.contributorhttps://scienti.minciencias.gov.co/cvlac/visualizador/generarCurriculoCv.do?cod_rh=0001351444
dc.creatorRosado-Solano, Doris Natalia
dc.creatorBaron-Rodríguez, Mario Alberto
dc.creatorSanabria Florez, Pedro Luis
dc.creatorLuna-Parada, Luz Karime
dc.creatorPuerto-Galvis, Carlos Eduardo
dc.creatorZorro-Gonzalez, Andres Felipe
dc.creatorKouznetsov, Vladimir V.
dc.creatorVargas-Mendez, Leonor Yamile
dc.date.accessioned2020-05-19T15:43:16Z
dc.date.accessioned2022-09-28T16:16:25Z
dc.date.available2020-05-19T15:43:16Z
dc.date.available2022-09-28T16:16:25Z
dc.date.created2020-05-19T15:43:16Z
dc.date.issued2020-05-18
dc.identifierhttp://hdl.handle.net/11634/23290
dc.identifierhttps://doi.org/10.1021/acs.jafc.9b01067
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/3679983
dc.description.abstractThe insecticidal and antifeedant activities of five 7-chloro-4-(1H-1,2,3-triazol-1-yl)quinoline derivatives were evaluated against the maize armyworm, Spodoptera f rugiperda (J.E. Smith). These hybrids were prepared through a coppercatalyzed azide alkyne cycloaddition (CuAAC, known as a click reaction) and displayed larvicidal properties with LD50 values below 3 mg/g insect, and triazolyl-quinoline hybrid 6 showed an LD50 of 0.65 mg/g insect, making it 2-fold less potent than methomyl, which was used as a reference insecticide (LD50 = 0.34 mg/g insect). Compound 4 was the most active antifeedant derivative (CE50 = 162.1 μg/mL) with a good antifeedant index (56−79%) at concentrations of 250−1000 μg/mL. Additionally, triazolyl-quinoline hybrids 4−8 exhibited weak inhibitory activity against commercial acetylcholinesterase from Electrophorus electricus (electric-eel AChE) (IC50 = 27.7 μg/mL) as well as low anti-ChE activity on S. f rugiperda larvae homogenate (IC50 = 68.4 μg/mL). Finally, molecular docking simulations suggested that hybrid 7 binds to the catalytic active site (CAS) of this enzyme and around the rim of the enzyme cavity, acting as a mixed (competitive and noncompetitive) inhibitor like methomyl. Triazolyl-quinolines 4−6 and 8 inhibit AChE by binding over the perimeter of the enzyme cavity, functioning as noncompetitive inhibitors. The results described in this work can help to identify lead triazole structures from click chemistry for the development of insecticide and deterrent products against S. f rugiperda and related insect pests
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dc.rightshttp://creativecommons.org/licenses/by-nc-nd/2.5/co/
dc.rightsAtribución-NoComercial-SinDerivadas 2.5 Colombia
dc.titleSynthesis, Biological Evaluation and In Silico Computational Studies of 7‑Chloro-4-(1H‑1,2,3-triazol-1-yl)quinoline Derivatives: Search for New Controlling Agents against Spodoptera f rugiperda (Lepidoptera: Noctuidae) Larvae
dc.typeGeneración de Nuevo Conocimiento: Artículos publicados en revistas especializadas - Electrónicos


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