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Synthesis of New Substituted 1,2,4-Triazoles and 1,3,4-Thiadiazoles and Their Effects on DNA Methylation Level

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Abstract

Continuing the search for biologically active compounds among functionally substituted azoles, new 1,2,4-triazole-3-thiols and 1,3,4-thiadiazoles derivatives bearing pharmacologically active carboxamide, hydroxyl or carboxyalkyl moieties, as well as N-acyclonucleoside, N-cyano- or carboxyethyl fragments were synthesized. Ability of some compounds obtained to inhibit the methylation of tumor DNA in vitro was revealed. The compound with the highest activity was selected for further in vivo studies.

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References

  1. Kushwaha, N., Kushwaha, S.K.S., and Rai, A.K., Int. J. Chem. Tech. Res., 2012, vol. 4, p. 517.

    CAS  Google Scholar 

  2. Shaker, R.M., Arkivoc, 2006, p. 59.

    Google Scholar 

  3. Gomha, S.M., Badry, M.G., and Abdolla, M.M., J. Heterocycl. Chem., 2016, vol. 53, p. 558. doi https://doi.org/10.1002/jhet.2417

    Article  CAS  Google Scholar 

  4. He, R., Chen, U.E., Chen, U.H., Ougolkov, A.V., Zhang, J.S., Saroy, D.N., Billadeai, D.D., and Kozikowski, A.P., J. Med. Chem., 2010, vol. 53, p. 6337. doi https://doi.org/10.1021/jm1002414

    Article  CAS  Google Scholar 

  5. Hamama, W.S., Gouda, M.A., Badr, M.H., and Zeorob, H.H., J. Heterocycl. Chem., 2013, vol. 50, p. 787. doi https://doi.org/10.1002/jhet.1569

    Article  CAS  Google Scholar 

  6. Kossentini, M., J. Heterocycl. Chem, 2015, vol. 52, p. 1769. doi https://doi.org/10.1002/jhet.2264

    Article  CAS  Google Scholar 

  7. Deshmukh, R., Karale, B., Akolkaz, H., and Kandhavane P., J. Heterocycl. Chem, 2017, vol. 54, p. 1355. doi https://doi.org/10.1002/jhet.2714

    Article  CAS  Google Scholar 

  8. Tan, C.X., Shi, Y.X., Weng, J.Q., Liu, X.H., Zhao, W.G., and Li B.J., J. Heterocycl. Chem., 2014, vol. 51, p. 90. doi https://doi.org/10.1002/jhet.1656

    Article  CAS  Google Scholar 

  9. Wang, Q.P., Zhang, J.Q., Damu, Guri, L.V., Wan Kun, Zhang, H.Z., and Zhou, Ch.H., Sci. China Chem., 2012, vol. 55, p. 2134. doi https://doi.org/10.1007/s11426-012-4602-1

    Article  CAS  Google Scholar 

  10. Witkowski, J.T., Robins, R.K., Sidwell, R.W., and Simon, L.N., J. Med. Chem., 1972, vol. 15, p. 1150. doi https://doi.org/10.1021/jm00281a014

    Article  CAS  PubMed  Google Scholar 

  11. Mi, J.H., Zhou, C.H., and Baix, X., Chin. J. Antibiot., 2007, vol. 32, p. 587.

    CAS  Google Scholar 

  12. Siddiqui, N. and Ahsan, W., Eur. J. Med. Chem., 2010, vol. 45, p. 1536. doi https://doi.org/10.1016/j.ejmech.2009.12.062

    Article  CAS  PubMed  Google Scholar 

  13. Gupta, A., Pandeya, S.N., Mishra, P., Kashaw, S.K., Jatav, Y., and Stables, J.P., Eur. J. Med. Chem., 2008, vol. 43, p. 135. doi https://doi.org/10.1016/j.ejmech.2007.02.004

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  15. 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, p. 231. doi https://doi.org/10.1007/s11094-015-1261-5

