title: 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.
abstract: 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.
authors: Department of Biological Sciences, Florida International University , 11200 Southwest 8th Street, Miami, Florida 33199, USA. priestap@fiu.edu
authors: Horacio A
authors: HA
authors: Priestap
authors: Manuel A
authors: MA
authors: Barbieri
authors: Francis
authors: F
authors: Johnson
mesh_terms: D034341:Aristolochic Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D018736:DNA Adducts; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*
chemical_list: C575785:2-methylnaphtho(1,2-d)oxazole-9-carboxylic acid; C575786:8-nitro-1-naphthoic acid; D034341:Aristolochic Acids; D002264:Carboxylic Acids; D018736:DNA Adducts; D009281:Naphthalenes; D010080:Oxazoles; C555177:aristoxazole; C000228:aristolochic acid I