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

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 con...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2012-07, Vol.75 (7), p.1414-1418
Main Authors: Priestap, Horacio A, Barbieri, Manuel A, Johnson, Francis
Format: Article
Language:English
Subjects:
Aristolochic Acids - chemistry
Carboxylic Acids - chemistry
DNA Adducts
Molecular Structure
Naphthalenes - chemistry
Oxazoles - chemistry
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np300137f