Tsotinis, A., Vlachou, M., R. Kelland, L. and Thurston, D.E. (2002) A New Ring-Forming Methodology for the Synthesis of Bioactive Pyrroloquinoline Derivatives. Heterocycles, 57 (1). pp. 129-133. 10.3987/COM-01-9373.
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A new, efficient, two-step method for the synthesis of bioactive pyrroloquinolines is described. Readily available nitroquinolines, bearing the nitro moiety in the carbocyclic ring, are treated with 4-chlorophenoxyacetonitrile in the presence of potassium tert-butoxide/THF to give the analogous vicarious nucleophilic substitution products (5, 8 and 11). These, in turn, are subjected to catalytic hydrogenation to produce 1H-pyrrolo[2,3-f]quinoline (6), 3H-pyrrolo[3,2-f]quinoline (9) and 1H-pyrrolo[3,2-h]quinoline (12) in good yields and relatively short reaction times. The differential activity of two N-alkylated 1H-pyrrolo[2,3-f]quinolines (1) in cisplatin resistant cell lines compared to the corresponding parent lines suggests that these might be useful leads for developing agents for use in drug resistant diseases.
|Departments, units and centres:||Department of Pharmaceutical and Biological Chemistry > Department of Pharmaceutical and Biological Chemistry|
|Journal or Publication Title:||Heterocycles|
|Deposited By:||Library Staff|
|Deposited On:||09 Mar 2012 09:16|
|Last Modified:||09 Mar 2012 09:16|
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