Synthesis and mutagenicity of trans-dihydrodiol metabolites of benzo[b]naphtho[2,1-d]thiophene

Bijay Misra, Shantu Amin

Research output: Contribution to journalArticle

20 Citations (Scopus)

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[6]naphtho[2,1-d]thiophene ([2,1]BNT-1,2-diol) and trans-3,4-dihydroxy-3,4-dihydrobenzo[6]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.

Original languageEnglish (US)
Pages (from-to)93-97
Number of pages5
JournalChemical Research in Toxicology
Volume3
Issue number2
DOIs
StatePublished - Jan 1 1990

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Metabolites
Thiophenes
Epoxy Compounds
Ethylenes
Chemical activation
trans-1,2-dihydro-1,2-naphthalenediol
benzo(b)naphtho(2,1-d)thiophene
Salmonella
Salmonella typhimurium
Hydrolysis
Oxidation

All Science Journal Classification (ASJC) codes

  • Toxicology

Cite this

@article{8ae041c3660d4af6a0a1a4ae38746fa3,
title = "Synthesis and mutagenicity of trans-dihydrodiol metabolites of benzo[b]naphtho[2,1-d]thiophene",
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[6]naphtho[2,1-d]thiophene ([2,1]BNT-1,2-diol) and trans-3,4-dihydroxy-3,4-dihydrobenzo[6]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.",
author = "Bijay Misra and Shantu Amin",
year = "1990",
month = "1",
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doi = "10.1021/tx00014a002",
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Synthesis and mutagenicity of trans-dihydrodiol metabolites of benzo[b]naphtho[2,1-d]thiophene. / Misra, Bijay; Amin, Shantu.

In: Chemical Research in Toxicology, Vol. 3, No. 2, 01.01.1990, p. 93-97.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and mutagenicity of trans-dihydrodiol metabolites of benzo[b]naphtho[2,1-d]thiophene

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N2 - The syntheses of potentially important metabolites of benzo[b]naphtho[2,1-d]thiophene ([2,1]BNT)—trans-1,2-dihydroxy-1,2-dihydrobenzo[6]naphtho[2,1-d]thiophene ([2,1]BNT-1,2-diol) and trans-3,4-dihydroxy-3,4-dihydrobenzo[6]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.

AB - The syntheses of potentially important metabolites of benzo[b]naphtho[2,1-d]thiophene ([2,1]BNT)—trans-1,2-dihydroxy-1,2-dihydrobenzo[6]naphtho[2,1-d]thiophene ([2,1]BNT-1,2-diol) and trans-3,4-dihydroxy-3,4-dihydrobenzo[6]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.

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