The synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1 and E. coli nitroreductase

Burke, Philip, Chun Wong, Lai, Jenkins, Terence, Knox, Richard and Stanforth, Stephen (2011) The synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1 and E. coli nitroreductase. Bioorganic & Medicinal Chemistry Letters, 21 (24). pp. 7447-7450. ISSN 0960-894X

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Official URL: http://dx.doi.org/10.1016/j.bmcl.2011.10.044

Abstract

A series of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines 10 and nitro-substituted 5,6-dihydrobenzimidazo[2,1-a]isoquinoline N-oxides 11 have been synthesised and evaluated as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1 (NQO1) and Escherichia coli nitroreductase (NR). Also prepared and evaluated were 2-(3,5-dinitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline 12 and 5,6-dihydro-10-nitropyrido[3″,2″:4′,5′]imidazo[2′,1′-a]isoquinoline 12-oxide 13. Both compounds 10b and 13 were reduced faster by human NQO1 than by CB-1954 [5-(aziridin-1-yl)-2,4-dinitrobenzamide].

Item Type: Article
Uncontrolled Keywords: NAD(P)H, quinone oxidoreductase 1 (NQO1), Escherichia coli nitroreductase, CB-1954, 1,2,3,4-Tetrahydroisoquinolines, Benzimidazo[2,1-a]isoquinoline N-oxides
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: Ellen Cole
Date Deposited: 19 Dec 2011 16:19
Last Modified: 10 Aug 2015 11:39
URI: http://nrl.northumbria.ac.uk/id/eprint/4308

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