Imidazo(pyrimidine)annelated pyrido[3,2-d]pyrimidine. the synthesis and prediction of the biological activity / I.V.Dyachenko, R.I.Vaskevich, A.I.Vaskevich, M.V.Vovk

Authors

  • I. V. Dyachenko Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • R. I. Vaskevich Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • A. I. Vaskevich Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.16.907

Keywords:

pyridopyrimidines, electrophilic intramolecular cyclization, annеlation, polycyclic system, arylsulphenylchlorides, iodine, polyphosphoric acid, prediction of biological activity

Abstract

The literature references concerning the biological activity of pyrido[3,2-d]pyrimidines and condensed polycyclic systems based on them have been systematized and analyzed. The main methods of the synthesis of polyheterocycles containing the pyrido[3,2-d]pyrimidine moiety have been summarized. The synthetic potential of the electrophilic intramolecular cyclization as a convenient tool for the directed design of azolo- and azinoannelated pyrido[3,2-d]pyrimidine structures has been found. Regiochemistry of annеlation of the functional fragment of 2-allyl(cinnamyl)aminopyrido[3,2-d]pyrimidines has been studied under the action of three types of electrophilic reagents: iodine, polyphosphoric acid and arylsulphenylchlorides. The correlations have been found between the nature of substrate, electrophile, reaction conditions and the direction of intramolecular cyclization. It has been found that cyclization of 2-allyl(cinnamyl)aminopyrido[3,2-d]pyrimidines in the presence of polyphosphoric acid leads to linear forms of imidazopyridopyrimidinon, while in the conditions of iodocyclization and arylsulfenylation the tricyclic imidazoannelated pyridopyrimidines of the angular structure are mainly formed. Regioselectivity of annelation of the 2-cinnamyl moiety of aminopyrido[3,2-d]pyrimidine has been found. In particular, treatment of 2-cinnamylaminopyrido[3,2-d]pyrimidine with arylsulphenylchlorides or polyphosphoric acid results in formation of the linear tetrahydropyrido[3,2-d]pyrimidines, and iodocyclization leads to an angular isomer. The virtual screening of the compounds synthesized has shown that they may potentially exhibit a wide range of bioactivity.

