Remarkably fast and selective aromatization of Hantzsch esters with MoOCl4 and MoCl5: a chemical model for possible biologically relevant properties of molybdenum-containing enzymes

Bioorg Med Chem Lett. 2012 Jun 1;22(11):3676-81. doi: 10.1016/j.bmcl.2012.04.043. Epub 2012 Apr 13.

Abstract

Mo(VI) and Mo(V) salts both react selectively with Hantzsch esters to produce substitute pyridines in good-to-excellent yield (75-99%). The remarkable reactivity and selectivity of MoOCl(4) under reflux of acetonitrile and MoCl(5) in dichloromethane at room temperature encouraged us to propose that molybdenum-containing enzymes (such as xanthine or aldehyde oxidase) also participate to some degree in the metabolism of 1,4-dihydropyridine drugs in the liver analogous to NADH in the respiratory chain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehyde Oxidase / metabolism*
  • Chlorides / chemistry*
  • Dihydropyridines / chemistry
  • Dihydropyridines / metabolism
  • Esters
  • Models, Chemical
  • Molybdenum / chemistry*
  • Xanthine Oxidase / metabolism*

Substances

  • Chlorides
  • Dihydropyridines
  • Esters
  • 1,4-dihydropyridine
  • Molybdenum
  • molybdenum chloride
  • Xanthine Oxidase
  • Aldehyde Oxidase