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Synthesis and Mutagenicity of Trans-Dihydrodiol Metabolites of benzo[b]naphtho[2,1-d]thiophene

Synthesis and Mutagenicity of Trans-Dihydrodiol Metabolites of benzo[b]naphtho[2,1-d]thiophene

B Misra, S Amin

Chem Res Toxicol. Mar-Apr 1990;3(2):93-7.

PMID: 1718470

Abstract:

The syntheses of potentially important metabolites of benzo[b]naphtho[2,1-d]thiophene ([2,1]BNT)--trans-1,2-dihydroxy-1,2-dihydrobenzo[b]naphtho[2,1- d]thiophene ([2,1]BNT-1,2-diol) and trans-3,4-dihydroxy-3,4-dihydrobenzo[b]naphtho[2,1-d]thiophene ([2,1]BNT-3,4-diol)--are described. The syntheses involved preparation of the appropriate 1-(3-benzo[b]-thiopheneyl)-2-(methoxyphenyl)ethylenes followed by photocyclization to methoxy-[2,1]BNTs, hydrolysis to hydroxy-[2,1]BNTs, oxidation to [2,1]BNT-diones, and NaBH4 reduction. The dihydrodiols were tested for mutagenicity in Salmonella typhimurium TA 100 with activation; [2,1]BNT-3,4-diol, which can form a bay region diol epoxide, was as mutagenic as [2,1]BNT whereas [2,1]BNT-1,2-diol was inactive. These results suggest that the metabolic activation of [2,1]BNT proceeds partially via formation of a bay region diol epoxide.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP205436	Benzo[b]naphtho[1,2-d]thiophene		205-43-6	Price

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