    Article  CAS  Google Scholar 

  16. Hakobyan, M.R., Hovsepyan, T.R., Nersesyan, L.E., Agaronyan, A.S., Danielyan, I.S., Paronikyan, R.V., and Minasyan, N.S., Russ. J. Gen. Chem., 2017, vol. 87, p. 973. doi https://doi.org/10.1134/S1070363217050140

    Article  CAS  Google Scholar 

  17. Hovsepyan, T.R., Dilanyan, S.V., Arsenyan, F.H., Muradyan, R.E., Minasyan, N.S., and Melik-Ohanjanyan, R.G., Pharm. Chem. J., 2018, vol. 52, p. 404. doi https://doi.org/10.1007/S11094-018-1830-5

    Article  CAS  Google Scholar 

  18. Hovsepyan, T.R., Avetisyan, A.Kh., Terdzhanyan, S.M., Kazaryan, E.V., Ter-Zakhaiyan, Yu.Z., Paronokyan, G.M., and Akopyan, L.G., Arm. Khim. Zh., 1990, vol. 43, p. 399.

    Google Scholar 

  19. Hovsepyan, T.R., Grboyan, S.V., Arsenyan, F.H., and Melik-Ohanjanyan, R.G., Pharm. Chem. J., 2011, vol. 45, p. 705. doi https://doi.org/10.1007/S11094-012-0706-3

    Article  CAS  Google Scholar 

  20. Hovsepyan, T.R., Hakobyan, M.R., Minasyan, N.S., and Melik-Ohanjanyan, R.G., Russ. J. Gen. Chem., 2016, vol. 86, p. 1306. doi https://doi.org/10.1134/S1070363216080119

    Article  CAS  Google Scholar 

  21. Schaeffer, H.J., Beauchamp, L., Miranda, P., Elion, G.B., Bauer, D.J., and Collins, P., Nature, 1978, vol. 272, p. 583. doi https://doi.org/10.1038/272583a0

    Article  CAS  PubMed  Google Scholar 

  22. Beauchamp, L.M., Dolmach, B.L., Schaeffer, H.J., Collins, P., Bauer, D.J., Keller, P.M., and Lyfe, J.A., J. Med. Chem, 1985, vol. 28, p. 982. doi https://doi.org/10.1021/jm00146a002

    Article  CAS  PubMed  Google Scholar 

  23. Robinson, B.J., J. Chem. Soc., 1963, p. 2417. doi https://doi.org/10.1039/JR9630002417

    Google Scholar 

  24. Melik-Ohanjanyan, R.G., Hovsepyan, T.R., Israelyan, S.G., Gukasyan, M.S., Karakhanyan, G.S., Panosyan, G.A., Tamazyan, R.A., and Ayvazyan, A.G., Russ. J. Org. Chem., 2015, vol. 51, p. 361. doi https://doi.org/10.1134/S1070428015030124

    Article  CAS  Google Scholar 

  25. Vanyushin, B.F., Masin, A.N., and Vasiliev, V.R., Biochim. Et Biophys. Acta, 1973, vol. 299, p. 397.

    Article  CAS  Google Scholar 

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Authors and Affiliations

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

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

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

    N. S. Minasyan

Authors
  1. T. R. Hovsepyan
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  2. M. R. Hakobyan
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  3. R. E. Muradyan
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  4. L. E. Nersesyan
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  5. A. S. Agaronyan
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  6. I. S. Danielyan
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  7. N. S. Minasyan
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Correspondence to T. R. Hovsepyan.

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Hovsepyan, T.R., Hakobyan, M.R., Muradyan, R.E. et al. Synthesis of New Substituted 1,2,4-Triazoles and 1,3,4-Thiadiazoles and Their Effects on DNA Methylation Level. Russ J Gen Chem 89, 673–679 (2019). https://doi.org/10.1134/S1070363219040066

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  • DOI: https://doi.org/10.1134/S1070363219040066

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