Abstract
We investigated the substitution reaction of a series of 2-chloropyridine derivatives catalyzed by rat liver microsomal glutathione S-transferase 1. Various 2-chloropyridine derivatives were metabolized to the corresponding substituted glutathione conjugates via displacement of chlorine atom with glutathione. The reaction was affected by the electron-withdrawing strength and position of the substituents. Molecular orbital calculations on the change in Gibbs free energy between the initial and transition states verified the presence of a Meisenheimer complex and its influence on the reaction rate.
| Original language | English |
|---|---|
| Pages (from-to) | 1797-1800 |
| Number of pages | 4 |
| Journal | Drug Metabolism and Disposition |
| Volume | 37 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2009 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Pharmacology
- Pharmaceutical Science
Cite this
Aromatic substitution reaction of 2-chloropyridines catalyzed by microsomal glutathione S-transferase 1. / Inoue, Kazuko; Ohe, Tomoyuki; Mori, Kenichi; Sagara, Takeshi; Ishii, Yasuyuki; Chiba, Masato.
In: Drug Metabolism and Disposition, Vol. 37, No. 9, 2009, p. 1797-1800.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Aromatic substitution reaction of 2-chloropyridines catalyzed by microsomal glutathione S-transferase 1
AU - Inoue, Kazuko
AU - Ohe, Tomoyuki
AU - Mori, Kenichi
AU - Sagara, Takeshi
AU - Ishii, Yasuyuki
AU - Chiba, Masato
PY - 2009
Y1 - 2009
N2 - We investigated the substitution reaction of a series of 2-chloropyridine derivatives catalyzed by rat liver microsomal glutathione S-transferase 1. Various 2-chloropyridine derivatives were metabolized to the corresponding substituted glutathione conjugates via displacement of chlorine atom with glutathione. The reaction was affected by the electron-withdrawing strength and position of the substituents. Molecular orbital calculations on the change in Gibbs free energy between the initial and transition states verified the presence of a Meisenheimer complex and its influence on the reaction rate.
AB - We investigated the substitution reaction of a series of 2-chloropyridine derivatives catalyzed by rat liver microsomal glutathione S-transferase 1. Various 2-chloropyridine derivatives were metabolized to the corresponding substituted glutathione conjugates via displacement of chlorine atom with glutathione. The reaction was affected by the electron-withdrawing strength and position of the substituents. Molecular orbital calculations on the change in Gibbs free energy between the initial and transition states verified the presence of a Meisenheimer complex and its influence on the reaction rate.
UR - http://www.scopus.com/inward/record.url?scp=70349103000&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=70349103000&partnerID=8YFLogxK
U2 - 10.1124/dmd.109.027698
DO - 10.1124/dmd.109.027698
M3 - Article
C2 - 19541825
AN - SCOPUS:70349103000
VL - 37
SP - 1797
EP - 1800
JO - Drug Metabolism and Disposition
JF - Drug Metabolism and Disposition
SN - 0090-9556
IS - 9
ER -