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

doi:10.1039/b102750f

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

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	2470-2475
Number of pages	6
Journal	Journal of the Chemical Society. Perkin Transactions 1
Volume	19
DOIs	https://doi.org/10.1039/b102750f
State	Published - 2001
Externally published	Yes

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General Chemistry

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10.1039/b102750f

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Pan, D., Kar, G. K., Ray, J. K., Lin, J. M., Amin, S., Chantrapromma, S., & Fun, H. K. (2001). 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. Journal of the Chemical Society. Perkin Transactions 1, 19, 2470-2475. https://doi.org/10.1039/b102750f

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. / Pan, Dipanjan; Kar, Gandhi K.; Ray, Jayanta K. et al.
In: Journal of the Chemical Society. Perkin Transactions 1, Vol. 19, 2001, p. 2470-2475.

Research output: Contribution to journal › Article › peer-review

Pan, D, Kar, GK, Ray, JK, Lin, JM, Amin, S, Chantrapromma, S & Fun, HK 2001, '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', Journal of the Chemical Society. Perkin Transactions 1, vol. 19, pp. 2470-2475. https://doi.org/10.1039/b102750f

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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.",

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AU - Pan, Dipanjan

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AU - Amin, Shantu

AU - Chantrapromma, Suchada

AU - Fun, Hoong Kun

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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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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

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