An expeditious four-step synthesis of the 1H-pyrrolo[2,3-f]quinoline-2-carboxamides (5a-h ) is described. Readily available 6-quinolinecarboxaldehyde is converted to the parent acid (6) by nucleophilic attack of the azido-ester (9) and intramolecular cyclization of (10 ) followed by hydrolysis of the methyl ester (11 ). The cytotoxicity of the target molecules (5a-h ) was evaluated in four tumour cell lines in vitro. One compound (5d) showed sufficient activity (IC 50 = 10.2 µM) in the human non-small cell lung cell line NSCLC-N16-L16 to be worthy of further study.

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A facile synthesis of the C4-substituted isoquinolines 5a-c and 6a-c is described. Commercially available 4-bromoisoquinoline is converted to the α,β-unsaturated esters 8 and 10 on treatment with the appropriate acrylate ester under Heck reaction conditions. The saturated amides 5a-c were obtained from the reaction of ester 9 with the requisite primary amine. Similarly the unsaturated analogues 6a-c were prepared by reacting ester 10 with the appropriate amine. The cytotoxicity of the target molecules was evaluated in two tumour cell lines in vitro. Two compounds, 6b and 6c, showed sufficient activity in the human non-small cell lung cancer line NSCLC-N16-L16 to be worthy of further study.