Aristoxazole analogues. Conversion of 8-nitro-1-naphthoic acid to 2-methylnaphtho[1,2-d]oxazole-9-carboxylic acid: comments on the chemical mechanism of formation of DNA adducts by the aristolochic acids

J Nat Prod. 2012 Jul 27;75(7):1414-8. doi: 10.1021/np300137f. Epub 2012 Jul 2.


2-Methylnaphtho[1,2-d]oxazole-9-carboxylic acid was obtained by reduction of 8-nitro-1-naphthoic acid with zinc-acetic acid. This naphthoxazole is a condensation product between an 8-nitro-1-naphthoic acid reduction intermediate and acetic acid and is a lower homologue of aristoxazole, a similar condensation product of aristolochic acid I with acetic acid that was previously reported. Both oxazoles are believed to arise via a common nitrenium/carbocation ion mechanism that is likely related to that which leads to aristolochic acid-DNA-adducts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aristolochic Acids / chemistry*
  • Carboxylic Acids / chemistry*
  • DNA Adducts
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Oxazoles / chemistry*


  • 2-methylnaphtho(1,2-d)oxazole-9-carboxylic acid
  • 8-nitro-1-naphthoic acid
  • Aristolochic Acids
  • Carboxylic Acids
  • DNA Adducts
  • Naphthalenes
  • Oxazoles
  • aristoxazole
  • aristolochic acid I