A facile synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid: Metabolite of anti-hyperlipidemic drug Fenofibrate

Synthesis and characterization of drug metabolites has emerged as an important area of research in consideration to the significant contribution of studies on metabolites in drug research. The present work comprises synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid,...

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Main Authors: Greesha N Majethia, Wahajul Haq, Ganesaratnam K. Balendiran
Format: Article
Language:English
Published: Elsevier 2024-01-01
Series:Results in Chemistry
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2211715623005210
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author Greesha N Majethia
Wahajul Haq
Ganesaratnam K. Balendiran
author_facet Greesha N Majethia
Wahajul Haq
Ganesaratnam K. Balendiran
author_sort Greesha N Majethia
collection DOAJ
description Synthesis and characterization of drug metabolites has emerged as an important area of research in consideration to the significant contribution of studies on metabolites in drug research. The present work comprises synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid, a metabolite of anti-hyperlipidemic drug fenofibrate. The desired compound was prepared by two different synthetic routes. The ketone group of fenofibric acid was reduced using sodium borohydride in one route whereas the hydrolysis of isopropyl ester of the reduced fenofibrate was achieved by the mild alkaline hydrolysis in the other path. Both the ways of synthesis furnished the desired compound in excellent yield and purity. The new synthetic congener was characterized by spectroscopic methods.
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spelling doaj.art-bdf26fa0e5f045cb8576b58d4dedc9812024-01-03T04:12:30ZengElsevierResults in Chemistry2211-71562024-01-017101282A facile synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid: Metabolite of anti-hyperlipidemic drug FenofibrateGreesha N Majethia0Wahajul Haq1Ganesaratnam K. Balendiran2Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, OH, USADepartment of Chemistry, Youngstown State University, One University Plaza, Youngstown, OH, USACorresponding author.; Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, OH, USASynthesis and characterization of drug metabolites has emerged as an important area of research in consideration to the significant contribution of studies on metabolites in drug research. The present work comprises synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid, a metabolite of anti-hyperlipidemic drug fenofibrate. The desired compound was prepared by two different synthetic routes. The ketone group of fenofibric acid was reduced using sodium borohydride in one route whereas the hydrolysis of isopropyl ester of the reduced fenofibrate was achieved by the mild alkaline hydrolysis in the other path. Both the ways of synthesis furnished the desired compound in excellent yield and purity. The new synthetic congener was characterized by spectroscopic methods.http://www.sciencedirect.com/science/article/pii/S2211715623005210FenofibrateSynthetic metabolitesAlkaline hydrolysisSodium borohydride reduction
spellingShingle Greesha N Majethia
Wahajul Haq
Ganesaratnam K. Balendiran
A facile synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid: Metabolite of anti-hyperlipidemic drug Fenofibrate
Results in Chemistry
Fenofibrate
Synthetic metabolites
Alkaline hydrolysis
Sodium borohydride reduction
title A facile synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid: Metabolite of anti-hyperlipidemic drug Fenofibrate
title_full A facile synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid: Metabolite of anti-hyperlipidemic drug Fenofibrate
title_fullStr A facile synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid: Metabolite of anti-hyperlipidemic drug Fenofibrate
title_full_unstemmed A facile synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid: Metabolite of anti-hyperlipidemic drug Fenofibrate
title_short A facile synthesis of 2-(4-((4-chlorophenyl)(hydroxy)methyl) phenoxy)-2-methylpropanoic acid: Metabolite of anti-hyperlipidemic drug Fenofibrate
title_sort facile synthesis of 2 4 4 chlorophenyl hydroxy methyl phenoxy 2 methylpropanoic acid metabolite of anti hyperlipidemic drug fenofibrate
topic Fenofibrate
Synthetic metabolites
Alkaline hydrolysis
Sodium borohydride reduction
url http://www.sciencedirect.com/science/article/pii/S2211715623005210
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