Aromatic substitution reaction of 2-chloropyridines catalyzed by microsomal glutathione S-transferase 1

Kazuko Inoue, Tomoyuki Ohe, Kenichi Mori, Takeshi Sagara, Yasuyuki Ishii, Masato Chiba

Research output: Contribution to journalArticle

14 Citations (Scopus)

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 languageEnglish
Pages (from-to)1797-1800
Number of pages4
JournalDrug Metabolism and Disposition
Volume37
Issue number9
DOIs
Publication statusPublished - 2009
Externally publishedYes

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Glutathione
Chlorine
Electrons
Liver
microsomal glutathione S-transferase-I
2-chloropyridine

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 journalArticle

Inoue, Kazuko ; Ohe, Tomoyuki ; Mori, Kenichi ; Sagara, Takeshi ; Ishii, Yasuyuki ; Chiba, Masato. / Aromatic substitution reaction of 2-chloropyridines catalyzed by microsomal glutathione S-transferase 1. In: Drug Metabolism and Disposition. 2009 ; Vol. 37, No. 9. pp. 1797-1800.
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