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Synthesis and photophysics of acridine derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Highly fluorescent acridine derivatives were prepared by a multistep synthesis starting from 2-chlorobenzoic acid and the approapriate (aminophenyl)alkanoic acid by means of a modified Ullmann-Jourdan reaction followed by a cyclodehydration step, and by amination in the case of aminoacridine analogues. The obtained derivatives were subjected to photophysical studies (absorption and fluorescence). The compounds displayed interesting absorption behavior and high quantum yield of fluorescence. Acridine analogues bearing a free carboxylic group can serve as effective fluorescent probes in conformation analysis of peptides.

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References

  1. B. Taraporewala and J. M. Kaufmann,J. Pharm Sci.,79, 173 (1990).

    Google Scholar 

  2. G. J. Atwell, B. F. Cain, B. C. Baguley, G. J. Finlay, and W. A. Denny,J. Med. Chem.,27, 1481 (1984).

    Google Scholar 

  3. D. W. Rewcastle, G. J. Atwell, D. Chambers, B. C. Baguley, and W. A. Denny,J. Med. Chem.,29, 472 (1986).

    Google Scholar 

  4. G. J. Atwell, G. W. Rewcastle, B. C. Baguley, and W. A. Denny,J. Med. Chem.,30, 653 (1987).

    Google Scholar 

  5. W. A. Denny, G. J. Atwell, R. F. Anderson, and W. R. Wilson,J. Med. Chem.,33, 1288 (1990).

    Google Scholar 

  6. Y. Kubota and Y. Motoda,J. Phys. Chem.,84, 2855 (1980).

    Google Scholar 

  7. C-H. Tung, T. Zhu, H. Lackland, and S. Stein,Peptide Res. 5, 115 (1992).

    Google Scholar 

  8. C. Z. Dong, H. De Rocquigny, E. Remy, S. Mellac, M. C. Fournie-Zaluski, and P. B. Roques,J. Peptide Res. 50, 269 (1997).

    Google Scholar 

  9. N. Bahr, E. Tierney, and J.-L. Reymond,Tetrahedron Lett.,38, 1489 (1997).

    Google Scholar 

  10. L. Jankiewicz, J. Malicka, and W. Wiczk,Acta Biochim. Pol.,44, 277 (1997).

    Google Scholar 

  11. D. Dwojakowska, A. Debrowska, L. Jankiewicz, W. Wiczk, and K. Stachowiak,Peptides 1998, Proceedings of the 25 th European Peptide Symposium., Ed. S. Bajusz and F. Hudecz, Akademiai Kiado, Budapest, 1998, p. 632.

    Google Scholar 

  12. J. R. Pfister, I. T. Harrison, and J. H. Fried, U.S. Patent 3 835 139, 1974;Chem. Abstr. 82, 16711 (1979).

    Google Scholar 

  13. L. G. Arnaut and S. J. Formosinho,J. Photochem. Photobiol. A: Chem.,75, 1 (1993).

    Google Scholar 

  14. G. W. Rewcastle and A. Denny,Synthesis, 217 (1985).

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Authors
  1. A. Szymanska
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  2. W. Wiczk
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  3. L. Lankiewicz
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Additional information

Faculty of Chemistry, University of Gdansk, Sobieskiego 18 80-952, Gdansk, Poland; e-mail: neta@chemik.chem.univ.gda.pl Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 914–921, July, 2000.

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Szymanska, A., Wiczk, W. & Lankiewicz, L. Synthesis and photophysics of acridine derivatives. Chem Heterocycl Compd 36, 801–808 (2000). https://doi.org/10.1007/BF02256913

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  • DOI: https://doi.org/10.1007/BF02256913

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