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Synthesis, Crystal Structure, Cytotoxic and Apoptotic Activity of 2,4-Dichloro-6-methylquinoline on Human Oral Carcinoma Cell Line

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Abstract

The present report describes the synthesis, IR spectra, 3-dimensional structure of the compound 2,4-dichloro-6-methylquinoline and evaluation of its anti-cancer activity using propidium iodide (PI) staining and annexin binding assay techniques. This derivative of quinoline was synthesized from the mixture of p-toluidine and malonic acid and synthesis has been achieved in a one-pot reaction from an aryl amine, malonic acid and phosphorous oxychloride. Crystallographic data reveals that the crystals belong to triclinic crystal system with space group P-1 with the unit cell dimensions of a = 7.14(1) Å, b = 11.53(1) Å, c = 11.97(1) Å and α = 90.18° (10), β = 106.31° (10), γ = 91.07° (10). The in vitro anti-cancer assay indicated that compound has cytotoxic and apoptotic activity on human oral squamous carcinoma (KB) cell line, thus it could be developed as a potent anti-cancer agent.

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Synthesis, Crystal Structure, Cytotoxic and Apoptotic Activity of 2,4-Dichloro-6-methylquinoline on Human Oral Carcinoma Cell Line

R. K. Somvanshia, R. Subashinib, V. Dhanasekaranb, G. Arulprakashb, S. N. Dasc, S. Deya

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References

  1. Sui Z, Altom J, Nguyen VN, Fernandez J, Bernstein JI, Hiliard JJ, Barrett JF, Podpogar BL, Ohemeng KA (1998) Bioorg Med Chem 6:735–742

    Article  CAS  Google Scholar 

  2. Michael JP (1997) Nat Prod Rep 14:605–618

    Article  CAS  Google Scholar 

  3. Campbell SF, Hardstone JD, Palmer MJ (1988) J Med Chem 31:1031–1035

    Article  CAS  Google Scholar 

  4. Forgsren A, Bredberg A, Riesback K (1989) Rev Infect Dis 11:S1382–S1389

    Google Scholar 

  5. Pu L, Amoscato AA, Bier ME, Lazo JS (2003) J Biol Chem 277:46877–46885

    Article  Google Scholar 

  6. El-Rayes BF, Grignon R, Aslam N, Aranha O, Sarkar FH (2002) Int J Oncol 21:207–211

    CAS  Google Scholar 

  7. Badawey E-S, Kappe T (1997) Eur J Med Chem 32:815–822

    Article  CAS  Google Scholar 

  8. Baker WR, Cai S, Dimitroff M, Fang L, Huh KK, Ryckman DR, Shang X, Shawar RM, Therrien JH (2004) J Med Chem 47:4693–4709

    Article  CAS  Google Scholar 

  9. Riodan JR, Ling V (1985) Pharmacol Ther 28:51–53

    Article  Google Scholar 

  10. Mikihiko N, Naito M, Matsuba Y, Sato S, Hirata H, Tsuruo T (2002) Clin Cancer Res 8:582–588

    Google Scholar 

  11. Katritzky AR, Rees CW (eds) (1984) Comprehensive heterocyclic chemistry. Pergamon Press, Oxford, 2pp

    Google Scholar 

  12. Katritzky AR, Rees CW, Scriven EFV (eds) (1996) Comprehensive heterocyclic chemistry. Elsevier, Oxford, 5pp

    Google Scholar 

  13. Monsandl T, Kappe CO, Flammang R, Wentrup C (1992) J Chem Commun 21:1571–1573

    Google Scholar 

  14. Meth-Cohn O (1993) Heterocycles 35:539–557

    Article  CAS  Google Scholar 

  15. Menasra H, Kedjadja A, Debache A, Rhouati S (2005) Synth Commun 35:2779–2788

    Article  CAS  Google Scholar 

  16. Kamakshi R, Reddy BSR (2007) Catal Commun 8:825–828

    Article  CAS  Google Scholar 

  17. Sheldrick GM (1997) SHELXS 97, a program for the determination of crystal structures. Anorganisch—Chemisches Institut der Universitat1997, Gottingen, Germany

    Google Scholar 

  18. Sheldrick GM (1976) SHELXL 97, a program for the refinement of crystal structures. Anorganisch—Chemisches Institut der Universitat, Gottingen, Germany

    Google Scholar 

  19. Cromer DT, Mann JB (1968) Acta Cryst A24:321–324

    Google Scholar 

  20. Stewart RF, Davidson ER, Simpson WT (1965) J Chem Phys 42:3175–3187

    Article  CAS  Google Scholar 

  21. Vermes I, Haanen C, Steffens-nakken H, Reutelingsperger C (1995) J Immunol Methods 184:39–51

    Article  CAS  Google Scholar 

  22. Desiderato R, Terry R, Freeman GR (1971) Acta Cryst B27:2443–2447

    Google Scholar 

  23. Palenik GJ (1964) Acta Cryst 17:687–695

    Article  CAS  Google Scholar 

  24. Palenik GJ (1964) Acta Cryst 17:696–700

    Article  CAS  Google Scholar 

  25. Palani K, Ponnuswamy A, Ponnuswamy MNG, Yathirajan HS, Prabhuswamy B, Raju CR, Nagaraja P, Shashikhant S (2004) Anal Sci 20:403–404

    Article  CAS  Google Scholar 

  26. Elsea SH, McGuirk PR, Gootz TD, Moynihan M, Osheroff N (1993) Antimicrob Agents Chemother 137:2179–2186

    Google Scholar 

  27. Dzieduszycka M, Bontemos-Gracz MM, Stefanska B, Martelli S, Piwkoska A, Arciemiuk M, Borowski E (2006) Bioorg Med Chem 14:2880–2886

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Authors acknowledge financial support from the Department of Science and Technology and Council of Scientific and Industrial Research, Government of India. Author thanks the service rendered by “Technology Business Incubator” at Vellore Institute of Technology, Vellore, “Sophisticated Instrumentation facility” at Indian Institute of Science, Bangalore and “Central Drug Research Institute”, Lucknow in recording FT-IR, 1H-NMR and Mass spectra.

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Somvanshi, R.K., Subashini, R., Dhanasekaran, V. et al. Synthesis, Crystal Structure, Cytotoxic and Apoptotic Activity of 2,4-Dichloro-6-methylquinoline on Human Oral Carcinoma Cell Line. J Chem Crystallogr 38, 381–386 (2008). https://doi.org/10.1007/s10870-007-9305-7

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