Síntesis de ácidos n-fenil y n-bencilantranílicos mediante reacción de Ullmann y evaluación de su actividad antioxidante e inhibidora de acetilcolinesterasa.

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Title:	Síntesis de ácidos n-fenil y n-bencilantranílicos mediante reacción de Ullmann y evaluación de su actividad antioxidante e inhibidora de acetilcolinesterasa.
Authors:	Rojas-Ruiz, Fernando A.¹, Merchan-Arenas, Diego R.¹, Pellón-Comdom, Rolando F.² rolando.pellon@infomed.sld.cu, Kouznetsov, Vladimir V.¹
Source:	Revista CENIC Ciencias Quimicas. 2010, Vol. 41 Issue 2, p123-129. 7p.
Subjects:	CHEMICAL synthesis, BENZOATES, SOLVENTS, CONDENSATION reactions, CHEMISTRY experiments, ANTIOXIDANTS
Abstract (English):	ABSTRACT. The reaction of 2-halogen benzoic acids with amines using copper salts or metal as catalyst in order to obtain N-phenylanthranilic acids is known as the Ullmann condensation. Several alcohols have been satisfactorily used as solvents in this reaction of which the most commonly used is isoamyl alcohol. Other solvents of higher boiling points like dimethylformamide are usually employed when high temperatures are required. However, the harsh reaction conditions and the use of contaminant solvents, led to severe limitations in the general use of this reaction, especially in the synthesis of bioactive products on a large scale. Although the use of water as a solvent in the reaction, was a step forward, this procedure sometimes leads to long heating times due to the high heat capacity of water. In the present work, N-phenyl and N-benzylantranilic acids were synthesized by modified Ullmann reaction. Modifications consisted in use of PEG 400 as innocuous solvent. Furthermore, the antioxidant and AChE inhibition activities of the panel of molecules obtained were evaluated, showing a potential antioxidant capacity relative to Trolox with TEAC values between 0,81 and 2,0 and a moderated AChE inhibition with IC50 between 12.26 and 28.62 ug/mL . [ABSTRACT FROM AUTHOR]
Abstract (Spanish):	La reacción de un ácido 2-halogenobenzoico con aminas usando sales de cobre o cobre metálico como catalizador para obtener ácidos N-fenilantranílicos se conoce como la reacción de condensación de Ullmann. Se han empleado satisfactoriamente como disolventes varios alcoholes en esta reacción, de los cuales el más comúnmente usado es el alcohol isoamílico. Otros disolventes de elevado punto de ebullición como la dimetilformamida son empleados usualmente cuando se requiere de elevadas temperaturas. Sin embargo, las duras condiciones de reacción y el uso de disolventes contaminantes, llevan a severas limitaciones en el uso general de esta reacción, especialmente, en la síntesis de productos bioactivos en gran escala. Aunque el empelo del agua como disolvente en la reacción, fue un paso de avance, este procedimiento lleva en ocasiones, a largos tiempos de calentamiento debido a la capacidad calórica del agua. En el presente trabajo, se sintetizaron ácidos N-fenil y N-bencilantranílicos mediante reacción de Ullmann modificada con rendimientos entre 55 y 90 %. Las modificaciones consistieron en el uso de PEG 400 como disolvente inocuo. Además, por primera vez se evaluó la actividad antioxidante e inhibidora de AChE del panel de moléculas obtenidas y se observó una potencial capacidad antioxidante relativa al Trolox con valores de TEAC entre 0,81 y 2,0 y una actividad moderada de inhibición de AChE de IC50 entre 12,26 y 28,62 ug/mL [ABSTRACT FROM AUTHOR]
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Database:	MedicLatina

Description
Abstract:	ABSTRACT. The reaction of 2-halogen benzoic acids with amines using copper salts or metal as catalyst in order to obtain N-phenylanthranilic acids is known as the Ullmann condensation. Several alcohols have been satisfactorily used as solvents in this reaction of which the most commonly used is isoamyl alcohol. Other solvents of higher boiling points like dimethylformamide are usually employed when high temperatures are required. However, the harsh reaction conditions and the use of contaminant solvents, led to severe limitations in the general use of this reaction, especially in the synthesis of bioactive products on a large scale. Although the use of water as a solvent in the reaction, was a step forward, this procedure sometimes leads to long heating times due to the high heat capacity of water. In the present work, N-phenyl and N-benzylantranilic acids were synthesized by modified Ullmann reaction. Modifications consisted in use of PEG 400 as innocuous solvent. Furthermore, the antioxidant and AChE inhibition activities of the panel of molecules obtained were evaluated, showing a potential antioxidant capacity relative to Trolox with TEAC values between 0,81 and 2,0 and a moderated AChE inhibition with IC50 between 12.26 and 28.62 ug/mL . [ABSTRACT FROM AUTHOR]
ISSN:	10158553