Biomimetic oxidation of 2-methylimidazole derivative with a chemical model system for cytochrome P-450

Hiroyuki Miyachi, Yoshio Nagatsu

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A chemical model system for cytochrome P-450, consisting of tetraphenylporphyrin manganese chloride (TPPMnCl) and iodosylbenzene, efficiently oxidized 2-methylimidazole to 2-methylimidazolone. This system next applied to 4-(2-methyl-1-imidazolyl)-2,2-diphenylbutyramide, a muscarinic acetylcholine receptor antagonist under clinical trial, affording the previously unisolated imidazole ring 5-mono-oxidized derivative that considered to be the precursor of the main metabolites. This system, which is superior to the copper-ascorbate system, should be applicable to in vitro studies of various drugs containing the 2-methylimidazole moiety.

Original languageEnglish
Pages (from-to)1137-1140
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume50
Issue number8
DOIs
Publication statusPublished - Aug 2002
Externally publishedYes

Fingerprint

Chemical Models
Biomimetics
Cytochrome P-450 Enzyme System
Derivatives
Oxidation
Cholinergic Antagonists
Muscarinic Receptors
Metabolites
Copper
Clinical Trials
Pharmaceutical Preparations
2-methylimidazole
tetraphenylporphyrin
imidazole
In Vitro Techniques
manganese chloride
iodosobenzene

Keywords

  • 2-methylimidazole derivative
  • 2-methylimidazolone derivative
  • Drug metabolism
  • Metabolic intermediate
  • Metalloporphyrin
  • P-450 Chemical model

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Biomimetic oxidation of 2-methylimidazole derivative with a chemical model system for cytochrome P-450. / Miyachi, Hiroyuki; Nagatsu, Yoshio.

In: Chemical and Pharmaceutical Bulletin, Vol. 50, No. 8, 08.2002, p. 1137-1140.

Research output: Contribution to journalArticle

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