Artículo
Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study
Zígolo, María Antonela
; Salinas, Franco Maximiliano
; Alche, Laura Edith
; Garcia Liñares, Guadalupe Eugenia
; Baldessari, Alicia
Fecha de publicación:
08/2018
Editorial:
Academic Press Inc Elsevier Science
Revista:
Bioorganic Chemistry
ISSN:
0045-2068
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
We present an efficient approach to the synthesis of a series of glycyrrhetinic acid derivatives. Six derivatives, five of them new compounds, were obtained through chemoenzymatic reactions in very good to excellent yield. In order to find the optimal reaction conditions, the influence of various parameters such as enzyme source, nucleophile:substrate ratio, enzyme:substrate ratio, solvent and temperature was studied. The excellent results obtained by lipase catalysis made the procedure very efficient considering their advantages such as mild reaction conditions and low environmental impact. Moreover, in order to explain the reactivity of glycyrrhetinic acid and the acetylated derivative to different nucleophiles in the enzymatic reactions, molecular docking studies were carried out. In addition, one of the synthesized compounds exhibited remarkable antiviral activity against TK + and TK- strains of Herpes simplex virus type 1 (HSV-1), sensitive and resistant to acyclovir (ACV) treatment.
Palabras clave:
Glycyrrhetinic acid
,
Lypase-catalyzed
,
Molecular modeling
,
Antivirals
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Articulos(INIQUI)
Articulos de INST.DE INVEST.PARA LA INDUSTRIA QUIMICA (I)
Articulos de INST.DE INVEST.PARA LA INDUSTRIA QUIMICA (I)
Articulos(IQUIBICEN)
Articulos de INSTITUTO DE QUIMICA BIOLOGICA DE LA FACULTAD DE CS. EXACTAS Y NATURALES
Articulos de INSTITUTO DE QUIMICA BIOLOGICA DE LA FACULTAD DE CS. EXACTAS Y NATURALES
Articulos(UMYMFOR)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)
Citación
Zígolo, María Antonela; Salinas, Franco Maximiliano; Alche, Laura Edith; Garcia Liñares, Guadalupe Eugenia; Baldessari, Alicia; Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study; Academic Press Inc Elsevier Science; Bioorganic Chemistry; 78; 8-2018; 210-219
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