Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10637/11658
Título : Synthesis and biological studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and representative analogues : SAR studies
Autor : Hamulic, Damir.
Stadler, Marco.
Hering, Steffen.
Padrón Carrillo, José Manuel.
Bassett, Rachel.
Rivas, Fatima.
Loza Mejía, Marco Antonio.
Dea Ayuela, María Auxiliadora.
González Cardenete, Miguel Ángel.
Materias: Nuclear receptors (Biochemistry)Receptores nucleares (Bioquímica)Alkalies - Synthesis.Cells.Alcalis - Síntesis.Células.
Fecha de publicación : 6-mar-2019
Editorial : American Chemical Society and American Society of Pharmacognosy.
Citación : Hamulic, D., Stadler, M., Hering, S., Padrón, JM., Bassett, R., Rivas, F. et al. (2019). Synthesis and biological studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and representative analogues : SAR studies. Journal of Natural Products, vol. 82, n. 4 (6 mar.), pp. 823-831. DOI: https://doi.org/10.1021/acs.jnatprod.8b00884
Resumen : The first semisynthesis and biological profiling of the new abietane diterpenoid (+)-liquiditerpenoid acid (abietopinoic acid) (7) along with several analogues are reported. The compounds were obtained from readily available methyl dehydroabietate (8), which was derived from (−)-abietic acid (1). Biological comparison was conducted according to the different functional groups leading to some basic structure-activity relationship (SAR). In particular, the ferruginol and sugiol analogues 7 and 10-16, were characterized by the presence of an acetylated phenolic moiety, an oxidized C-7 as a carbonyl, and a different functional group at C-18 (methoxycarbonyl, carboxylic acid, and hydroxymethyl). The biological properties of these compounds were investigated against a panel of six representative human tumor solid cells (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), five leukemia cellular models (NALM-06, KOPN-8, SUP-B15, UoCB1, and BCR-ABL), and four Leishmania species (L. infantum, L. donovani, L. amazonensis, and L. guyanensis). A molecular docking study pointed out some targets in these Leishmania species. In addition, the ability of the compounds to modulate GABAA receptors (α1β2γ2s), is also reported. The combined findings indicate that these abietane diterpenoids offer a source of novel bioactive molecules with promising pharmacological properties from cheap chiral-pool building blocks.
Descripción : Este artículo se encuentra disponible en la página web de la revista en la siguiente URL: https://pubs.acs.org/doi/10.1021/acs.jnatprod.8b00884
Este es el pre-print del siguiente artículo: Hamulic, D., Stadler, M., Hering, S., Padrón, JM., Bassett, R., Rivas, F. et al. (2019). Synthesis and biological studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and representative analogues: SAR studies. Journal of Natural Products, vol. 82, i. 4, pp. 823-831, que se ha publicado de forma definitiva en https://doi.org/10.1021/acs.jnatprod.8b00884
This is the pre-peer reviewed version of the following article: Hamulic, D., Stadler, M., Hering, S., Padrón, JM., Bassett, R., Rivas, F. et al. (2019). Synthesis and biological studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and representative analogues: SAR studies. Journal of Natural Products, vol. 82, i. 4, pp. 823-831, which has been published in final form at https://doi.org/10.1021/acs.jnatprod.8b00884
URI : http://hdl.handle.net/10637/11658
Derechos: http://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
ISSN : 0163-3864
1520-6025 (Electrónico)
Aparece en las colecciones: Dpto. Farmacia

Ficheros en este ítem:
Fichero Descripción Tamaño Formato  
Synthesis_Hamulic_JNP_2019.pdf1,59 MBAdobe PDFVisualizar/Abrir



Los ítems de DSpace están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.