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Efficient Continuous-Flow Synthesis and Evaluation of Anticancer Activity of Novel Quinoline–Pyrazoline Derivatives

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Abstract

An efficient and simple continuous-flow synthetic protocol for novel quinoline-tethered pyrazoline derivatives, which involves condensation of 2-chloroquinoline-3-carbaldehydewith arylmethyl ketones followed by cyclisation with phenyl hydrazine, was developed. The newly synthesized pyrazolines were characterized by IR, 1H and 13C NMR spectroscopy, mass spectrometry, and elemental analysis and tested for anticancer activity against A375 (melanoma), MCF7 (breast), and HT-29 (colon) cell lines. Some of the newly synthesized derivatives showed a higher activity than the control drug Doxorubicin.

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REFERENCES

  1. Ashok, D., Ganesh, A., Ravi, S., Vijaya Lakshmi, B., and Ramesh, B., Russ. J. Gen. Chem., 2014, vol. 84, p. 2248. https://doi.org/10.1134/S1070363214110346

    Article  CAS  Google Scholar 

  2. Bansal, E., Srivastava, V.K., and Kumar, A., Eur. J. Med. Chem., 2001, vol. 36, p. 81. https://doi.org/10.1016/S0223-5234(00)01179-X

    Article  CAS  PubMed  Google Scholar 

  3. Gokhan-Kelekci, N., Yabanoglu, S., Kupeli, E., Salgin, U., Ozgen, O., Ucar, G., Yesilada, E., Kendi, E., Yesilade, A., and Bilgin, A.A., Bioorg. Med. Chem., 2007, vol. 15, p. 5775. https://doi.org/10.1016/j.bmc.2007.06.004

    Article  CAS  PubMed  Google Scholar 

  4. Lange, J.H.M., Coolen, K.A.C., Herman, H., Stuivenberg, V., Dijksman, J.A.R., Herremans, A.H.J., Ronken, E., Keizer, H.G., Tipker, K.K., McCreary, A.C., Veerman, W., Wals, H.C., Stork, B., Verveer, P.C., Den Hartog, A.P., De Jong, N.M.J., Adolfs, T.J.P., Hoogendoorn, J., and Kruse, C.G., J. Med. Chem., 2004, vol. 47, p. 627. https://doi.org/10.1021/jm031019q

    Article  CAS  PubMed  Google Scholar 

  5. Jeong, T.S., Kim, K.S., Kim, J.R., Cho, K.H., Lee, S., and Lee, W., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 2719. https://doi.org/10.1016/j.bmcl.2004.03.072

    Article  CAS  PubMed  Google Scholar 

  6. Abo-Ghalia, M. and Amr, A., Amino Acids, 2004, vol. 26, p. 283. https://doi.org/10.1007/s00726-003-0042-8

    Article  CAS  PubMed  Google Scholar 

  7. Manna, F., Chimenti, F., Fioravanti, R., Bolasco, A., Secci, D., Chimenti, P., Ferlinib, C., and Scambia, G., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 4632. https://doi.org/10.1016/j.bmcl.2005.05.067

    Article  CAS  PubMed  Google Scholar 

  8. Palaska, E., Aytemir, M., Uzbay, I.T., and Erol, D., Eur. J. Med. Chem., 2001, vol. 36, p. 539. https://doi.org/10.1016/S0223-5234(01)01243-0

    Article  CAS  PubMed  Google Scholar 

  9. Hayat, F., Salahuddin, S., Umar, S., and Azam, A., Eur. J. Med. Chem., 2010, vol. 45, p. 4669. https://doi.org/10.1016/j.ejmech.2010.07.028

    Article  CAS  PubMed  Google Scholar 

  10. Gembus, V., Furmand, C., Millet, R., Mansouri, R., Chavatte, P., Levacher, V., and Briere, J.F., Eur. J. Med. Chem., 2012, vol. 58, p. 396. https://doi.org/10.1016/j.ejmech.2012.10.031

    Article  CAS  PubMed  Google Scholar 

  11. Jainey, P.J. and Bhat, I.K., J. Young Pharm., 2012, vol. 4, p. 82. https://doi.org/10.4103/0975-1483.96621

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Puig-Basagoiti, F., Tilgner, M., Forshey, B.M., Philpott, S.M., Espina, N.G., Wentworth, D.E., Goebel, S.J., Masters, P.S., Falgout, B., Ren, P., Ferguson, D.M., and Shi, P.-Y., Antimicrob. Agents Chemother., 2006, vol. 50, p. 1320. https://doi.org/10.1128/AAC.50.4.1320-1329.2006

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Ali, M.A., Shaharyar, M., Siddiqui, A.A., Sriram, D., Yogeeswari, P., and Clercq, E.D., Acta Pol. Pharm. Drug Res., 2007, vol. 63, p. 423.

