SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES

The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (S E Ar) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis...

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Autores principales:	OSORIO,MAURICIO E, QUIROZ,KAROL A, CARVAJAL,MARCELA A, VERGARA,ALEJANDRA P, SÁNCHEZ,ELIZABETH Y, GONZÁLEZ,CESAR E, CATALÁN,KAREN S
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2016
Materias:	C-prenylation prenylated acetophenone prenylated benzaldehyde electrophilic aromatic substitution anti-phytopathogenic DPPH radical scavenging activity
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072016000300018
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spelling	oai:scielo:S0717-970720160003000182017-06-14SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDESOSORIO,MAURICIO EQUIROZ,KAROL ACARVAJAL,MARCELA AVERGARA,ALEJANDRA PSÁNCHEZ,ELIZABETH YGONZÁLEZ,CESAR ECATALÁN,KAREN S C-prenylation prenylated acetophenone prenylated benzaldehyde electrophilic aromatic substitution anti-phytopathogenic DPPH radical scavenging activity The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (S E Ar) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay and expressed as half maximal inhibitory concentration (IC50) values in μΜ concentrations. The antioxidant activity went from 27.20 μΜ to >100 μΜ. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC50 values between 250 and <3.9 μΜ.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.61 n.3 20162016-09-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072016000300018en10.4067/S0717-97072016000300018
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	C-prenylation prenylated acetophenone prenylated benzaldehyde electrophilic aromatic substitution anti-phytopathogenic DPPH radical scavenging activity
spellingShingle	C-prenylation prenylated acetophenone prenylated benzaldehyde electrophilic aromatic substitution anti-phytopathogenic DPPH radical scavenging activity OSORIO,MAURICIO E QUIROZ,KAROL A CARVAJAL,MARCELA A VERGARA,ALEJANDRA P SÁNCHEZ,ELIZABETH Y GONZÁLEZ,CESAR E CATALÁN,KAREN S SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES
description	The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (S E Ar) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay and expressed as half maximal inhibitory concentration (IC50) values in μΜ concentrations. The antioxidant activity went from 27.20 μΜ to >100 μΜ. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC50 values between 250 and <3.9 μΜ.
author	OSORIO,MAURICIO E QUIROZ,KAROL A CARVAJAL,MARCELA A VERGARA,ALEJANDRA P SÁNCHEZ,ELIZABETH Y GONZÁLEZ,CESAR E CATALÁN,KAREN S
author_facet	OSORIO,MAURICIO E QUIROZ,KAROL A CARVAJAL,MARCELA A VERGARA,ALEJANDRA P SÁNCHEZ,ELIZABETH Y GONZÁLEZ,CESAR E CATALÁN,KAREN S
author_sort	OSORIO,MAURICIO E
title	SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES
title_short	SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES
title_full	SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES
title_fullStr	SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES
title_full_unstemmed	SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES
title_sort	synthesis, anti-phytopathogenic and dpph radical scavenging activities of c-prenylated acetophenones and benzaldehydes
publisher	Sociedad Chilena de Química
publishDate	2016
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072016000300018
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SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES

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