A New Ring-Forming Methodology for the Synthesis of Bioactive Pyrroloquinoline Derivatives

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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DOI: 10.3987/COM-01-9373

Abstract

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.

Item Type:Article
Departments, units and centres:Department of Pharmaceutical and Biological Chemistry > Department of Pharmaceutical and Biological Chemistry
ID Code:2922
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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