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References

  1. Pat. US 2010/0204222 A1, 2010, http:// espacenet.com
  2. Pat. WO 2013/060881 A1, 2013, http:// espacenet.com
  3. Pat. US 2010/0204232 A1, 2010, http:// espacenet.com
  4. Pat. WO 94/05661, 1994, http:// espacenet.com
  5. Pat. WO 2010/002998 A1, 2010, http:// espacenet.com
  6. Pat. WO 2008/077649 A1, 2008, http:// espacenet.com
  7. Pat. WO 2006/135993 A1, 2006, http:// espacenet.com
  8. Pat. US 8338435 B2, 2012, http:// espacenet.com
  9. Pat. WO 2008/066664 A2, 2008, http:// espacenet.com
  10. Pat. WO 2008/024438 A2, 2008, http:// espacenet.com
  11. Pat. WO 2005/049613 A1, 2005, http:// espacenet.com
  12. Pat. WO 03/103575 A2, 2003, http:// espacenet.com
  13. Pat. US 2005/0182045 A1, 2005, http:// espacenet.com
  14. Pat. EP 1757594 A1, 2007, http:// espacenet.com
  15. Hanrahan P., Bell J., Bottomley G., Bradley S. Bioorg. Med. Chem. Let., 2012, Vol. 22, pp.2271.
  16. Pat. US 006060477A, 2000, http:// espacenet.com
  17. Wall M., Hoon Shim J., Benkovic S. J. J. Med. Chem, 1999, Vol. 42, No.
  18. , pp.3421. 18. Rewcastle G. W., Palmer B. D., Thompson A. M., Bridges A. G. J. Med. Chem., 1996, Vol. 39, pp.1823.
  19. Velthuisen E. J., Johns B. A., Gerondelis P., Yan Chen, Ming Li, Ke Mou Eur. J. Med. Chem., 2014, Vol. 83, pp.609.
  20. Bentabed-Ababsa G., Cheikh Sid Ely S. J. Org. Chem., 2010, Vol. 75, pp.839.
  21. Dyachenko I. V., Vas’kevich R. I., Vovk M. V. Zhurnal organichnoii ta farmatsevtichnoii khimiii – Journal of organic and pharmaceutical chemistry, 2016, Vol. 14, No.2 (54), pp.7-28.
  22. Vas’kevich R. I., Hripak S. M., Staninets V. I., Zborovsky Y. L., Chernega A. N. Russian Journal of Organic Chemistr., 2000, Vol. 7, pp.1091.
  23. Vas’kevich R. I., Hripak S. M., Staninets V. I., Zborovsky Y. L., Nesterenko A. M., Pyrogenko V. V. Ukrainskii khimicheskii zhurnal – Ukrainian chemical journal, 2000, Vol. 66, pp.47.
  24. Bentya A. V., Vas’kevich R. I., Bolbut A. V., Vovk M. V., Staninets V. I., Turov A. V., Rusanov E. B. Russian Journal of Organic Chemistry, 2008, Vol. 44, pp.1377.
  25. Bentya A. V., Vas’kevich R. I., Staninets V. I. Ukrainskii khimicheskii zhurnal – Ukrainian chemical journal, 2008, Vol. 74, pp.94.
  26. Bentya A. V., Vas’kevich R. I., Turov A. V., Rusanov E. B., Vovk M. V., Staninets V. I. Russian Journal of Organic Chemistry, 2011, Vol. 47, pp.1049.
  27. Dyachenko I. V., Vas’kevich R. I., Vovk M. V. Russian Journal of Organic Chemistry, 2014, Vol. 50, pp.270.
  28. Dyachenko I. V., Vas’kevich A. I., Vas’kevich R. I., Vovk M. V. Russian Journal of Organic Chemistry, 2014, Vol. 50, pp.874.
  29. Dyachenko I. V., Vas’kevich R. I., Vas’kevich A. I., Shishkina S. V., Vovk M. V. Russian Journal of Organic Chemistry, 2016, Vol. 52, pp.755.
  30. Vas’kevich R. I., Dyachenko I. V., Rusanov E. B., Vovk M. V. Russian Journal of Organic Chemistry, 2015, Vol. 51, pp.573.
  31. Vas’kevich A. I., Staninets V. I., Vovk M. V. Zhurnal organichnoi ta farmatsevtichnoi khimii – Journal of organic and pharmaceutical chemistry, 2012, Vol. 10, No.3 (39), pp.26-41.
  32. Zefirov N. S., Smith V. A., Bodrykov I. V., Krimer M. Z. Doklady Akademii Nauk SSSR, 1978, Vol. 240, No.4, pp.858-861.
  33. Vas’kevich A. I., Staninets V. I. Ukrainskii khimicheskii zhurnal – Ukrainian chemical journal, 2006, Vol. 72, No.3-4, pp.44.
  34. Vas’kevich A. I., Staninets V. I. Ukrainskii khimicheskii zhurnal – Ukrainian chemical journal, 2006, Vol. 72, No.11-12, pp.37.
  35. Poroykov V. V., Filimonov D. A., Stepanchikova A. V. Khimiko-pharmacevticheskii zhurnal – Chemical-pharmaceutical journal, 1996, Vol. 30, No.9, pp.20.
  36. Gloryozova T. A., Filimonov D. A., Lagunin A. A. Khimiko-pharmacevticheskii zhurnal – Chemical-pharmaceutical journal, 1998, Vol. 30, No.12, pp.32.
  37. Poroykov V. V., Filimonov D. A., Lagunin A. A. http://www.pharmaexpert.ru/passonline/downloads/articles/Lagunin_A-Abstract-Nov-16-2011.pdf.
  38. Filimonov D. A., Poroykov V. V. Oxford, 1996, pp.47.
  39. Borodyna Y. V., Filimonov D. A., Poroykov V. V. Khimiko-pharmacevticheskii zhurnal – Chemical-pharmaceutical journal, 1996, Vol. 30, No.12, pp.39.
  40. Kieft J. S. Trends in biochemical sciences, 2008, Vol. 33, No.6, pp.274.
  41. Thompson S. R. Trends in microbiology, 2012, Vol. 20, No.11, pp.558.
  42. Brown T. A. New York: Garland Science Publishing, 2007, P. 397.

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Published

2016-12-16

How to Cite

(1)
Dyachenko, I. V.; Vaskevich, R. I.; Vaskevich, A. I.; Vovk, M. V. Imidazo(pyrimidine)annelated pyrido[3,2-d]pyrimidine. The Synthesis and Prediction of the Biological Activity / I.V.Dyachenko, R.I.Vaskevich, A.I.Vaskevich, M.V.Vovk. J. Org. Pharm. Chem. 2016, 14, 48-57.

Issue

Vol. 14 No. 4(56) (2016)

Section

Original Researches

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