Russian Journal of General Chemistry

, Volume 79, Issue 12, pp 2767–2775 | Cite as

1-Hydrazinophthalazine based hydrazones and their transition metal complexes: Structure and biological activity

  • V. A. Kogan
  • S. I. Levchenkov
  • L. D. Popov
  • I. A. Shcherbakov
Article

Abstract

Structure, tautomeric rearrangements, acid-base properties and complex formation ability of 1-hydrazinophthalazine hydrazones and their coordination compounds with transition metals are considered. The main factors influencing the structure and physicochemical properties of the complexes, biological activity of phthalazine hydrazones and their complexes are discussed.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Kitaev, Yu.P. and Buzykin, B.I., Gidrazony (Hydrazones), Moscow: Nauka, 1974.Google Scholar
  2. 2.
    Dutta, R.L. and Hossain Md.M., J. Sci. Ind. Res., 1985, vol. 4, no. 12, p. 635.Google Scholar
  3. 3.
    Parpiev, N.A., Yusupov, V.G., Yakimovich, S.I., and Sharipov Kh.G., Atsilgidrazony i ikh kompleksy s perekhodnymi metallami (Cacylhydrasones and Their Transition Metal Complexes), Tashkent: Fan, 1988.Google Scholar
  4. 4.
    Kogan, V.A., Zelentsov, V.V., Larin, G.M., and Lukov, V.V., Kompleksy perekhodnykh metallov s gidrazonami. Fiziko-khimicheskie svoistva i stroenie (Complexes of Transition Metals with Hydrazones: Physicochemical Properties and Structure), Moscow: Nauka, 1990.Google Scholar
  5. 5.
    Zelenin, K.N., Khorseeva, L.A., and Alekseev, V.V., Khim. Farm. Zh., 1992, vol. 26, no. 5, p. 30.Google Scholar
  6. 6.
    Vicini, P., Incerty, M., Doytchinova, I.A., La Colla, P., Busonera, B., and Loddo, R., Eur. J. Med. Chem., 2006, vol. 48, no. 5, p. 624.CrossRefGoogle Scholar
  7. 7.
    Draey, J. and Tripod, I., Antihypertensive Agent., 1967, vol. 7, p. 223.Google Scholar
  8. 8.
    Mashkovskii, M.D., Lekarstvennye sredstva (Remedies), Moscow: Meditsina, 1972.Google Scholar
  9. 9.
    Segura-Pacheco, B., Trejo-Becerril, C., Perez-Cardenas, E., Taja-Chayeb, L., Mariscal, I., Chavez, A., Acuña, C., Salazar, A.M., Lizano, M., and Dueñas-Gonzalez, A., Clinical Cancer Research, 2003, vol. 9, no. 5, p. 1596.Google Scholar
  10. 10.
    Knowles, H.J., Tian, Y.M., Mole, D.R., and Harris, A.L., Circulation Research, 2004, vol. 95, p. 162.CrossRefGoogle Scholar
  11. 11.
    Sinha, B.K. and Motten, A.G., Biochem. Biophys. Res. Comm., 1982, vol. 105. no. 3, p. 1044.CrossRefGoogle Scholar
  12. 12.
    Zimmer, H. and Amer, A., Heterocycles, 1987, vol. 26, no. 5, p. 1177.CrossRefGoogle Scholar
  13. 13.
    Reece, P.A., Med. Res. Rev., 1981, vol. 1, no. 1, p. 73.CrossRefGoogle Scholar
  14. 14.
    Kaminskas, L.M., Pyke, S.M., and Burcham, P.C., Organic Biomolecular Chem., 2004, vol. 18, no. 2, p. 2578.CrossRefGoogle Scholar
  15. 15.
    Kaminskas, L.M., Pyke, S.M., and Burcham, P.C., J. Pharm. Exper. Therap., 2004, vol. 310, no. 3, p. 1003.CrossRefGoogle Scholar
  16. 16.
