Synthesis of k-region derivatives of the carcinogen 1-nitropyrene

Karam El-Bayoumy, Peter Villucci, Ajit K. Roy, Stephen S. Hecht

Research output: Contribution to journalArticle

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Abstract

The synthesis of potential metabolites of 1-nitropyrene, resulting from oxidation at the K-regions, is described. Reaction of 1-nitropyrene with OsO4 gave the cis-4, 5- and 9, 10-di-hydrodiols. These were separated and oxidized with activated MnO2 to give the corresponding 4, 5- and 9, 10-diones; further oxidation to the highly mutagenic lactones, 1- and 3-nitro-5H-phenanthro[4, 5-bed]pyran-5-one, was observed in these reactions. Reduction of the 4, 5-dione with KBH4 gave the trans-4, 5-dihydrodiol, which was identical to one of the metabolites of 1-nitropyrene. Reduction of the 9, 10-dione gave an unstable trans-9, 10-dihydrodiol, which was characterized as its diacetate. The u.v. spectra, n.m.r. spectra and h.p.l.c. retention times of these compounds are presented.

Original languageEnglish (US)
Pages (from-to)1577-1580
Number of pages4
JournalCarcinogenesis
Volume7
Issue number9
DOIs
StatePublished - Sep 1 1986

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1-nitropyrene
Carcinogens
Pyrans
Lactones

All Science Journal Classification (ASJC) codes

  • Cancer Research

Cite this

El-Bayoumy, Karam ; Villucci, Peter ; Roy, Ajit K. ; Hecht, Stephen S. / Synthesis of k-region derivatives of the carcinogen 1-nitropyrene. In: Carcinogenesis. 1986 ; Vol. 7, No. 9. pp. 1577-1580.
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Synthesis of k-region derivatives of the carcinogen 1-nitropyrene. / El-Bayoumy, Karam; Villucci, Peter; Roy, Ajit K.; Hecht, Stephen S.

In: Carcinogenesis, Vol. 7, No. 9, 01.09.1986, p. 1577-1580.

Research output: Contribution to journalArticle

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N2 - The synthesis of potential metabolites of 1-nitropyrene, resulting from oxidation at the K-regions, is described. Reaction of 1-nitropyrene with OsO4 gave the cis-4, 5- and 9, 10-di-hydrodiols. These were separated and oxidized with activated MnO2 to give the corresponding 4, 5- and 9, 10-diones; further oxidation to the highly mutagenic lactones, 1- and 3-nitro-5H-phenanthro[4, 5-bed]pyran-5-one, was observed in these reactions. Reduction of the 4, 5-dione with KBH4 gave the trans-4, 5-dihydrodiol, which was identical to one of the metabolites of 1-nitropyrene. Reduction of the 9, 10-dione gave an unstable trans-9, 10-dihydrodiol, which was characterized as its diacetate. The u.v. spectra, n.m.r. spectra and h.p.l.c. retention times of these compounds are presented.

AB - The synthesis of potential metabolites of 1-nitropyrene, resulting from oxidation at the K-regions, is described. Reaction of 1-nitropyrene with OsO4 gave the cis-4, 5- and 9, 10-di-hydrodiols. These were separated and oxidized with activated MnO2 to give the corresponding 4, 5- and 9, 10-diones; further oxidation to the highly mutagenic lactones, 1- and 3-nitro-5H-phenanthro[4, 5-bed]pyran-5-one, was observed in these reactions. Reduction of the 4, 5-dione with KBH4 gave the trans-4, 5-dihydrodiol, which was identical to one of the metabolites of 1-nitropyrene. Reduction of the 9, 10-dione gave an unstable trans-9, 10-dihydrodiol, which was characterized as its diacetate. The u.v. spectra, n.m.r. spectra and h.p.l.c. retention times of these compounds are presented.

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