2026-05-21T23:11:39Zhttps://repisalud.isciii.es/rest/oai/requestoai:repisalud.isciii.es:20.500.12105/161132025-06-17T08:46:24Zcom_20.500.12105_2052com_20.500.12105_2051col_20.500.12105_19616
Repisalud
author
Martín-Acosta, Pedro
author
Cuadrado, Irene
author
González-Cofrade, Laura
author
Pestano, Roberto
author
Hortelano, Sonsoles
author
de Las Heras, Beatriz
author
Estévez-Braun, Ana
funder
Ministerio de Ciencia e Innovación (España)
funder
Agencia Canaria de Investigación, Innovación y Sociedad de la Información
funder
Unión Europea. Fondo Europeo de Desarrollo Regional (FEDER/ERDF)
funder
Instituto de Salud Carlos III
2023-05-24T07:58:51Z
2023-05-24T07:58:51Z
2023-02-24
J Nat Prod. 2023 Feb 24;86(2):317-329.
10.1021/acs.jnatprod.2c00924
1520-6025
Journal of natural products
36749898
http://hdl.handle.net/20.500.12105/16113
A set of new dihydroquinoline embelin derivatives was obtained from the reaction of the natural benzoquinone embelin (1) with anilines and aromatic aldehydes in the presence of AgOTf. The synthesis of these compounds involves the formation of a Knoevenagel adduct, followed by nucleophilic addition of aniline and subsequent electrocyclic ring closure. The scope of the reaction regarding the aldehydes and anilines was determined. Quinoline derivatives were also obtained from the corresponding dihydroquinolines under oxidation with DDQ. The cardioprotective activity of the synthesized compounds was screened using a doxorubicin-induced cardiotoxicity model in H9c2 cardiomyocytes. Some structure-activity relationships were outlined, and the best activities were achieved with quinoline-embelin derivatives having a 4-nitrophenyl group attached at the pyridine ring. The obtained results indicated that embelin derivatives 4i, 6a, 6d, 6k, and 6m could have potential as cardioprotective agents, as they attenuated a DOX-induced cardiotoxicity effect acting on oxidative stress and apoptosis.
eng
Synthesis of Quinoline and Dihydroquinoline Embelin Derivatives as Cardioprotective Agents
research article
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SynthesisQuinolineDihydroquinolineEmbelin_2023.pdf
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https://repisalud.isciii.es/bitstreams/57e02111-4bd1-48be-bf8f-d22a8042acd2/download
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SynthesisQuinolineDihydroquinolineEmbelin_2023.pdf.txt