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Vol. 31 No. 4 (2019): Vol 31 Issue 4

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Microwave Assisted One-Pot Three-Component Synthesis of Novel Pyranocarbazole Derivatives as Antiproliferative Agents and Molecular Docking Studies

https://doi.org/10.14233/ajchem.2019.21725
Bobbala Ramana Reddy
Department of Chemistry, School of Technology, GITAM University, Hyderabad-502102, India
Pedavenkatagari Narayana Reddy
Department of Chemistry, School of Technology, GITAM University, Hyderabad-502102, India

Corresponding Author(s) : Bobbala Ramana Reddy

bobbala.ramana91@gmail.com

Asian Journal of Chemistry, Vol. 31 No. 4 (2019): Vol 31 Issue 4

Abstract

A new series of pyrano[3,2-c]carbazole and pyrano[2,3-a]carbazole derivatives have been synthesized by one-pot three-component coupling of 4-hydroxycarbazole or 2-hydroxycarbazole, aromatic substituted aldehydes and (E)-N-methyl-1-(methylthio)-2-nitroethenamine under microwave irradiation. This transformation presumably occurs via Knoevenagel condensation-Michael addition–tautomerism intramolecular O-cyclization-elimination sequence of reactions creating one C-O bond and two C-C bonds. The significant features of this one-pot reaction include catalyst free, solvent free, atom-economy, no column chromatographic purification, short reaction time and good yield. Further, the synthesized pyranocarbazole derivatives were evaluated for their antiproliferative activity against four cancer cell lines such as DU 145 (prostate cancer), MDA-MB-231 (breast cancer), SKOV3 (ovarian cancer) and B16-F10 (skin cancer). The results clearly demonstrated that trimethoxyphenyl substituted pyrano[3,2-c]carbazole (9h) exhibited most potent antriproliferative activity against tested cell lines. Compounds 9a, 9b and 11a were also displayed pronounced antriproliferative activity. In addition, molecular docking studies revealed that the lead compounds bind to the colchicine binding site of the tubulin effectively.

