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 Sep 21 |
| Externally published | Yes |
ASJC Scopus subject areas
- Pharmacology
- Pharmaceutical Science
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Inoue, K., Ohe, T., Mori, K., Sagara, T., Ishii, Y., & Chiba, M. (2009). Aromatic substitution reaction of 2-chloropyridines catalyzed by microsomal glutathione S-transferase 1. Drug Metabolism and Disposition, 37(9), 1797-1800. https://doi.org/10.1124/dmd.109.027698