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1,3,4,6-tetracarbonyl systems. Part 8. Synthesis and antimicrobial activity of 2(5)-halogenated derivatives of 1,3,4,6-tetracarbonyl compounds

  • Molecular-Biological Problems of Drug Design and Mechanism of Drug Action
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Pharmaceutical Chemistry Journal Aims and scope

A series of 1,6-disubstituted 2,5-dibromohexan-1,3,4,6-tetraones and 2,2,5,5-tetrahalogenohexan-1,3,4,6-tetraones have been obtained by the treatment of 1,6-disubstituted hexane-1,3,4,6-tetraones with bromine and chlorine. Bromination of (4Z)-6-aryl-3,4-dihydroxy-6-oxohexa-2,4-dienamides led to (2Z,4E)-2-aminocarbonyl-6-aryl-5-bromo-3,4-dihydroxy-6-oxohexa-2,4-dienoates and 6-aryl-2,5-dibromo-3,4,6-trioxohexanamides in preparative yield. The proposed structures of the reaction products were confirmed by IR, UV, 1H and 13C NMR, and mass spectrometry. The bacteriostatic activity and acute toxicity of the synthesized compounds have been studied.

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References

  1. V. O. Kozminykh, N. M. Igidov, and E. N. Kozminykh, Zh. Org. Khim., 39(6), 912–917 (2003).

    Google Scholar 

  2. V. V. Novikova, Author's Abstract of a Candidate Dissertation in Pharmaceutical Sciences, Perm State Pharm. Acad., Perm (2003).

    Google Scholar 

  3. L. P. Yakhontov and R. G. Glushkov, in: Synthetic Drugs [in Russian], A. G. Natradze, ed., Meditsina, Moscow (1983), pp. 61–63.

    Google Scholar 

  4. M. D. Mashkovskii, Drugs (Handbook for Doctors) [in Russian], Meditsina, Moscow (1998), part. II, pp. 381–382.

    Google Scholar 

  5. S. G. Perevalov, Ya. V. Burgart, V. I. Saloutin, and O. N. Chupakhin, Usp. Khim., 70(11), 1039–1058 (2001).

    Google Scholar 

  6. V. O. Kozminykh and E. N. Kozminykh, Khim.-farm. Zh., 38(12), 10–20 (2004).

    Google Scholar 

  7. E. N. Kozminykh, A. O. Belyaev, E. S. Berezina, et al., Khim.-farm. Zh., 36(12), 9–11 (2002).

    Google Scholar 

  8. E. N. Kozminykh, A. O. Belyaev, V. O. Kozminykh, et al., Khim.-farm. Zh., 37(2), 21–24 (2003).

    Google Scholar 

  9. V. O. Kozminykh, A. O. Belyaev, E. N. Kozminykh, et al., Khim.-farm. Zh., 38(7), 22–26 (2004).

    Google Scholar 

  10. A. O. Belyaev, Author's Abstract of a Candidate Dissertation in Pharmaceutical Sciences, Kursk State Med. Univ., Kursk (2004).

    Google Scholar 

  11. V. O. Kozminykh, N. M. Igidov, E. N. Kozminykh, et al., Khim.-farm. Zh., 25(12), 43–47 (1991).

    CAS  Google Scholar 

  12. N. M. Igidov, E. N. Kozminykh, O. A. Sofina, et al., Khim. Geterotsikl. Soedin., No. 11, 1466–1475 (1999).

  13. T. M. Shironina, N. M. Igidov, E. N. Kozminykh, et al., Zh. Org. Khim., 37(10), 1555–1563 (2001).

    Google Scholar 

  14. V. O. Kozminykh, N. M. Igidov, and Yu. S. Kasatkina, Zh. Org. Khim., 37(11), 1604–1609 (2001).

    Google Scholar 

  15. O. Widman and E. Virgin, Chem. Ber., 42, 2794–2806 (1909); Beilsteins Handbuch der organischen Chemie, Vierte Auflage, Bd. 7, Berlin (1925), p. 895.