Keywords

Microwave Pyranocarbazole Antiproliferative Molecular docking
Reddy, B. R., & Reddy, P. N. (2019). Microwave Assisted One-Pot Three-Component Synthesis of Novel Pyranocarbazole Derivatives as Antiproliferative Agents and Molecular Docking Studies. Asian Journal of Chemistry, 31(4), 785–792. https://doi.org/10.14233/ajchem.2019.21725
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References
  1. A.W. Schmidt, K.R. Reddy and H.J. Knolker, Chem. Rev., 112, 3193 (2012); https://doi.org/10.1021/cr200447s.
  2. H.J. Knolker and K.R. Reddy, Chem. Rev., 102, 4303 (2002); https://doi.org/10.1021/cr020059j.
  3. H.J. Knolker, Curr. Chem., 244, 115 (2005); https://doi.org/10.1007/b96890.
  4. H.J. Knolker, K.R. Reddy and G.A. Cordell, The Alkaloids, Academic Press: London, pp. 1-430 (2008).
  5. F.A. Tanious, W.D. Wilson, D.A. Patrick, R.R. Tidwell, P. Colson, C. Houssier, C. Tardy and C. Bailly, Eur. J. Biochem., 268, 3455 (2001); https://doi.org/10.1046/j.1432-1327.2001.02242.x.
  6. C.C. Chang, I.C. Kuo, J.J. Lin, Y.C. Lu, C.T. Chen, H.T. Back, P.J. Lou and T.C. Chang, Chem. Biodivers., 1, 1377 (2004); https://doi.org/10.1002/cbdv.200490100.
  7. M.J. Hsu, Y. Chao, Y.H. Chang, F.M. Ho, Y.L. Huang, L.J. Huang, T.Y. Luh, C.P. Chen and W.W. Lin, Biochem. Pharmacol., 70, 102 (2005); https://doi.org/10.1016/j.bcp.2005.04.014.
  8. A.R. Howard-Jones and C.T. Walsh, J. Am. Chem. Soc., 128, 12289 (2006); https://doi.org/10.1021/ja063898m.
  9. L. Hu, Z. Li, Y. Li, J. Qu, Y.H. Ling, J. Jiang and D.W. Boykin, J. Med. Chem., 49, 6273 (2006); https://doi.org/10.1021/jm060546h.
  10. R.S. Ramsewak, M.G. Nair, G.M. Strasburg, D.L. DeWitt and J.L. Nitiss, J. Agric. Food Chem., 47, 444 (1999); https://doi.org/10.1021/jf9805808.
  11. I. Mester and J. Reisch, Ann. Chem., 10, 1725 (1977); https://doi.org/10.1002/jlac.197719771019.
  12. S. Syam, A.B. Abdul, M.A. Sukari, S. Mohan, S.I. Abdelwahab and T.S. Wah, Molecules, 16, 7155 (2011); https://doi.org/10.3390/molecules16087155.
  13. C.B. Cui, S.Y. Yan, B. Cai and X.S. Yao, J. Asian Nat. Prod. Res., 4, 233 (2002); https://doi.org/10.1080/1028602021000049041.
  14. Y. Tachibana, H. Kikuzaki, L.H. Lajis and N. Nakatani, J. Agric. Food Chem., 51, 6461 (2003); https://doi.org/10.1021/jf034700+.
  15. M. Itoigawa, Y. Kashiwada, C. Ito, H. Furukawa, Y. Tachibana, K.F. Bastow and K.-H. Lee, J. Nat. Prod., 63, 893 (2000); https://doi.org/10.1021/np000020e.
  16. C. Ito, M. Itoigawa, A. Sato, C.M. Hasan, M.A. Rashid, H. Tokuda, T. Mukainaka, H. Nishino and H. Furukawa, J. Nat. Prod., 67, 1488 (2004); https://doi.org/10.1021/np0400611.
  17. C. Ito, S. Katsuno, M. Itoigawa, N. Ruangrungsi, T. Mukainaka, M. Okuda, Y. Kitagawa, H. Tokuda, H. Nishino and H. Furukawa, J. Nat. Prod., 63, 125 (2000); https://doi.org/10.1021/np990285x.
  18. C. Ito, S. Katsuno, N. Ruangrungsi and H. Furukawa, Chem. Pharm. Bull. (Tokyo), 46, 344 (1998); https://doi.org/10.1248/cpb.46.344.
  19. K. Prasad and O. Revu, Synthesis, 44, 2243 (2012); https://doi.org/10.1055/s-0031-1291154.
  20. K. Prabakaran, M. Zeller and K.J.R. Prasad, Synlett, 13, 1835 (2011); https://doi.org/10.1055/s-0030-1260965.
  21. K.K. Gruner, T. Hopfmann, K. Matsumoto, A. Jager, T. Katsuki and H.J. Knolker, Org. Biomol. Chem., 9, 2057 (2011); https://doi.org/10.1039/c0ob01088j.
  22. M. Sridharan and K.J.R. Prasad, Z. Naturforsch. B, 63, 1112 (2008); https://doi.org/10.1515/znb-2008-0916.
