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

被引:0
作者
Majethia, Greesha N. [1 ]
Haq, Wahajul [1 ]
Balendiran, Ganesaratnam K. [1 ]
机构
[1] Youngstown State Univ, Dept Chem, One Univ Plaza, Youngstown, OH 44455 USA
关键词
Fenofibrate; Synthetic metabolites; Alkaline hydrolysis; Sodium borohydride reduction; HDL-CHOLESTEROL;
D O I
10.1016/j.rechem.2023.101282
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页数:5
相关论文
共 42 条
[1]   Late-Stage Formal Double C-H Oxidation of Prenylated Molecules to Alkylidene Oxetanes and Azetidines by Strain-Enabled Cross-Metathesis [J].
Albitz, Krisztian ;
Csokas, Daniel ;
Dobi, Zoltan ;
Papai, Imre ;
Soos, Tibor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (13)
[2]   Metabolomics approach reveals effects of antihypertensives and lipid-lowering drugs on the human metabolism [J].
Altmaier, Elisabeth ;
Fobo, Gisela ;
Heier, Margit ;
Thorand, Barbara ;
Meisinger, Christine ;
Roemisch-Margl, Werner ;
Waldenberger, Melanie ;
Gieger, Christian ;
Illig, Thomas ;
Adamski, Jerzy ;
Suhre, Karsten ;
Kastenmueller, Gabi .
EUROPEAN JOURNAL OF EPIDEMIOLOGY, 2014, 29 (05) :325-336
[3]   Metabolism and toxicity of drugs. Two decades of progress in industrial drug metabolism [J].
Baillie, Thomas A. .
CHEMICAL RESEARCH IN TOXICOLOGY, 2008, 21 (01) :129-137
[4]  
Balendiran G.K., 2004, In Search of Aldose Reductase Inhibitors, V12, P276
[5]  
Balendiran Ganesaratnam K, 2007, Curr Chem Biol, V1, P311, DOI 10.2174/187231307781662198
[6]   Fibrates inhibit aldose reductase activity in the forward and reverse reactions [J].
Balendiran, GK ;
Rajkumar, B .
BIOCHEMICAL PHARMACOLOGY, 2005, 70 (11) :1653-1663
[7]   A new insight into the treatment of diabetes by means of pan PPAR agonists [J].
Chandra, Avik ;
Kaur, Paranjeet ;
Sahu, Sanjeev Kumar ;
Mittal, Amit .
CHEMICAL BIOLOGY & DRUG DESIGN, 2022, 100 (06) :947-967
[8]   Development of Fibrates as Important Scaffolds in Medicinal Chemistry [J].
Giampietro, Letizia ;
Ammazzalorso, Alessandra ;
Amoroso, Rosa ;
De Filippis, Barbara .
CHEMMEDCHEM, 2019, 14 (11) :1051-1066
[9]   Selective Synthesis of the Human Drug Metabolite 5′-Hydroxypropranolol by an Evolved Self-Sufficient Peroxygenase [J].
Gomez de Santos, Patricia ;
Canellas, Marina ;
Tieves, Florian ;
Younes, Sabry H. H. ;
Molina-Espeja, Patricia ;
Hofrichter, Martin ;
Hollmann, Frank ;
Guallar, Victor ;
Alcalde, Miguel .
ACS CATALYSIS, 2018, 8 (06) :4789-4799
[10]   Micronized fenofibrate: A new fibric acid hypolipidemic agent [J].
Guay, DRP .
ANNALS OF PHARMACOTHERAPY, 1999, 33 (10) :1083-1103