Synthesis and mutagenicity of trans-dihydrodiol metabolites of benzo(b)naphtho(2,1-d)thiophene
- American Health Foundation, Valhalla, NY (USA)
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 NaBH{sub 4} 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 a 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.
- OSTI ID:
- 6411491
- Journal Information:
- Chemical Research in Toxicology; (USA), Journal Name: Chemical Research in Toxicology; (USA) Vol. 3:2; ISSN CRTOE; ISSN 0893-228X
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
CARCINOGENS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
METABOLIC ACTIVATION
METABOLITES
MUTAGEN SCREENING
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
POLYCYCLIC AROMATIC HYDROCARBONS
SCREENING
SPECTRA
SYNTHESIS
THIOPHENE