Studies on polycyclic fluoroazaarenes: Synthesis of trans-9-fluoro-and -11-fluoro 3,4-dihydroxy-3,4-dihydrobenz[c]acridines as potential proximate carcinogenic metabolites of fluorobenz[c]-acridine

Dipanjan Pan, Gandhi K. Kar, Jayanta K. Ray, Jyh ming Lin, Shantu Amin, Suchada Chantrapromma, Hoong Kun Fun

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12 Citations (Scopus)

Abstract

Stereoselective syntheses of the title compounds trans-9-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1a and trans-11-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1b, as proximate carcinogenic metabolites of 9- and 11-fluorobenz[c]acridines, respectively, are described. In order to compare mutagenic activities with their parent fluoroazaarenes, 9-fluorobenz[c]acridine 2a and 11-fluorobenz[c]acridine 2b, have also been synthesised. The dihydrodiols were obtained by the stereoselective reduction of o-quinones, which in turn were synthesised by following the protocol of functional group transformation of methoxy→phenol→o-quinone.

Original languageEnglish (US)
Pages (from-to)2470-2475
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 1
Volume19
DOIs
StatePublished - Jan 1 2001

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Acridines
Metabolites
Quinones
Functional groups

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{025cdfedfb7448569cda2c5d499e3739,
title = "Studies on polycyclic fluoroazaarenes: Synthesis of trans-9-fluoro-and -11-fluoro 3,4-dihydroxy-3,4-dihydrobenz[c]acridines as potential proximate carcinogenic metabolites of fluorobenz[c]-acridine",
abstract = "Stereoselective syntheses of the title compounds trans-9-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1a and trans-11-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1b, as proximate carcinogenic metabolites of 9- and 11-fluorobenz[c]acridines, respectively, are described. In order to compare mutagenic activities with their parent fluoroazaarenes, 9-fluorobenz[c]acridine 2a and 11-fluorobenz[c]acridine 2b, have also been synthesised. The dihydrodiols were obtained by the stereoselective reduction of o-quinones, which in turn were synthesised by following the protocol of functional group transformation of methoxy→phenol→o-quinone.",
author = "Dipanjan Pan and Kar, {Gandhi K.} and Ray, {Jayanta K.} and Lin, {Jyh ming} and Shantu Amin and Suchada Chantrapromma and Fun, {Hoong Kun}",
year = "2001",
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language = "English (US)",
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journal = "Journal of the Chemical Society, Perkin Transactions 1",
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TY - JOUR

T1 - Studies on polycyclic fluoroazaarenes

T2 - Synthesis of trans-9-fluoro-and -11-fluoro 3,4-dihydroxy-3,4-dihydrobenz[c]acridines as potential proximate carcinogenic metabolites of fluorobenz[c]-acridine

AU - Pan, Dipanjan

AU - Kar, Gandhi K.

AU - Ray, Jayanta K.

AU - Lin, Jyh ming

AU - Amin, Shantu

AU - Chantrapromma, Suchada

AU - Fun, Hoong Kun

PY - 2001/1/1

Y1 - 2001/1/1

N2 - Stereoselective syntheses of the title compounds trans-9-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1a and trans-11-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1b, as proximate carcinogenic metabolites of 9- and 11-fluorobenz[c]acridines, respectively, are described. In order to compare mutagenic activities with their parent fluoroazaarenes, 9-fluorobenz[c]acridine 2a and 11-fluorobenz[c]acridine 2b, have also been synthesised. The dihydrodiols were obtained by the stereoselective reduction of o-quinones, which in turn were synthesised by following the protocol of functional group transformation of methoxy→phenol→o-quinone.

AB - Stereoselective syntheses of the title compounds trans-9-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1a and trans-11-fluoro-3,4-dihydroxy-3,4-dihydrobenz[c]acridine 1b, as proximate carcinogenic metabolites of 9- and 11-fluorobenz[c]acridines, respectively, are described. In order to compare mutagenic activities with their parent fluoroazaarenes, 9-fluorobenz[c]acridine 2a and 11-fluorobenz[c]acridine 2b, have also been synthesised. The dihydrodiols were obtained by the stereoselective reduction of o-quinones, which in turn were synthesised by following the protocol of functional group transformation of methoxy→phenol→o-quinone.

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