DOI QR코드

DOI QR Code

2,4-Diaryl Benzofuro[3,2-b]pyridine Derivatives: Design, Synthesis, and Evaluation of Topoisomerase Inhibitory Activity and Cytotoxicity

  • Received : 2013.07.16
  • Accepted : 2013.07.29
  • Published : 2013.10.20

Abstract

Designed and synthesized twenty-four 2,4-diaryl benzofuro[3,2-b]pyridine derivatives were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Various aryl groups such as phenyl, 2- or 3- furyl, 2- or 3-thienyl, and 2-pyridyl were substituted at 2- or 4- position of central pyridine. Compounds 8, 12, 13, and 14, with 2-furyl either at 2- or 4- position of central pyridine showed the significant topoisomerase II inhibitory activity at 100 ${\mu}M$.

Keywords

References

  1. Wang, J. C. Annu. Rev. Biochem. 1996, 65, 635. https://doi.org/10.1146/annurev.bi.65.070196.003223
  2. Nitiss, J. L. Biochim. Biophys. Acta 1998, 1400, 63. https://doi.org/10.1016/S0167-4781(98)00128-6
  3. Cummings, J.; Smyth, J. F. Ann. Oncol. 1993, 4, 533.
  4. Chen, A. Y.; Liu, L. F. Ann. Rev. Pharmacol. Toxicol. 1994, 34, 191. https://doi.org/10.1146/annurev.pa.34.040194.001203
  5. Holden, J. A. Curr. Med. Chem. Anticancer Agent 2001, 1, 1. https://doi.org/10.2174/1568011013354859
  6. Zhao, L. X.; Kim, T. S.; Ahn, S. H.; Kim, T. H.; Kim, E. K.; Cho, W. J.; Choi, H. S.; Lee, C. S.; Kim, J. A.; Jeong, T. C.; Chang, C.-J.; Lee, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 2659. https://doi.org/10.1016/S0960-894X(01)00531-5
  7. Zhao, L. X.; Moon, Y. S.; Basnet, A.; Kim, E. K.; Jahng, Y.; Park, J. G.; Jeong, T. C.; Cho, W. J.; Choi, S. U.; Lee, C. O.; Lee, S. Y.; Lee, C. S.; Lee, E. S. Bioorg. Med. Chem. Lett. 2004, 14, 1333. https://doi.org/10.1016/j.bmcl.2003.11.084
  8. Zhao, L. X.; Sherchan, J.; Park, J. K.; Jahng, Y.; Jeong, B. S.; Jeong, T. C.; Lee, C. S.; Lee, E. S. Arch. Pharm. Res. 2006, 29, 1091. https://doi.org/10.1007/BF02969297
  9. Basnet, A.; Thapa, P.; Karki, R.; Na, Y.; Jahng, Y.; Jeong, B. S.; Jeong, T. C.; Lee, C. S.; Lee, E. S. Bioorg. Med. Chem. 2007, 15, 4351. https://doi.org/10.1016/j.bmc.2007.04.047
  10. Son, J. K.; Zhao, L. X.; Basnet, A.; Thapa, P.; Karki, R.; Na, Y.; Jahng, Y.; Jeong, T. C.; Jeong, B. S.; Lee, C. S.; Lee, E.S. Eur. J. Med. Chem. 2008, 43, 675. https://doi.org/10.1016/j.ejmech.2007.05.002
  11. Thapa, P.; Karki, R.; Basnet, A.; Thapa, U.; Choi, H. Y.; Na, Y.; Jahng, Y.; Lee, C. S.; Kwon, Y.; Jeong, B. S.; Lee, E.S. Bull. Korean Chem. Soc. 2008, 29, 1605. https://doi.org/10.5012/bkcs.2008.29.8.1605
  12. Basnet, A.; Thapa, P.; Karki, R.; Choi, H. Y.; Choi, J. H.; Yun, M.; Jeong, B. S.; Jahng, Y.; Na, Y.; Cho, W. J.; Kwon, Y.; Lee, C. S.; Lee, E. S. Bioorg. Med. Chem. Lett. 2010, 20, 42. https://doi.org/10.1016/j.bmcl.2009.11.041
  13. Thapa, P.; Karki, R.; Thapa, U.; Jahng, Y.; Jung, M. J.; Nam, J. M.; Na, Y.; Kwon, Y.; Lee, E.S. Bioorg. Med. Chem. 2010, 18, 377. https://doi.org/10.1016/j.bmc.2009.10.049
  14. Thapa, P.; Karki, R.; Choi, H. Y.; Choi, J. H.; Yun, M.; Jeong, B. S.; Jung, M. J.; Nam, J. M.; Na, Y.; Cho, W. J.; Kwon, Y.; Lee, E. S. Bioorg. Med. Chem. 2010, 18, 2245. https://doi.org/10.1016/j.bmc.2010.01.065
  15. Karki, R.; Thapa, P.; Kang, M. J.; Jeong, T. C.; Nam, J. M.; Kim, H. L.; Na, Y.; Cho, W. J.; Kwon, Y.; Lee, E. S. Bioorg. Med. Chem. 2010, 18, 3066. https://doi.org/10.1016/j.bmc.2010.03.051
  16. Karki, R.; Thapa, P.; Yoo, H. Y.; Kadayat, T. M.; Park, P. H.; Na, Y.; Lee, E.; Jeon, K. H.; Cho, W. J.; Choi, H.; Kwon, Y.; Lee, E. S. Eur. J. Med. Chem. 2012, 49, 219. https://doi.org/10.1016/j.ejmech.2012.01.015
