A facile synthesis of C2-substituted pyrrolo[2,3-f]quinolines with cytotoxic activity

Andrew Tsotinis, Margarita Vlachou, Spyridon Zouroudis, A. Jeney, Ferenc Timár, David E. Thurston, Christos Roussakis

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

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 (IC50 = 10.2 μM) in the human non-small cell lung cell line NSCLC-N16-L16 to be worthy of further study.

Original languageEnglish
Pages (from-to)189-192
Number of pages4
JournalLetters in Drug Design and Discovery
Volume2
Issue number3
DOIs
Publication statusPublished - May 2005

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Esters
Cyclization
Tumor Cell Line
Inhibitory Concentration 50
Hydrolysis
Cell Line
Lung
Acids
pyrrolo(2,3-f)quinoline
In Vitro Techniques

Keywords

  • Cytotoxicity
  • Pyrrolo[2,3-f]quinolines
  • Synthesis

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Molecular Medicine

Cite this

A facile synthesis of C2-substituted pyrrolo[2,3-f]quinolines with cytotoxic activity. / Tsotinis, Andrew; Vlachou, Margarita; Zouroudis, Spyridon; Jeney, A.; Timár, Ferenc; Thurston, David E.; Roussakis, Christos.

In: Letters in Drug Design and Discovery, Vol. 2, No. 3, 05.2005, p. 189-192.

Research output: Contribution to journalArticle

Tsotinis, A, Vlachou, M, Zouroudis, S, Jeney, A, Timár, F, Thurston, DE & Roussakis, C 2005, 'A facile synthesis of C2-substituted pyrrolo[2,3-f]quinolines with cytotoxic activity', Letters in Drug Design and Discovery, vol. 2, no. 3, pp. 189-192. https://doi.org/10.2174/1570180053765075
Tsotinis, Andrew ; Vlachou, Margarita ; Zouroudis, Spyridon ; Jeney, A. ; Timár, Ferenc ; Thurston, David E. ; Roussakis, Christos. / A facile synthesis of C2-substituted pyrrolo[2,3-f]quinolines with cytotoxic activity. In: Letters in Drug Design and Discovery. 2005 ; Vol. 2, No. 3. pp. 189-192.
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