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Functionalization of 5-(4-alkoxybenzyl)-4-R-4H-1,2,4-triazole-3-thiols. Synthesis of novel DNA methylation inhibitors

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Abstract

Aminomethylation and cyanoethylation reactions of 5-(4-alkoxybenzyl)-4-methyl(phenyl, allyl)-4H-1,2,4-triazole-3-thiols have been investigated. According to NMR spectroscopy data, the reactions occur at the nitrogen atom Ν2. The effect of the synthesized compounds on cancer DNA methylation has been evaluated.

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References

  1. Zhou, C.H. and Wong, Y., Curr. J. Med. Chem., 2012, vol. 19, p. 239. doi 10.2174/092986712803414213

    Article  CAS  Google Scholar 

  2. He, R., Chen, Y.F., and Chen, Y.H., J. Med. Chem., 2010, vol. 53, p. 1347. doi 10.1021/jm901667k

    Article  CAS  Google Scholar 

  3. Dogdas, E., Tozkoparan, B., Kaynok, F.B., Eriksson, L., Kiipeli, E., Yesiloda, E., and Erten M., Arz.-Forsch. (Drug Res.), 2007, vol. 57, p. 196. doi 10.1055/s-0031-1296606

    CAS  Google Scholar 

  4. Ramasamy, K.S., Tam, R.C., Bard, J., and Averett, D.R., J. Med. Chem., 2000, vol. 43, p. 1019. doi 10.1021/jm9905514

    Article  CAS  Google Scholar 

  5. Hovsepyan, T.R., Melik-Ohanjanyan, R.G., Panosyan, G.A., Arsenyan, F.H., and Garibdzhanyan, B.T., Pharm. Chem. J., 2009, vol. 43, p. 645. doi 10.1007/s11094-010-0371-3

    Article  Google Scholar 

  6. Hovsepyan, T.R., Grboyan, S.V., Arsenyan, F.H., and Melik-Ohanjanyan, R.G., Pharm. Chem. J., 2011, vol. 45, no. 12, p. 705. doi 10.1007/511094-012-0706-3

    Article  Google Scholar 

  7. Hovsepyan, T.R., Dilanyan, S.V., Hakobyan, M.R., Minasyan, N.S., Paronikyan, R.V., and Melik-Ohanjanyan, R.G., Khim. Zh. Arm., 2016, vol. 69, nos. 1–2, p. 121.

    Google Scholar 

  8. Hovsepyan, T.R., Arsenyan, F.H., Nersesyan, L.E., Aharonyan, A.S., Danielyan, I.S., Paronikyan, R.V., and Melik-Ohanjanyan, R.G., Pharm. Chem. J., 2015, vol. 49, no. 4, p. 231. doi 10.1007/s11094-015-1261-5

    Article  CAS  Google Scholar 

  9. Avetisyan, A.Kh., Hovsepyan, T.R., Dzhagatspanyan, I.A., Hakobyan, N.E., Hakobyan, A.G., Sapondzhanyan, P.G., and Paronikyan, R.V., Khim.-Farm. Zh., 1978, vol. 12, no. 11, p. 40.

    CAS  Google Scholar 

  10. Romanov, G.A. and Vanyushin, B.F., Mol. Biol., 1980, vol. 14, no. 2, p. 356.

    Google Scholar 

  11. Vanyushin, B.F., Epigenetika. Genetika, 2006, vol. 42, no. 9, p. 1186.

    Google Scholar 

  12. Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv (Guidelines on the Preclinical Studies of Medicines), Mironov, A.N., Ed., Moscow: Meditsyna, 2012.

  13. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2010.

    Google Scholar 

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Authors and Affiliations

  1. A.L. Mnjoyan Institute of Fine Organic Chemistry, Scientific-Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    M. R. Hakobyan, T. R. Hovsepyan, L. E. Nersesyan, A. S. Agaronyan, I. S. Danielyan & R. V. Paronikyan

  2. Molecular Structure Research Center, Scientific-Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, Yerevan, Armenia

    N. S. Minasyan

Authors
  1. M. R. Hakobyan
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  2. T. R. Hovsepyan
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  3. L. E. Nersesyan
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  4. A. S. Agaronyan
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  5. I. S. Danielyan
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  6. R. V. Paronikyan
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  7. N. S. Minasyan
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Corresponding author

Correspondence to T. R. Hovsepyan.

Additional information

Original Russian Text © M.R. Hakobyan, T.R. Hovsepyan, L.E. Nersesyan, A.S. Agaronyan, I.S. Danielyan, R.V. Paronikyan, N.S. Minasyan, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 5, pp. 782–787.

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Hakobyan, M.R., Hovsepyan, T.R., Nersesyan, L.E. et al. Functionalization of 5-(4-alkoxybenzyl)-4-R-4H-1,2,4-triazole-3-thiols. Synthesis of novel DNA methylation inhibitors. Russ J Gen Chem 87, 973–978 (2017). https://doi.org/10.1134/S1070363217050140

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  • DOI: https://doi.org/10.1134/S1070363217050140

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