  17. Thapa, P.; Karki, R.; Yun, M.; Kadayat, T. M.; Lee, E.; Kwon, H. B.; Na, Y.; Cho, W. J.; Kim, N. D.; Jeong, B.-S.; Kwon, Y.; Lee, E. S. Eur. J. Med. Chem. 2012, 52, 123. https://doi.org/10.1016/j.ejmech.2012.03.010
  18. Jeong, B. S.; Choi, H. Y.; Thapa, P.; Karki, R.; Lee, E.; Nam, J. M.; Na, Y.; Ha, E. M.; Kwon, Y.; Lee, E. S. Bull. Korean Chem. Soc. 2011, 32, 303. https://doi.org/10.5012/bkcs.2011.32.1.303
  19. Thapa, P.; Karki, R.; Yun, M.; Choi, J. H.; Jahng, Y.; Lee, E.; Jeon, K. H.; Na, Y.; Ha, E. M.; Cho, W. J.; Kwon, Y.; Lee, E.-S. Eur. J. Med. Chem. 2011, 46, 3201. https://doi.org/10.1016/j.ejmech.2011.04.029
  20. Thapa, P.; Karki, R.; Yoo, H. Y.; Park, P. H.; Lee, E.; Jeon, K. H.; Na, Y.; Cho, W. J.; Kwon, Y.; Lee, E.-S. Bioorg. Chem. 2012, 40, 67. https://doi.org/10.1016/j.bioorg.2011.09.001
  21. Gorlitzer, K.; Kramer, C. Pharmazie 2000, 55, 587.
  22. Mederski, W. W. K. R.; Osswald, M.; Dorsch, D.; Christadler, M.; Schmitges, C. J.; Wilm, C. Bioorg. Med. Chem. Lett. 1999, 9, 619. https://doi.org/10.1016/S0960-894X(99)00040-2
  23. Khan, I. A.; Kulkarni, M. V.; Gopal, M.; Shahabuddin, M. S.; Sun, C. M. Bioorg. Med. Chem. Lett. 2005, 15, 3584. https://doi.org/10.1016/j.bmcl.2005.05.063
  24. Yamato, M.; Takeuchi, Y.; Hashigaki, K.; Ikeda, Y.; Mingrong, C.; Takeuchi, K.; Matsushima, M.; Tsuruo, T.; Tashiro, T.; Tsukagoshi, S.; Yamashita, Y.; Nakano, H. J. Med. Chem. 1989, 32, 1295. https://doi.org/10.1021/jm00126a025
  25. Deady, L. W.; Kaye, A. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1997, 40, 2040. https://doi.org/10.1021/jm970044r
  26. Deady, L. W.; Denny, W. A.; Kaye, A. J. PCT Int. Appl. WO 9845272 A1 19981015, 1998.
  27. Staker, B. L.; Hjerrild, K.; Feese, M. D.; Behnke, C. A.; Burgin Jr., A. B.; Stewart, L. Proc. Natl. Acad. Sci. USA 2002, 99, 15387. https://doi.org/10.1073/pnas.242259599
  28. Hurley, L. H. Nat. Rev. Cancer 2002, 2, 188. https://doi.org/10.1038/nrc749
  29. Lee, S. H.; Van, H. T. M.; Yang, S. H.; Lee, K. T.; Kwon, Y.; Cho, W. J. Bioorg. Med. Chem. Lett. 2009, 19, 2444. https://doi.org/10.1016/j.bmcl.2009.03.058
  30. Mak, M.; Nogradi, M.; Szollosy, A. Tetrahedron 2006, 62, 8425. https://doi.org/10.1016/j.tet.2006.06.016
  31. Morimoto, M.; Fukumoto, H.; Nozoe, T.; Hagiwara, A.; Komai, K. J. Agric. Food Chem. 2007, 55, 700. https://doi.org/10.1021/jf062562t
  32. Loser, R.; Chlupacova, M.; Marecek, A.; Opletalova, V.; Gutschow, M. Helv. Chim. Acta 2004, 87, 2597. https://doi.org/10.1002/hlca.200490232
  33. Krohnke, F. Synthesis 1976, 1.
  34. Jun, K. Y.; Lee, E. Y.; Jung, M. J.; Lee, O. H.; Lee, E. S.; Park Choo, H. Y.; Na, Y.; Kwon, Y. Eur. J. Med. Chem. 2011, 46, 1964. https://doi.org/10.1016/j.ejmech.2011.01.011
  35. Wu, C. C.; Li, T. K.; Farh, L.; Lin, L. Y.; Lin, T. S.; Yu, Y. J.; Yen, T. J.; Chiang, C. W.; Chan, N. L. Science 2011, 333, 459. https://doi.org/10.1126/science.1204117
  36. Wendorff, T. J.; Schmidt, B. H.; Heslop, P.; Austin, C. A.; Berger, J. M. J. Mol. Biol. 2012, 424, 109. https://doi.org/10.1016/j.jmb.2012.07.014
  37. Marti-Renom, M. A.; Stuart, A. C.; Fiser, A.; Sanchez, R.; Melo, F.; Sali, A. Annu. Rev. Biophys. Biomol. Struct. 2000, 29, 291.
  38. Dolinsky, T. J.; Czodrowski, P.; Li, H.; Nielsen, J. E.; Jensen, J. H.; Klebe, G.; Baker, N. A. Nucleic Acids Res. 2007, 35, W522. https://doi.org/10.1093/nar/gkm276
  39. Case, D. A.; Cheatham, T. E. 3rd.; Darden, T.; Gohlke, H.; Luo, R.; Merz, K. M., Jr.; Onufriev, A.; Simmerling, C.; Wang, B.; Woods, R. J. J. Comput. Chem. 2005, 26, 1668. https://doi.org/10.1002/jcc.20290
  40. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comput. Chem. 2009, 30, 2785. https://doi.org/10.1002/jcc.21256
  41. Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455.

