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Reactivity and Anticancer Assessment of 4-Hydroxyquinoline Derivatives

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Abstract

Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate (1) exhibits a moderate cytotoxic activity against the MCF-7 mammary gland cancer cell line and HePG2 hepatocellular carcinoma cell line and a weak activity against the HCT-116 human colorectal carcinoma cell line. In order to enhance the cytotoxic activity of this compound, it was modified by changing the side-chain substituent and/or forming a new heterocyclic ring fused to the pyridine ring. Heating compound 1 with chloroacetyl chloride gave a mixture of two isomeric O-acylation products ethyl 4-(2-chloroacetoxy)-7-(trifluoromethyl)-quinoline-3-carboxylate and 3-chloro-8-(trifluoromethyl)-2H-pyrano[3,2-c]quinoline-2,4(3H)-dione, whereas the reaction with acetyl chloride in NaOH formed an N-acylation product 1-acetyl-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid. The reactions of compound 1 with urea, thiourea, hydrazine hydrate, hydroxylamine, o-phenylenediamine, phenyl isothiocyanate, and ethyl acetoacetate yielded the corresponding condensation products 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]urea, 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]thiourea, 7-(trifluoromethyl)-1,2-dihydropyrazolo[4,3-c]quinolin-3-one, 7-(trifluoromethyl)isoxazolo[4,5-c]quinolin-3(2H)-one, 3-(trifluoromethyl)-13H-benzo[2,3][1,4]diazepino[6,5-c]quinolin-7-ol, 3-phenyl-2-thioxo-8-(trifluoromethyl)-2,3-dihydro-4H-[1,3]oxazino[5,6-c]quinolin-4-one and ethyl 8-(trifluoromethyl)-2-methyl-4-oxo-4H-pyrano[3,2-c]quinolone 3-carboxylate, respectively. The structures of the synthesized compounds were confirmed by elemental analysis and spectral data.

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REFERENCES

  1. Markees, D.G., Dewey, V.C., and Kidder, G.W., J. Med. Chem., 1970, vol. 13, p. 324. https://doi.org/10.1021/jm00296a048

    Article  CAS  PubMed  Google Scholar 

  2. Cunico, W., Cechinel, C.A., Bonacorso, H.G., Martins, M.A., Zanatta, N., de Souza, M.V., Freitas, I.O., Soares, R.P., and Krettli, A.U., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 649. https://doi.org/10.1016/j.bmcl.2005.10.033

    Article  CAS  PubMed  Google Scholar 

  3. Kayirere, M., Mahmoud, A., Chevalier, J., Soyfer, J., Cremieux, A., and Barbe, J., Eur. J. Med. Chem., 1998, vol. 33, p. 55. https://doi.org/10.1016/S0223-5234(9980076-2)

    Article  CAS  Google Scholar 

  4. Ryu, C.K., Sun, Y.J., Shim, J.Y., You, H.J., Choi, K.U., and Lee, H., Arch. Pharm. Res., 2002, vol. 25, p. 795. https://doi.org/10.1007/BF02976994

    Article  CAS  PubMed  Google Scholar 

  5. Wise, R., Andrews, J.M., and Edwards, L.J., Antimicrob.Agents Chemother., 1983, vol. 23, p 559. https://doi.org/10.1128/AAC.23.4.559

  6. Liew, C., Schut, H.A., Chin, S.F., Pariza, M.W., and Dashwood, R.H., Carcinogenesis, 1995, vol. 16, p. 3037. https://doi.org/10.1093/carcin/16.12.3037

    Article  CAS  PubMed  Google Scholar 

  7. Eelderfield, R.C. and LeVon, E.F., J. Org. Chem., 1960, vol. 25, p. 1576. https://doi.org/10.1021/jo01079a027

    Article  Google Scholar 

  8. Jemal, A., Bray, F., Center, M. M., Ferly, J., Ward, E., and Forman, D., CA Cancer J. Clin., 2011, vol. 61, p. 69. https://doi.org/10.3322/caac.20107

    Article  PubMed  Google Scholar 

  9. Nitiss, J.L., Nat. Rev. Cancer, 2009, vol. 9, p. 338. https://doi.org/10.1038/nrc2607

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Zhou, J.L., Lu, Y.J., Ou, T.M., Zhou, J.M., Huang, Z.S., Zhu, X.F., Du, C.J., Bu, X.Z., Ma, L., Gu, Q., Li, Y.M., and Chan, A.S., J. Med. Chem., 2005, vol. 48, p. 7315. https://doi.org/10.1021/jm050041b

    Article  CAS  PubMed  Google Scholar 

  11. Carta, D., Bortolozzi, R., Hamel, E., Basso, G., Moro, S., Viola, G., and Ferlin, M.G., J. Med. Chem., 2015, vol. 58, p. 7991. https://doi.org/10.1021/acs.jmedchem.5b00805

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Hojjat-Farsangi, M., Int. J. Mol. Sci., 2014, vol. 15, p. 13768. https://doi.org/10.3390/ijms150813768

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Goel, H.L. and Mercurio, A.M., Nat. Rev. Cancer, 2013, vol. 13, p. 871. https://doi.org/10.1038/nrc3627

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Jamil, M.O., Hathaway, A., and Mehta, A., Curr. Oncol.Rep., 2015, vol. 17, p. 24. https://doi.org/10.1007/s11912-015-0451-3

    Article  CAS  PubMed  Google Scholar 

  15. LaMontagne, K.R., Butler, J., Borowski, V.B., Fuentes-Pesquera, A.R., Blevitt, J.M., Huang, S., Li, R., Connolly, P.J., and Greenberger, L.M., Angiogenesis, 2009, vol. 12, p. 287.

    Article  CAS  Google Scholar 

  16. Nakagawa, T., Matsushima, T., Kawano, S., Nakazawa, Y., Kato, Y., Adachi, Y., Abe, T., Semba, T., Yokoi, A., Matsui, J., Tsuruoka, A., and Funahashi, Y., CancerSci., 2014, vol. 105, p. 723. https://doi.org/10.1111/cas.12409

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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ACKNOWLEDGMENTS

All spectral measurements were carried out at the NMR laboratory of the Cairo University, and the NMR laboratory of the Faculty of Pharmacy, Ain Shams University, Egypt. The elemental analyses were obtained at the Central Lab, Cairo University, the Egypt Ministry of Defense Chemical Laboratories and the Micro Analytical Center, Ain Shams University. The authors would like to extend their sincere appreciation to all these institutions for cooperation in the present research.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Ain Shams University, 11566, Cairo, Egypt

    M. K. A. Regal & S. S. Shabana

  2. Basic Science Department, Higher Technological Institute, 44629, 10 th of Ramadan City, Egypt

    S. A. El-Metwally

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  1. M. K. A. Regal
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  2. S. S. Shabana
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  3. S. A. El-Metwally
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Correspondence to S. A. El-Metwally.

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Regal, M.K.A., Shabana, S.S. & El-Metwally, S.A. Reactivity and Anticancer Assessment of 4-Hydroxyquinoline Derivatives. Russ J Org Chem 56, 307–314 (2020). https://doi.org/10.1134/S1070428020020219

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