    Article  CAS  Google Scholar 

  16. Yu. S. Kasatkina, S. S. Shirinkina, N. M. Igidov, et al., “Prospects for development of natural sciences in graduate school,” in: Proceedings of an International Scientific Conference, Vol. 1, Organic Chemistry. Biologically Active Substances. New Materials [in Russian], Izd. Perm. Gos. Univ., Perm (2001), pp. 135–139; Ref. Zh. Khim., No. 5, 03.05, 19Zh114 (2003).

    Google Scholar 

  17. V. V. Novikova, T. F. Odegova, B. Ya. Syropyatov, et al., “Clinical microbiology and antimicrobial chemotherapy,” in: Vth International Conference MAKMAX “Antimicrobial Therapy,” Abstracts of Papers, Vol. 4, Appendix 1, Moscow (2002), p. 34.

  18. V. V. Novikova, T. F. Odegova, B. Ya. Syropyatov, et al., “Development, investigation, and marketing of a new pharmaceutical product,” in: Materials of the 58th Interregional Conference on Pharmacy and Pharmacology [in Russian], Izd. Pyatigor. Gos. Farm. Akad., Pyatogorsk (2003), pp. 341–343.

    Google Scholar 

  19. N. M. Igidov, V. O. Kozminykh, Yu. S. Kasatkina, et al., RF Pat. No. 2,229,473 (2004); Otkrytiya, No. 11, 46 (2004); Ref. Zh. Khim., No. 17, 04.17, 19O44P (2004).

  20. G. N. Pershin, Methods of Experimental Chemotherapy [in Russian], Izd. Med. Lit., Moscow (1971), pp. 100–117.

    Google Scholar 

  21. L. S. Strachunskii, Yu. B. Belousov, and S. N. Kozlov, eds., Practical Handbook of Anti-Infection Chemotherapy [in Russian], Izd. ZAO Borges, Moscow (2002), pp. 17, 73–78.

    Google Scholar 

  22. R. G. Glushkov, I. B. Levshin, N. B. Marchenko, et al., Khim.-farm. Zh., 18(9), 1048–1064 (1984).

    CAS  Google Scholar 

  23. G. A. Mokrushina, V. N. Charushin, and O. N. Chupakhin, Khim.-farm. Zh., 29(9), 5–19 (1995).

    CAS  Google Scholar 

  24. S. V. Yakovlev, Rus. Med. Zh., 6(22), 1449–1457 (1998).

    Google Scholar 

  25. E. N. Padeiskaya, Infekts. Antimikrob. Ther., 3(5), 150–155 (2001).

    Google Scholar 

  26. J. Y. Rex, T. J. Walsh, J. D. Sobel, et al., Clin. Infect. Dis., 30(4), 662–678 (2000).

    Article  PubMed  CAS  Google Scholar 

  27. S. E. Makhova, V. O. Kozminykh, N. M. Igidov, and S. S. Shirinkina, “Critical Problems in Surgery,” in: Materials of the 14th Interscholastic Symposium [in Russian], Izd. Mos. Med. Stomat. Inst., Moscow (1999), pp. 89–90.

    Google Scholar 

  28. V. B. Prozorovskii, M. P. Prozorovskii, and V. M. Demchenko, Farmakol. Toksikol., 41(4), 497–502 (1978).

    CAS  Google Scholar 

  29. I. V. Berezovskaya, Khim.-farm. Zh., 37(3), 32–34 (2003).

    Google Scholar 

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Authors and Affiliations

  1. Moscow State University of Technology and Management (Perm Division), Perm, Russia

    E. N. Kozminykh

  2. Stavropol State Medical Academy, Stavropol, Russia

    V. I. Goncharov

  3. Perm State Pedagogical University, Perm, Russia

    V. O. Kozminykh

Authors
  1. E. N. Kozminykh
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  2. V. I. Goncharov
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  3. V. O. Kozminykh
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 42, No. 9, pp. 18–24, September, 2008.

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Kozminykh, E.N., Goncharov, V.I. & Kozminykh, V.O. 1,3,4,6-tetracarbonyl systems. Part 8. Synthesis and antimicrobial activity of 2(5)-halogenated derivatives of 1,3,4,6-tetracarbonyl compounds. Pharm Chem J 42, 513–519 (2008). https://doi.org/10.1007/s11094-009-0172-8

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