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. |
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| 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] |
| Copyright of Revista CENIC Ciencias Quimicas is the property of Centro Nacional de Investigaciones Cientificas and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | MedicLatina |
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| Items | – Name: Title Label: Title Group: Ti Data: Síntesis de ácidos n-fenil y n-bencilantranílicos mediante reacción de Ullmann y evaluación de su actividad antioxidante e inhibidora de acetilcolinesterasa. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Rojas-Ruiz%2C+Fernando+A%2E%22">Rojas-Ruiz, Fernando A.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Merchan-Arenas%2C+Diego+R%2E%22">Merchan-Arenas, Diego R.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Pellón-Comdom%2C+Rolando+F%2E%22">Pellón-Comdom, Rolando F.</searchLink><relatesTo>2</relatesTo><i> rolando.pellon@infomed.sld.cu</i><br /><searchLink fieldCode="AR" term="%22Kouznetsov%2C+Vladimir+V%2E%22">Kouznetsov, Vladimir V.</searchLink><relatesTo>1</relatesTo> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Revista+CENIC+Ciencias+Quimicas%22">Revista CENIC Ciencias Quimicas</searchLink>. 2010, Vol. 41 Issue 2, p123-129. 7p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22CHEMICAL+synthesis%22">CHEMICAL synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22BENZOATES%22">BENZOATES</searchLink><br /><searchLink fieldCode="DE" term="%22SOLVENTS%22">SOLVENTS</searchLink><br /><searchLink fieldCode="DE" term="%22CONDENSATION+reactions%22">CONDENSATION reactions</searchLink><br /><searchLink fieldCode="DE" term="%22CHEMISTRY+experiments%22">CHEMISTRY experiments</searchLink><br /><searchLink fieldCode="DE" term="%22ANTIOXIDANTS%22">ANTIOXIDANTS</searchLink> – Name: Abstract Label: Abstract (English) Group: Ab Data: 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] – Name: Abstract Label: Abstract (Spanish) Group: Ab Data: 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] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Revista CENIC Ciencias Quimicas is the property of Centro Nacional de Investigaciones Cientificas and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Languages: – Code: spa Text: Spanish PhysicalDescription: Pagination: PageCount: 7 StartPage: 123 Subjects: – SubjectFull: CHEMICAL synthesis Type: general – SubjectFull: BENZOATES Type: general – SubjectFull: SOLVENTS Type: general – SubjectFull: CONDENSATION reactions Type: general – SubjectFull: CHEMISTRY experiments Type: general – SubjectFull: ANTIOXIDANTS Type: general Titles: – TitleFull: Síntesis de ácidos n-fenil y n-bencilantranílicos mediante reacción de Ullmann y evaluación de su actividad antioxidante e inhibidora de acetilcolinesterasa. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Rojas-Ruiz, Fernando A. – PersonEntity: Name: NameFull: Merchan-Arenas, Diego R. – PersonEntity: Name: NameFull: Pellón-Comdom, Rolando F. – PersonEntity: Name: NameFull: Kouznetsov, Vladimir V. IsPartOfRelationships: – BibEntity: Dates: – D: 01 M: 08 Text: 2010 Type: published Y: 2010 Identifiers: – Type: issn-print Value: 10158553 Numbering: – Type: volume Value: 41 – Type: issue Value: 2 Titles: – TitleFull: Revista CENIC Ciencias Quimicas Type: main |
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