Vol. 12 No. 2 (2013): Mapana - Journal of Sciences
Research Articles

Synthesis of a New Series of Quinolinoxymethylcoumarins as Potent Anticancer Agents

  • D Shamala,
  • K Shivashankar,
  • Rasal P Vijaykumar,
  • Pandi Vineela
D Shamala
PG Department of Chemistry, Central College Campus, Bangalore University, (DCCCBU) Bangalore- 560001, Karnataka, India;
Bio
K Shivashankar
DCCCBU
Bio
Rasal P Vijaykumar
Department of Pharmacology, KLES’s College of Pharmacy
Bio
Pandi Vineela
DPKLECP
Bio
DOI: https://doi.org/10.12723/mjs.25.5

Published 2021-08-27

Keywords

  • 4-Bromomethylcoumarins,
  • Coumarins,
  • Quinoline,
  • Cytotoxic activity.

Copyright (c) 2013

Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Abstract

4-Bromomethylcoumarins (1a-f) were reacted with 8-hydroxyquinoline to yield quinolinoxymethylcoumarins (2a-f). The structure of all the synthesized compounds were confirmed by spectral studies and screened for their anticancer activities against Dalton’s Ascitic lymphoma (DAL) and Ehrlich Ascites Carcinoma (EAC) cell lines.  Out of these, compound (2b) (R = 6-OMe) was found to be the most potent cytotoxic compound against DAL and EAC cell lines.            

