Journal of Chemical Crystallography

, Volume 38, Issue 5, pp 381–386

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

  • R. K. Somvanshi
  • R. Subashini
  • V. Dhanasekaran
  • G. Arulprakash
  • S. N. Das
  • S. Dey
Original Paper

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.

Graphical Abstract

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

Keywords

Aryl amine Malonic acid 2,4-Dichloro-6-methylquinoline Crystal structure Flow cytometry Apoptosis 

References

  1. 1.
    Sui Z, Altom J, Nguyen VN, Fernandez J, Bernstein JI, Hiliard JJ, Barrett JF, Podpogar BL, Ohemeng KA (1998) Bioorg Med Chem 6:735–742CrossRefGoogle Scholar
  2. 2.
    Michael JP (1997) Nat Prod Rep 14:605–618CrossRefGoogle Scholar
  3. 3.
    Campbell SF, Hardstone JD, Palmer MJ (1988) J Med Chem 31:1031–1035CrossRefGoogle Scholar
  4. 4.
    Forgsren A, Bredberg A, Riesback K (1989) Rev Infect Dis 11:S1382–S1389Google Scholar
  5. 5.
    Pu L, Amoscato AA, Bier ME, Lazo JS (2003) J Biol Chem 277:46877–46885CrossRefGoogle Scholar
  6. 6.
    El-Rayes BF, Grignon R, Aslam N, Aranha O, Sarkar FH (2002) Int J Oncol 21:207–211Google Scholar
  7. 7.
    Badawey E-S, Kappe T (1997) Eur J Med Chem 32:815–822CrossRefGoogle Scholar
  8. 8.
    Baker WR, Cai S, Dimitroff M, Fang L, Huh KK, Ryckman DR, Shang X, Shawar RM, Therrien JH (2004) J Med Chem 47:4693–4709CrossRefGoogle Scholar
  9. 9.
    Riodan JR, Ling V (1985) Pharmacol Ther 28:51–53CrossRefGoogle Scholar
  10. 10.
    Mikihiko N, Naito M, Matsuba Y, Sato S, Hirata H, Tsuruo T (2002) Clin Cancer Res 8:582–588Google Scholar
  11. 11.
    Katritzky AR, Rees CW (eds) (1984) Comprehensive heterocyclic chemistry. Pergamon Press, Oxford, 2ppGoogle Scholar
  12. 12.
    Katritzky AR, Rees CW, Scriven EFV (eds) (1996) Comprehensive heterocyclic chemistry. Elsevier, Oxford, 5ppGoogle Scholar
  13. 13.
    Monsandl T, Kappe CO, Flammang R, Wentrup C (1992) J Chem Commun 21:1571–1573Google Scholar
  14. 14.
    Meth-Cohn O (1993) Heterocycles 35:539–557CrossRefGoogle Scholar
  15. 15.
    Menasra H, Kedjadja A, Debache A, Rhouati S (2005) Synth Commun 35:2779–2788CrossRefGoogle Scholar
  16. 16.
    Kamakshi R, Reddy BSR (2007) Catal Commun 8:825–828CrossRefGoogle Scholar
  17. 17.
    Sheldrick GM (1997) SHELXS 97, a program for the determination of crystal structures. Anorganisch—Chemisches Institut der Universitat1997, Gottingen, GermanyGoogle Scholar
  18. 18.
    Sheldrick GM (1976) SHELXL 97, a program for the refinement of crystal structures. Anorganisch—Chemisches Institut der Universitat, Gottingen, GermanyGoogle Scholar
  19. 19.
    Cromer DT, Mann JB (1968) Acta Cryst A24:321–324Google Scholar
  20. 20.
    Stewart RF, Davidson ER, Simpson WT (1965) J Chem Phys 42:3175–3187CrossRefGoogle Scholar
  21. 21.
    Vermes I, Haanen C, Steffens-nakken H, Reutelingsperger C (1995) J Immunol Methods 184:39–51CrossRefGoogle Scholar
  22. 22.
    Desiderato R, Terry R, Freeman GR (1971) Acta Cryst B27:2443–2447Google Scholar
  23. 23.
    Palenik GJ (1964) Acta Cryst 17:687–695CrossRefGoogle Scholar
  24. 24.
    Palenik GJ (1964) Acta Cryst 17:696–700CrossRefGoogle Scholar
  25. 25.
    Palani K, Ponnuswamy A, Ponnuswamy MNG, Yathirajan HS, Prabhuswamy B, Raju CR, Nagaraja P, Shashikhant S (2004) Anal Sci 20:403–404CrossRefGoogle Scholar
  26. 26.
    Elsea SH, McGuirk PR, Gootz TD, Moynihan M, Osheroff N (1993) Antimicrob Agents Chemother 137:2179–2186Google Scholar
  27. 27.
    Dzieduszycka M, Bontemos-Gracz MM, Stefanska B, Martelli S, Piwkoska A, Arciemiuk M, Borowski E (2006) Bioorg Med Chem 14:2880–2886CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • R. K. Somvanshi
    • 1
  • R. Subashini
    • 2
  • V. Dhanasekaran
    • 2
  • G. Arulprakash
    • 2
  • S. N. Das
    • 3
  • S. Dey
    • 1
  1. 1.Department of BiophysicsAll India Institute of Medical SciencesNew DelhiIndia
  2. 2.Chemistry Division, School of Science and HumanitiesVellore Institute of TechnologyVelloreIndia
  3. 3.Department of BiotechnologyAll India Institute of Medical SciencesNew DelhiIndia

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