    Streeter, A.J. and Timbrell, J.A., Drug Metabolism and Disposition, 1983, vol. 11, no. 3, p. 184.Google Scholar
  17. 17.
    Schulbert, A.R., Arch. Int. Pharmacodyn., 1961, vol. 132, p. 1.Google Scholar
  18. 18.
    Urbaniy, T. and O’Connel, A., Anal. Chem., 1972, vol. 44, p. 565.CrossRefGoogle Scholar
  19. 19.
    Zak, B., Bartlett, W.E., Gilleran, T.G., and Lucas, G., J. Pharm. Sci., 1974, vol. 63, p. 225.CrossRefGoogle Scholar
  20. 20.
    Zak, B., Lukas, G., and Gilleran, T.G., Drug Metab. Dispos., 1977, vol. 5, p. 116.Google Scholar
  21. 21.
    Nakashima, K., Shimada, K., and Akiyama, S., Chem. Pharm. Bull., 1985, vol. 33, no. 4, p. 1515.Google Scholar
  22. 22.
    Semple, H.A., Tam, Y.K., Tin, S., and Courts, R.T., Pharmaceutical Research, 1988, vol. 5, no. 6, p. 383.CrossRefGoogle Scholar
  23. 23.
    Katritsky, A.R., Karelson, M., and Harris, P.J., Heterocycles, 1991, vol. 32, p. 329.CrossRefGoogle Scholar
  24. 24.
    Buzykin, B.I., Bystrykh, N.N., Stolyarov, A.P., Flegontov, S.A., Zverev, V.V., and Kitaev, Yu.P., Khim. Geterotsikl. Soedin., 1976, vol. 12, no. 3, p. 402.Google Scholar
  25. 25.
    Buzykin, B.I., Bystrykh, N.N., Stolyarov, A.P., Belova, L.V., and Kitaev, Yu.P., Khim. Geterotsikl. Soedin., 1976, vol. 12, no. 3, p. 402.Google Scholar
  26. 26.
    Bystrykh, N.N., Buzykin, B.I., Stolyarov, A.P., Flegontov, S.A., and Kitaev, Yu.P., Khim. Geterotsikl. Soedin., 1981, vol. 17, no. 5, p. 678.Google Scholar
  27. 27.
    Stassinopoulou, C., Tetrahedron, 1976, vol. 32. p. 1147.CrossRefGoogle Scholar
  28. 28.
    Butcher, R.J., Jasinski, J.P., Yathirajan, H.S., Vijesh, A.M., and Narayana, B., Acta Crystallogr., Sect. E: Struct. Rep. Online, 2007, vol. 63, p. 3674.CrossRefGoogle Scholar
  29. 29.
    Buyukgungor, O., Odabasoglu, M., Vijesh, A.M., and Yathirajan, H.S., Acta Crystallogr., Sect. E: Struct. Rep. Online, 2007, vol. 63, p. o4084.CrossRefGoogle Scholar
  30. 30.
    Giorgi, G., Ponticelli F., Chiasserini, L., and Pellerano, C., J. Chem. Soc., Perkin Trans. 2, 2000, p. 2259.Google Scholar
  31. 31.
    Sullivan, D.A. and Palenik, G.J., Inorg. Chem., 1977, vol. 16, p. 1127.CrossRefGoogle Scholar
  32. 32.
    Zhao, Y., Lin, Z., He, C., Wu, H., and Duan, C., Inorg. Chem., 2006, vol. 45, p. 10013.CrossRefGoogle Scholar
  33. 33.
    Attanasio, D., Dessy, G., and Fares, V., Inorg. Chim. Acta, 1985, vol. 104, p. 99.CrossRefGoogle Scholar
  34. 34.
    Mochon, M.C., Gallego, M.C., and Perez, A.G., Talanta, 1986, vol. 33, no. 7, p. 627.CrossRefGoogle Scholar
  35. 35.
    Shoukry, A.A. and Shoukri, M.A., Spectrochimica Acta, Part A, 2008, vol. 70, p. 686.CrossRefGoogle Scholar
  36. 36.
    Shcherbakov, I.N., Popov, L.D., Levchenkov, S.I., Morozov, A.N., and Kogan, V.A., Abstracts of Papers, IVth Int. Conf. on the New Technologies and Application of Modern Physico-Chemical Methods for the Study of Environment, Azov, 2007, p. 160.Google Scholar
  37. 37.