    Google Scholar 

  14. Zsoldos-Mady, V., Ozohanics, O., Csampai, A., Kudar, V., Frigyes, D., and Sohar, P., J. Organomet. Chem., 2009, vol. 694, p. 4185. https://doi.org/10.1016/j.jorganchem.2009.09.007

    Article  CAS  Google Scholar 

  15. Brune, K., Acute Pain, 1997, vol. 1, p. 33. https://doi.org/10.1016/S1366-0071(97)80033-2

    Article  CAS  Google Scholar 

  16. Wong, A., Sibbald, A., Ferrero, F., Plager, M., Santolaya, M.E., Escobar, A.M., Campos, S., Barragán, S., González, M.D.L., Kesselring, G.L., and Pediatric, F., Clin. Pediatr., 2001, vol. 40, p. 313. https://doi.org/10.1177/000992280104000602

    Article  CAS  Google Scholar 

  17. Uwai, Y., Saito, H., and Inui, K., Eur. J. Pharmacol., 2000, vol. 409, p. 31. https://doi.org/10.1016/S0014-2999(00)00837-2

    Article  CAS  PubMed  Google Scholar 

  18. Matthews, N.S., Peck, K.E., Taylor, T.S., and Mealey, K.L., Am. J. Vet. Res., 2001, vol. 62, p. 673. https://doi.org/10.2460/ajvr.2001.62.673

    Article  CAS  PubMed  Google Scholar 

  19. Underwood, M., BMJ, 2006, vol. 332, p. 1315. https://doi.org/10.1136/bmj.332.7553.1315

    Article  PubMed  PubMed Central  Google Scholar 

  20. Rasha, M.A., Rabah, A.T.S., Amira, M.E., Ghada, H.A., and Dalal, A.A., J. Am. Sci., 2016, vol. 12, p. 10. https://doi.org/10.7537/marsjas120516.02

    Article  Google Scholar 

  21. Jain, S., Chandra, V., Kumar Jain, P., Pathak, K., Pathak, D., and Vaidya, A., Arab. J. Chem., 2019, vol. 12, p. 4920. https://doi.org/10.1016/j.arabjc.2016.10.009

    Article  CAS  Google Scholar 

  22. Abid, M. and Azam, A., Eur. J. Med. Chem., 2005, vol. 40, p. 935. https://doi.org/10.1016/j.ejmech.2005.03.015

    Article  CAS  PubMed  Google Scholar 

  23. Zhang, Z., Wang, D., Wei, Y., and Shi, M., Chem. Comm., 2012, vol. 48, p. 9607. https://doi.org/10.1039/C2CC35135H

    Article  CAS  PubMed  Google Scholar 

  24. Azarifar, D. and Maleki, B., J. Heterocycl. Chem., 2005, vol. 42, p. 157. https://doi.org/10.1002/jhet.5570420125

    Article  CAS  Google Scholar 

  25. Sreenu, P. and Rao, V.R., Synth. Comm., 2014, vol. 44, p. 583. https://doi.org/10.1080/00397911.2013.796522

    Article  CAS  Google Scholar 

  26. Kodide, S.K., Siddaiah, V., Lilakar, J.D., and Ganesh, A., Chem. Data Collect., 2020, vol. 28, 100457. https://doi.org/10.1016/j.cdc.2020.100457

  27. Kodide, S.K., Sandeep, M., Siddaiah, V., Lilakar, J.D., and Ganesh, A., Chem. Data Collect., 2020, vol. 29, 100488. https://doi.org/10.1016/j.cdc.2020.100488

  28. Ashok, D., Ganesh, A., Vijaya Lakshmi, B., and Ravi, S., Russ. J. Gen. Chem., 2014, vol. 84, p. 1237. https://doi.org/10.1134/S1070363214060309

    Article  CAS  Google Scholar 

  29. Pujari, V.K., Vinnakota, S., Kakarla, R.K., Maroju, S., and Ganesh, A., Russ. J. Org. Chem., 2019, vol. 55, p. 1772. https://doi.org/10.1134/S1070428019110204

    Article  CAS  Google Scholar 

  30. Pujari, V.K., Vinnakota, S., Kakarla, R.K., Maroju, S., Ganesh, A., and Pervaram, S., Russ. J. Gen. Chem., 2018, vol. 88, p. 1502. https://doi.org/10.1134/S1070363218070241

    Article  CAS  Google Scholar 

  31. Santhosh Kumar, K., Mohanty, S., Reddy, G.P., Siddaiah, V., Lilakar, J.D. and Goud, G.L., Russ. J. Gen. Chem., 2019, vol. 89, p. 1221. https://doi.org/10.1134/S1070363219060197

    Article  Google Scholar 

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Kumar, K.S., Siddaiah, V., Lilakar, J.D. et al. Efficient Continuous-Flow Synthesis and Evaluation of Anticancer Activity of Novel Quinoline–Pyrazoline Derivatives. Russ J Org Chem 56, 2014–2021 (2020). https://doi.org/10.1134/S1070428020110160

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