Cited by

  1. -Catalyzed [4 + 1] Annulations of 2-Hydroxy- and 2-Aminobenzaldehydes with Allenes: A Simple Method toward 3-Coumaranones and 3-Indolinones vol.17, pp.15, 2015, https://doi.org/10.1021/acs.orglett.5b01825
  2. A Series of Novel Terpyridine-Skeleton Molecule Derivants Inhibit Tumor Growth and Metastasis by Targeting Topoisomerases vol.58, pp.3, 2015, https://doi.org/10.1021/jm501023q
  3. -2,3-Dihydrobenzofuran-3-ols by Aqueous Transfer Hydrogenation via Dynamic Kinetic Resolution vol.36, pp.7, 2017, https://doi.org/10.1021/acs.organomet.7b00022
  4. Bifunctional N-Heterocyclic Carbene Catalyzed [3+4] Annulation of Enals and Aurones vol.21, pp.5, 2014, https://doi.org/10.1002/chem.201405828
  5. 2-Chlorophenyl-substituted benzofuro[3,2-b]pyridines with enhanced topoisomerase inhibitory activity: The role of the chlorine substituent vol.27, pp.15, 2013, https://doi.org/10.1016/j.bmcl.2017.06.025
  6. Temperature-Controlled Desulfonylative Condensation of α-Sulfonyl o-Hydroxyacetophenones and 2-Formyl Azaarenes: Synthesis of Azaaryl Aurones and Flavones vol.84, pp.1, 2013, https://doi.org/10.1021/acs.joc.8b02857
  7. Aurones: Synthesis and Properties vol.55, pp.4, 2013, https://doi.org/10.1007/s10593-019-02457-x
  8. Copper-Catalyzed Alkynylation/Cyclization/Isomerization Cascade for Synthesis of 1,2-Dihydrobenzofuro[3,2-b]pyridines and Benzofuro[3,2-b]pyridines vol.84, pp.23, 2013, https://doi.org/10.1021/acs.joc.9b02512
  9. Discovery of a 2,4-diphenyl-5,6-dihydrobenzo(h)quinolin-8-amine derivative as a novel DNA intercalating topoisomerase IIα poison vol.226, pp.None, 2013, https://doi.org/10.1016/j.ejmech.2021.113860