Synthesis of potential drug metabolites by a modified Udenfriend reaction

The scope and the limitations of a modified Udenfriend reaction for the one-step synthesis of potential drug metabolites were explored. Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions (Fe 2+/Mn 2+/EDTA/asco...

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Published inTetrahedron letters Vol. 52; no. 7; pp. 749 - 752
Main Authors Slavik, Roger, Peters, Jens-Uwe, Giger, Rudolf, Bürkler, Markus, Bald, Eric
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.02.2011
Elsevier
Subjects
Accessibility
Aromatic hydroxylation
Biomedical materials
Biomimetic oxidation
chemical structure
Chemistry
Chemistry, Organic
chlorpromazine
derivatization
Diltiazem
Drug discovery
Drugs
hydroxylation
In vivo testing
In vivo tests
Metabolites
oxidation
Physical Sciences
propranolol
Science & Technology
Synthesis (chemistry)
Aromatic hydroxylation
Drug discovery
Metabolites
Biomimetic oxidation
CLOZAPINE
RAT
DEMETHYLATION
MIST
HYDROGEN-PEROXIDE
FENTON REAGENT
MODEL
SELECTIVITY
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Abstract The scope and the limitations of a modified Udenfriend reaction for the one-step synthesis of potential drug metabolites were explored. Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions (Fe 2+/Mn 2+/EDTA/ascorbic acid/O 2). From each reaction, one to four oxidation products were obtained in 1–8% overall yield. Many of these products (9 out of 14) have been reported to be metabolites of the parent drugs in vivo. The products resulted mainly from aromatic hydroxylation, and are not readily accessible by conventional synthesis. Thus, the described reaction may be useful in drug discovery whenever a facile synthetic access is more important than high yields (e.g., for a fast derivatisation of compounds or the preparation of metabolites). Poorly water-soluble compounds cannot be converted, which is an important limitation of this method.
AbstractList Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions (Fe²⁺/Mn²⁺/EDTA/ascorbic acid/O₂). From each reaction, one to four oxidation products were obtained in 1–8% overall yield. Many of these products (9 out of 14) have been reported to be metabolites of the parent drugs in vivo. The products resulted mainly from aromatic hydroxylation, and are not readily accessible by conventional synthesis. Thus, the described reaction may be useful in drug discovery whenever a facile synthetic access is more important than high yields (e.g., for a fast derivatisation of compounds or the preparation of metabolites). Poorly water-soluble compounds cannot be converted, which is an important limitation of this method.
The scope and the limitations of a modified Udenfriend reaction for the one-step synthesis of potential drug metabolites were explored. Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions (Fe 2+/Mn 2+/EDTA/ascorbic acid/O 2). From each reaction, one to four oxidation products were obtained in 1–8% overall yield. Many of these products (9 out of 14) have been reported to be metabolites of the parent drugs in vivo. The products resulted mainly from aromatic hydroxylation, and are not readily accessible by conventional synthesis. Thus, the described reaction may be useful in drug discovery whenever a facile synthetic access is more important than high yields (e.g., for a fast derivatisation of compounds or the preparation of metabolites). Poorly water-soluble compounds cannot be converted, which is an important limitation of this method.
Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions (Fe2+/Mn2+/EDTA/ascorbic acid/O-2). From each reaction, one to four oxidation products were obtained in 1-8% overall yield. Many of these products (9 out of 14) have been reported to be metabolites of the parent drugs in vivo. The products resulted mainly from aromatic hydroxylation, and are not readily accessible by conventional synthesis. Thus, the described reaction may be useful in drug discovery whenever a facile synthetic access is more important than high yields (e.g., for a fast derivatisation of compounds or the preparation of metabolites). Poorly water-soluble compounds cannot be converted, which is an important limitation of this method. (C) 2010 Elsevier Ltd. All rights reserved.
Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions (Fe super(2+)/Mn super(2+)/EDTA/ascorbic acid/O sub(2)). From each reaction, one to four oxidation products were obtained in 1-8% overall yield. Many of these products (9 out of 14) have been reported to be metabolites of the parent drugs in vivo. The products resulted mainly from aromatic hydroxylation, and are not readily accessible by conventional synthesis. Thus, the described reaction may be useful in drug discovery whenever a facile synthetic access is more important than high yields (e.g., for a fast derivatisation of compounds or the preparation of metabolites). Poorly water-soluble compounds cannot be converted, which is an important limitation of this method.
Author Slavik, Roger
Peters, Jens-Uwe
Bürkler, Markus
Giger, Rudolf
Bald, Eric
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Keywords Aromatic hydroxylation
Drug discovery
Metabolites
Biomimetic oxidation
CLOZAPINE
RAT
DEMETHYLATION
MIST
HYDROGEN-PEROXIDE
FENTON REAGENT
MODEL
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Snippet The scope and the limitations of a modified Udenfriend reaction for the one-step synthesis of potential drug metabolites were explored. Several drugs...
Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions...
Several drugs (clozapine, chlorpromazine, imipramine, buspirone, diltiazem, and propranolol) were subjected to modified Udenfriend conditions (Fe super(2+)/Mn...
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SubjectTerms Accessibility
Aromatic hydroxylation
Biomedical materials
Biomimetic oxidation
chemical structure
Chemistry
Chemistry, Organic
chlorpromazine
derivatization
Diltiazem
Drug discovery
Drugs
hydroxylation
In vivo testing
In vivo tests
Metabolites
oxidation
Physical Sciences
propranolol
Science & Technology
Synthesis (chemistry)
Title Synthesis of potential drug metabolites by a modified Udenfriend reaction
URI https://dx.doi.org/10.1016/j.tetlet.2010.12.014
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