  23. R. Hesse, K.K. Gruner, O. Kataeva, A.W. Schmidt and H.-J. Knölker, Chem. Eur. J., 19, 14098 (2013); https://doi.org/10.1002/chem.201301792.
  24. V.P. Kumar, K.K. Gruner, O. Kataeva and H.J. Knolker, Angew. Chem. Int. Ed., 52, 11073 (2013); https://doi.org/10.1002/anie.201305993.
  25. R. Hesse, A. Jager, A.W. Schmidt and H.J. Knolker, Org. Biomol. Chem., 12, 3866 (2014); https://doi.org/10.1039/C4OB00367E.
  26. K.K. Julich-Gruner, O. Kataeva, A.W. Schmidt and H.J. Knolker, Chem. Eur. J., 20, 8536 (2014); https://doi.org/10.1002/chem.201403143.
  27. R. Hesse, O. Kataeva, A.W. Schmidt and H.J. Knolker, Chem. Eur. J., 20, 9504 (2014); https://doi.org/10.1002/chem.201403645.
  28. C. Gassner, R. Hesse, A.W. Schmidt and H.J. Knolker, Org. Biomol. Chem., 12, 6490 (2014); https://doi.org/10.1039/C4OB01151A.
  29. R. Hesse, A.W. Schmidt and H.J. Knolker, Tetrahedron, 71, 3485 (2015); https://doi.org/10.1016/j.tet.2015.03.064.
  30. C. Schuster, K.K. Julich-Gruner, H. Schnitzler, R. Hesse, A. Jager, A.W. Schmidt and H.J. Knolker, J. Org. Chem., 80, 5666 (2015); https://doi.org/10.1021/acs.joc.5b00630.
  31. C. Schuster, M. Ronnefahrt, K.K. Julich-Gruner, A. Jager, A.W. Schmidt and H.J. Knolker, Synthesis, 48, 150 (2016); https://doi.org/10.1055/s-0035-1560359.
  32. T. Wang and T.R. Hoye, J. Am. Chem. Soc., 138, 13870 (2016); https://doi.org/10.1021/jacs.6b09628.
  33. W. Zhang, J. Wang, J. Mao, L. Hu, X. Wu and C. Guo, Tetrahedron Lett., 57, 1985 (2016); https://doi.org/10.1016/j.tetlet.2016.03.081.
  34. K.R. Reddy, A.S. Reddy, D.K. Dhaked, S.K. Rasheed, A.S. Pathania, R. Shankar, F. Malik and P. Das, Org. Biomol. Chem., 13, 9285 (2015); https://doi.org/10.1039/C5OB01295C.
  35. Y. Liu, Y. Guo, F. Ji, D. Gao, C. Song and J. Chang, J. Org. Chem., 81, 4310 (2016); https://doi.org/10.1021/acs.joc.6b00729.
  36. S. Kotha, R. Ali and M. Saifuddin, Tetrahedron, 71, 9003 (2015); https://doi.org/10.1016/j.tet.2015.09.044.
  37. S. Hou, Y. Liu, Y. Kong and M.L. Brown, Org. Lett., 17, 2298 (2015); https://doi.org/10.1021/acs.orglett.5b00422.
  38. P. Padmaja, G. Koteswara Rao, A. Indrasena, B.V. Subba Reddy, N. Patel, A.B. Shaik, N. Reddy, P.K. Dubey and M.P. Bhadra, Org. Biomol. Chem., 13, 1404 (2015); https://doi.org/10.1039/C4OB02015D.
  39. P. Padmaja, B.V.S. Reddy, N. Jain, S.R. Mutheneni, P. Bollepelli, S. Polepalli, G. Rambabu and P.N. Reddy, New J. Chem., 40, 8305 (2016); https://doi.org/10.1039/C6NJ01580H.
  40. P.N. Reddy, P. Padmaja, B.R. Reddy, G. Rambabu and M.P. Kumar, Med. Chem. Res., 25, 2093 (2016); https://doi.org/10.1007/s00044-016-1676-x.
  41. P.N. Reddy, P. Padmaja, B.R. Reddy and S.S. Jadav, Med. Chem. Res., 26, 2243 (2017); https://doi.org/10.1007/s00044-017-1927-5.
  42. P. Padmaja and N. Reddy, Curr. Org. Synth., 12, 3 (2015); https://doi.org/10.2174/1570179411666140806005540.
  43. P.N. Reddy and P. Padmaja, ARKIVOC, 244 (2015); https://doi.org/10.3998/ark.5550190.p008.822.
  44. P. Padmaja and P.N. Reddy, Lett. Org. Chem., 14, 115 (2017); https://doi.org/10.2174/1570178614666170123123526.
  45. P. Prasad, A. Shuhendler, P. Cai, A.M. Rauth and X.Y. Wu, Cancer Lett., 334, 263 (2013); https://doi.org/10.1016/j.canlet.2012.08.008.
  46. Y. Lu, J. Chen, M. Xiao, W. Li and D.D. Miller, Pharm. Res., 29, 2943 (2012); https://doi.org/10.1007/s11095-012-0828-z.
  47. A. Dorléans, B. Gigant, R.B.G. Ravelli, P. Mailliet, V. Mikol and M. Knossow, Proc. Natl. Acad. Sci. (USA), 106, 13775 (2009); https://doi.org/10.1073/pnas.0904223106.
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