Synthesis of linear and angular furocoumarins and difurocoumarins has been carried out starting from substituted coumarins and phenyl acetylene leading to the target compounds via styrylcoumarin intermediates. The average yields are higher than those reported before. Newly synthesized furocoumarin and difurocoumarin derivatives were evaluated for inhibition of cell proliferation of human breast carcinoma, human gastric carcinoma, and human lung cancer, exhibiting antiproliferative activity. New difurocoumarin derivative 4-methyl-6,9-diphenyl-2H-difuro[3,2-f:2',3'-h]chromen-2-one exhibited the highest inhibition of cell proliferation on all cell lines.
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(a) Chang, M.-S.; Yang, Y.-C.; Kuo, Y.-C.; Kuo, Y.-H.; Chang, C.; Chen, C.-M.; Lee, T.-H. J. Nat. Prod. 2005, 68, 11. (b) Ito, C.; Itoigawa, M.; Katsuno, S.; Omura, M.; Tokuda, H.; Nishino, H.; Furukawa, H. J. Nat. Prod. 2000, 63, 1218.
(a) Keating, G. J.; O'Kennedy, R. The Chemistry and Occurrence of Coumarins. Coumarins: Biology, Applications and Mode of Action; O'Kennedy, R.; Thornes, R. D., Eds.; John Wiley&Sons: Chichester, New-York, 1997, p. 23. (b) Shikishima, Y.; Takaishi, Y.; Honda, H.; Ito, M.; Takeda, Y.; Kodzhimatov, O. K.; Ashurmetov, O.; Lee, K.-H. Chem. Pharm. Bull. 2001, 49, 877.
Sancho, R.;. Marquez, N; Gomez-Gonzalo, G.; Calzado, M.; Bettoni, G.; Coiras, M. T.; Alcami, J.; Lopez-Cabrera, M.; Appendino, G.; Munoz, E. J. Biol. Chem. 2004, 279, 37349.
Serrano-Pérez, J. J.; Merchán, M.; Serrano-Andrés, L. J. Phys. Chem. B. 2008, 112, 14002.
Tsai, C.-J.; Chen, C.-C.; Tsai, C.-W.; Wu, M-J. J. Org. Chem. 2016, 81, 3882.
Borges, F.; Pinto, M. Helv. Chim. Acta. 1992, 75, 1061.
Soman, S. S.; Trivedi, K. N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1992, 31B, 532.
Kazuaki, O.; Naozumi, N.; Yukio, T.; Yuki, Y.; Teruki, Y.; Keiji, W.; Minoru, M. Heterocycles 2005, 65, 1985.
Weber, U. S.; Steffen, B.; Siegers, C. P. Res. Commun. Mol. Pathol. Pharmacol. 1998, 99, 193.
Wu, L.; Wang, X.; Xu, W.; Farzaneh, F.; Xu, R. Curr. Med. Chem. 2009, 16, 4236.
Lau, C. S.; Ho, C. Y.; Kim, C. F.; Leung, K. N; Fung, K. P; Tse, T. F.; Chan, H. L.; Chow, M. S. Life Sci. 2004, 75, 797.
Zeba, N. S.; Mohammad, A. Indian J. Chem. 2006, 45B, 2704.
Masahiko, Y.; Mieko, A.; Kenji, O.; Kuninobu, K.; Masahiro, H.; Tadafumi, U. J. Org. Chem. 1998, 63, 7298.
Hsieh, H.-P.; Chang, J.-Y.; Kuo, C.-C.; Chao, Y.-S. US Patent 20090312317.
Finn, G. J.; Kenealy, E.; Creaven, B. S.; Egan, D. A. Cancer Lett. 2002, 183, 61.
Wietrzyk, J.; Chodynski, M.; Fitak, H.; Wojdat, E.; Kutner, A.; Opolski, A. Anticancer Drugs 2007, 18, 447.
We thank Dr. Litinas, Professor of Organic Chemistry and staff of Faculty of Sciences, Aristotle University of Thessaloniki, Greece, for providing the facilities for instrumental analysis and Bioassay-Cell Culture Laboratory, National Research Centre, El-Tahrir St., Dokki, Cairo 12622, Egypt, for conducting the biological tests.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 867–870
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Selim, Y., El-Ahwany, M. Synthesis and antiproliferative activity of new furocoumarin derivatives. Chem Heterocycl Comp 53, 867–870 (2017). https://doi.org/10.1007/s10593-017-2139-0
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DOI: https://doi.org/10.1007/s10593-017-2139-0