References

  1. B. N. Acharya, D. Thavaselvam and M. P. Kaushik, “Synthesis and antimalarial evalution of novel pyridine quinoline hydrids”, Med. Chem. Res., 17, 487- 494, 2008. doi: 10.1007/s00044-008-9092-5
  2. P. Barraja, D. Patrizia, M. Alessandra, D. Gaetano, C. Girola, G. Viola, V. Daniel and D. Francesco, “Pyrrolo[2,3-h]quinolinones: A new ring system with potent photoantiproliferative activity”, Bioorg. Med. Chem., 14, 8712–8728, 2006. doi:10.1016/j.bmc.2006.07.061
  3. M. Robert, J. Jampilek, K. Katarina, D. R. Richardson, D. Kalinowski, P. Barbara, F. Jacek, N. Halina, A. Palkaa and J. Polanskia, “Investigating biological activity spectrum for novel quinoline analogues”, Bioorg. Med. Chem., 15, 1280-1288, 2007. doi:10.1016/j.bmc.2006.11.020
  4. R. L. Harshani, K. Aslamuzzaman, L. Yunting, Robert, G. Yiyu, S. Jain, K. Daniel, S. Daniel, C. G. Wayne, M. S. Said, “Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors”, Bioorg. Med. Chem., 18, 5576-5592, 2010. doi: 10.1016/j.bmc.2010.06.038
  5. K. V. Shashidhara, K. Abdesh, G. Bhatia, M. M. Khan, A. K. Khanna and J. K. Saxena, “Antidyslipidemic and antioxidative activities of 8-hydroxyquinoline derived novel keto-enamine schiffs bases”, Eur. J. Med. Chem., 44, 1813-1818, 2009. doi:10.1016/j.ejmech.2008.08.004
  6. M. M. Patel, M. D. Mali and S. K. Patel, “Bernthsen synthesis, antimicrobial activities and cytotoxicity of acridine derivatives”, Bioorg. Med. Chem. Lett., 20, 6324-6326, 2010.
  7. M. D. Braccio, G. Grossi, G. Roma, M. G. Signorello and G. Leoncini, “Synthesis and in vitro inhibitory activity on human platelet aggregation of novel properly substituted 4-(1-piperazinyl)coumarins”, Eur. J. Med. Chem., 39, 397-409, 2004.
  8. X. Zhou, X. B. Wang, T. Wang and L. Y. Kong, “Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues”, Bioorg. Med. Chem., 16, 8011-8021, 2008. doi: 10.1016/j.b mc2008.07.068
  9. F. E. Ahmad, G. Allam, S. A. A. Abdelaziz, A. A. Hamid and I. A. Maghrabi, “Design, synthesis, anti-schistosomal activity and molecular docking of novel 8-hydroxyquinoline-5-sufonyl 1,4-diazepine derivatives”, Bioorg. Med. Chem., 46, 17-25, 2013. doi: 10.1016/j.bioorg.2012.10.003
  10. T. K. Joanna, H. Elzbieta, H. Kruszewska, W. Irena and D. Maciejewska, “Synthesis and pharmacological activity of O-aminoalkyl derivatives of 7-hydroxycoumarin”, Eur. J. Med. Chem., 46, 2252-2263, 2011. doi:10.1016/j.ejmech.2011.03.006
  11. M. Basanagouda, K. Shivashankar, M. V. Kulkarni, V. P. Rasal, H. Patel, S. S. Mutha and A. A. Mohite, “Synhesis and antimicrobial studies on novel sulfonamides containing 4-azidomethyl coumarin”, Eur. J. Med. Chem., 45, 1151–1157, 2010.
  12. G. S. Hassan and G. A. Soliman, “Design, synthesis and antiulcerogenic effect of some of furo-salicylic acid derivatives on acetic acid-induced ulcerative colitis”, Eur. J. Med. Chem., 45, 4104-4112, 2010. doi: 10.1016/j.ejmech.2010.05.071
  13. L. A. Shastri, K. Shivashankar and M. V. Kulkarni, “The synthesis of pyrrole biscoumarins, new structures for fluorescent probes”, Tetrahedron Lett., 48, 7215–7217, 2007. doi:10.1016/j.tetlet.2007.07.189.
  14. K. Shivashankar, M. V. Kulkarni, L. A. Shastri, V. P. Rasal and S. V. Rajendra, “The Synthesis and biological evaluation of regioisomeric benzothiazolylcoumarins”, Phosphorus, Sulfur, and Silicon, 181, 2187–2200, 2006. doi:10.1080/10426500600614550
  15. K. Shivashankar, L. A. Shastri, M. V. Kulkarni, V. P. Rasal and D. M. Saindane, “Multi-component reactions of formyl-4-aryloxymethylcoumarins under microwave irradiation”, J. Indian Chem. Soc., 86, 265-271, 2009.
  16. K. Shivashankar, L. A. Shastri, M. V. Kulkarni, V. P. Rasal and D. M. Saindane, “Halogenated 4-aryloxymethylcoumarins as potent antimicrobial agents”, J. Indian Chem. Soc., 85, 1163-1168, 2008.
  17. N. B. Yaragatti, M. V. Kulkarni, M. D. Ghate, S. S. Hebbar and G. R. Hegde, “Synthesis and biological evaluation of some new coumarinyl thiazolopyrimidinones”, J. Sulfur. Chem., 31, 123-133, 2010. doi:10.1080/17415990903569544
  18. K. Shivashankar, L. A. Shastri, M. V. Kulkarni, V. P. Rasal and S. V. Rajendra, “Synthetic and biological studies on 4-aryloxymethylcoumarinylthiazolidinones”, Phosphorus, Sulfur, and Silicon, 183, 56-68, 2008. doi:10.1080/10426500701555801
  19. N. B. Yaragatti and M. V. Kulkarni, “Synthesis of novel mercury heterocycles”, Polyhedron. 29, 2857-2861, 2010. doi:10.1016/j.poly.2010.07.010.
  20. Burger and G.E. Ulloyt, “Analgesic studies. β-Ethyl and β-isopropyl amine derivative of pyridine and thiazole”, J. Org. Chem., 12, 342-355, 1947.
  21. H. Revankar, M. V. Kulkarni and G. N. Anil kumar, “Crystal structure of 6-methyl-4-[(quinolin-8-yloxy)methyl]-2H-chromen-2-one”, X-ray Structure Analysis Online., 29, 5-7, 2013.
  22. I. Dhamija, Nitesh Kumar, S.N. Manjula, V. Parihar, M. Manjunath Setty and K.S.R. Pai. “Preliminary evaluation of in vitro cytotoxicity and in vivo antitumor activity of Premna herbacea Roxb. in Ehrlich ascites carcinoma model and Dalton’s lymphoma ascites model”, Exp. Toxicol. Pathol., 65, 235-242, 2013. doi:10.1016/j.etp.2011.08.009.