Synthesis and Mutagenicity of Dihydrodiol Metabolites of Benzo[b] fluoranthene

Shantu Amin, Nalband Hussain, Harry Brielmann, Stephen S. Hecht

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The syntheses of the two major hepatic microsomal dihydrodiol metabolites of the environmental carcinogen, benzo[5]fluoranthene, are described. 1, 2-Dihydro-1, 2-dihydroxybenzo [5]fluoranthene was prepared from 11Hbenzo[b] fluorene-11-carboxylic acid. The key intermediate was l-oxo-1, 2, 3, 3a-tetrahydrobenzo[b]fluoranthene which was prepared by regiospecific cyclization of 1lR-benzo [b]fluorene-11-propionic acid chloride. 11, 12-Dihydro-11, 12-dihydroxybenzo[6]fluoranthene was synthesized from 2-methylfluoranthene via 12-oxo-9, 10, 11, 12-tetrahydrobenzo[b]fluoranthene. Both dihydrodiols were mutagenic toward Salmonella typhimurium 100, but their activities were less than that of benzo[b] fluoranthene.

Original languageEnglish (US)
Pages (from-to)1091-1095
Number of pages5
JournalJournal of Organic Chemistry
Volume49
Issue number6
DOIs
StatePublished - Mar 1984

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Metabolites
Environmental Carcinogens
Salmonella
Cyclization
Carboxylic Acids
Chlorides
trans-1,2-dihydro-1,2-naphthalenediol
benzo(b)fluoranthene
fluoranthene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Amin, Shantu ; Hussain, Nalband ; Brielmann, Harry ; Hecht, Stephen S. / Synthesis and Mutagenicity of Dihydrodiol Metabolites of Benzo[b] fluoranthene. In: Journal of Organic Chemistry. 1984 ; Vol. 49, No. 6. pp. 1091-1095.
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abstract = "The syntheses of the two major hepatic microsomal dihydrodiol metabolites of the environmental carcinogen, benzo[5]fluoranthene, are described. 1, 2-Dihydro-1, 2-dihydroxybenzo [5]fluoranthene was prepared from 11Hbenzo[b] fluorene-11-carboxylic acid. The key intermediate was l-oxo-1, 2, 3, 3a-tetrahydrobenzo[b]fluoranthene which was prepared by regiospecific cyclization of 1lR-benzo [b]fluorene-11-propionic acid chloride. 11, 12-Dihydro-11, 12-dihydroxybenzo[6]fluoranthene was synthesized from 2-methylfluoranthene via 12-oxo-9, 10, 11, 12-tetrahydrobenzo[b]fluoranthene. Both dihydrodiols were mutagenic toward Salmonella typhimurium 100, but their activities were less than that of benzo[b] fluoranthene.",
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Synthesis and Mutagenicity of Dihydrodiol Metabolites of Benzo[b] fluoranthene. / Amin, Shantu; Hussain, Nalband; Brielmann, Harry; Hecht, Stephen S.

In: Journal of Organic Chemistry, Vol. 49, No. 6, 03.1984, p. 1091-1095.

Research output: Contribution to journalArticle

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T1 - Synthesis and Mutagenicity of Dihydrodiol Metabolites of Benzo[b] fluoranthene

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AB - The syntheses of the two major hepatic microsomal dihydrodiol metabolites of the environmental carcinogen, benzo[5]fluoranthene, are described. 1, 2-Dihydro-1, 2-dihydroxybenzo [5]fluoranthene was prepared from 11Hbenzo[b] fluorene-11-carboxylic acid. The key intermediate was l-oxo-1, 2, 3, 3a-tetrahydrobenzo[b]fluoranthene which was prepared by regiospecific cyclization of 1lR-benzo [b]fluorene-11-propionic acid chloride. 11, 12-Dihydro-11, 12-dihydroxybenzo[6]fluoranthene was synthesized from 2-methylfluoranthene via 12-oxo-9, 10, 11, 12-tetrahydrobenzo[b]fluoranthene. Both dihydrodiols were mutagenic toward Salmonella typhimurium 100, but their activities were less than that of benzo[b] fluoranthene.

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