Skip to main content
Log in

Synthesis of 4-(2-hydroxymethylaryl)coumarins

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

New 4-(2-hydroxymethylaryl)coumarins were prepared using the Suzuki—Miyaura cross-coupling at the key step. According to X-ray diffraction data, the compounds obtained are structural analogs of the natural stilbene combretastatin A-4, which exhibits potent antitumor activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. D. M. X. Donnelly, G. Boland, in The Flavonoids: Advances in Research since 1986, Ed. J. B. Horborne, Chapman and Hall, London—New York, 1994, pp. 239–258.

    Google Scholar 

  2. (a)_G. R. Petit, S. B. Singh, E. Hamel, C. M. Lin, D. S. Alberts, D. Garcia-Kendall, Experientia, 1989, 45, 209; (b) G. R. Petit, S. B. Singh, M. R. Boyd, E. Hamel, R. K. Petit, J. M. Schmidt, F. J. Hogan, J. Med. Chem., 1995, 38, 1666; (c) N.-H. Nam, Curr. Med. Chem., 2003, 10, 1697; (d) G. C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, A. Genazzani, J. Med. Chem., 2006, 49, 3033; (e) A. Chaud-hary, S. N. Pandeya, P. Kumar, P. P. Sharma, S. Gupta, N. Soni, K. K. Verma, G. Bhardwaj, Mini Rev. Med. Chem., 2007, 7, 1186.

  3. T. Taechowisan, C. Lu, Y. Chen, S. Lumyong, J. Cancer Res. Ther., 2007, 3, 86.

    Article  CAS  Google Scholar 

  4. C. Bailly, C. Bal, P. Barbier, S. Combes, J.-P. Finet, M.-P. Hildebrand, V. Peyrot, N. Wattez, J. Med. Chem., 2003, 46, 5437.

    Article  CAS  Google Scholar 

  5. C. Rappl, P. Barbier, V. Bourgarel-Rey, C. Gregoire, R. Gilli, M. Carre, S. Combes, J.-P. Finet, V. Peyrot, Biochemistry, 2006, 45, 9210.

    Article  CAS  Google Scholar 

  6. (a)_M. Cushman, D. Nagaratham, D. Gopal, A. K. Chak-raborti, C. M. Lin, E. J. Hamel, J. Med. Chem., 1991, 34, 2579; (b) K. Ohsumi, T. Hatanaka, K. Fujita, R. Nakagawa, Y. Fukuda, Y. Nihei, Y. Suga, Y. Morinaga, Y. Akiyama, T. Tsuji, Bioorg. Med. Chem. Lett., 1998, 8, 3153.

  7. M. I. Naumov, S. A. Sutirin, A. S. Shavirin, O. G. Ganina, V. Bourgarel-Rey, I. P. Beletskaya, J.-P. Finet, A. Yu. Fe-dorov, J. Org. Chem., 2007, 72, 3293.

    Article  CAS  Google Scholar 

  8. (a)_M. F. Oldfield, L. Chen, N. P. Botting, Tetrahedron, 2004, 60, 1887; (b) R. A. Dixon, D. Ferreira, Phytochemis-try, 2002, 16, 205; (c) H. Adlercreutz, Lancet Oncol., 2002, 3, 364; (d) C. Morrisey, R. W. G. Watson, Curr. Drug Targets, 2003, 4, 231.

  9. (a)_N. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457; (b) A. Suzuki, J. Organomet. Chem., 1999, 576, 147; (c) P. Llord-Williams, E. Giralt, Chem. Soc. Rev., 2001, 30, 145; (d) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lamaire, Chem. Rev., 2002, 102, 1359.

  10. (a)_D. H. R. Barton, D. M. X. Donnelly, J.-P. Finet, P. G. Guiry, J. Chem. Soc., Perkin Trans. 1, 1992, 1365; (b) G. M. Boland, D. M. X. Donnelly, J.-P. Finet, M. Rea, J. Chem. Soc., Perkin Trans. 1, 1996, 2591; (c) D. M. X. Donnelly, J.-P. Finet, P. J. Guiry, M. D. Rea, Synth. Commun., 1999, 29, 2719.

  11. O. G. Ganina, E. Daras, V. Bourgarel-Rey, V. Peyrot, A. N. Andresyuk, J.-P. Finet, A. Yu. Fedorov, I. P. Beletskaya, S. Combes, Bioorg. Med. Chem., 2008, 16, 8806.

    Article  CAS  Google Scholar 

  12. (a)_T. L. Nguyen, C. McGrath, A. R. Hermone, J. C. Burnett, D. W. Zaharevitz, B. W. Day, P. Wipf, E. Hamel, R. Gussio, J. Med. Chem., 2005, 48, 6107; (b) G. C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, A. Genazzani, J. Med. Chem., 2006, 49, 3033; (c) O. N. Zefirova, A. G. Diikov, N. V. Zyk, N. S. Zefirov, Izv. Akad. Nauk, Ser. Khim., 2007, 655 [Russ. Chem. Bull., Int. Ed., 2007, 56, 680].

    Google Scholar 

  13. F. Lara-Ochoa, G. Espinosa-Pirez, Tetrahedron Lett., 2007, 48, 7007.

    Article  CAS  Google Scholar 

  14. G. M. Sheldrick, SHELXTL v.6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2000.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to A. S. Shavyrin, I. P. Beletskaya or A. Yu. Fedorov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 612–617, March, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sitnikov, N.S., Shavyrin, A.S., Fukin, G.K. et al. Synthesis of 4-(2-hydroxymethylaryl)coumarins. Russ Chem Bull 59, 626–631 (2010). https://doi.org/10.1007/s11172-010-0130-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-010-0130-3

Navigation