    Shcherbakov, I.N., Popov, L.D., Levchenkov, S.I., Morozov, A.N., and Kogan, V.A., Abstracts of Papers, IVth Int. Conf. on the New Technologies and Application of Modern Physico-Chemical Methods for the Study of Environment, Azov, 2007, p. 161.Google Scholar
  38. 38.
    Shcherbakov, I.N., Popov, L.D., Levchenkov, S.I., Morozov, A.N., Kogan, V.A., and Vikrishchuk, A.D., Zh. Obshch. Khim., 2008, vol. 78, no. 8, p. 1351.Google Scholar
  39. 39.
    Andrew, J.E. and Blake, A.B., J. Chem. Soc., A., 1969, p. 1408.Google Scholar
  40. 40.
    Tandon, S.S., Thompson, L.K., and Hynes, R.C., Inorg. Chem., 1992, vol. 31, p. 2210.CrossRefGoogle Scholar
  41. 41.
    Wen, T., Thompson, L.K., Lee, F.L., and Gabe, E.J., Inorg. Chem., 1988, vol. 27, p. 4190.CrossRefGoogle Scholar
  42. 42.
    Thompson, L.K., Mandal, S.K., Gabe, E.J., and Charland, J.-P., Chem. Commun., 1986, p. 1537.Google Scholar
  43. 43.
    Mandal, S.K., Thompson, L.K., Newlands, M.J., Charland, J.-P., and Gabe, E.J., Inorg. Chim. Acta, 1990, vol. 178, p. 169.CrossRefGoogle Scholar
  44. 44.
    Odashima, T., Yamada, M., Yonemory, N., and Ishii, H., Bull. Chem. Soc. Japan, 1987, vol. 60, no. 9, p. 3225.CrossRefGoogle Scholar
  45. 45.
    Paolucci, G., Stelluto, S., Sitran, S., Ajo, D., Benetollo, F., Polo, A., and Bombieri, G., Inorg. Chim. Acta, 1992, vol. 193, p. 57.CrossRefGoogle Scholar
  46. 46.
    Kogan, V.A. and Lukov, V.V., Koord. Khim., 1997, vol. 23, no. 1, p. 18.Google Scholar
  47. 47.
    Kogan, V.A. and Lukov, V.V., Koord. Khim., 1998, vol. 24, no. 3, p. 189.Google Scholar
  48. 48.
    Kahn, O., Magnetism of the Heterometallic Systems. Theoretical Approaches. Structure and Bonding, New York: Springer-Verlag, 1987, vol. 68, p. 89.Google Scholar
  49. 49.
    Popov, L.D., Shcherbakov, I.N., Levchenkov, S.I., Tupolova, Yu.P., Kogan, V.A., and Lukov, V.V., J. Coord. Chem., 2008, vol. 61, no. 3, p. 392.CrossRefGoogle Scholar
  50. 50.
    Antsyshkina, A.S., Porai-Koshits, M.A., Sadikov, G.G., Lukov, V.V., Kogan, V.A., and Levchenkov, S.I., Zh. Neorg. Khim., 1994, vol. 39, no. 6, p. 905.Google Scholar
  51. 51.
    Boilot, M.L., Kahn, O., O’Connor, C.J., Gouteron, J., Jeannien, S., and Jeannien, Y., J. Chem. Soc., Chem. Commun., 1985, no. 3, p. 178.Google Scholar
  52. 52.
    Mallah, T., Boilot, M.L., Kahn, O., Gouteron, J., Jeannien, S., and Jeannien, Y., Inorg. Chem., 1986, vol. 25, no. 17, p. 3058.CrossRefGoogle Scholar
  53. 53.
    O’Connor, C.J., Frmin, D.A., Pant, A.K., Ram Babu, B., and Stevens, E.D., Inorg. Chem., 1986, vol. 25, no. 14, p. 2300.CrossRefGoogle Scholar
  54. 54.
    Mallah, T., Boilot, M.L., Kahn, O., O’Connor, C.J., Gouteron, J., Jeannien, S., and Jeannien, Y., Inorg. Chem., 1987, vol. 26, no. 9, p. 1375.CrossRefGoogle Scholar
  55. 55.
    Sorrell, T.N., O’Connor, C.J., Anderson, O.P., and Reibenspies, J.H., J. Am. Chem. Soc., 1985, vol. 107, no. 14, p. 4199.CrossRefGoogle Scholar
  56. 56.
    Cairns, C.J. and Bush, D.H., Coord. Chem. Rev., 1986, vol. 69, p. 1.CrossRefGoogle Scholar
  57. 57.
    Kahn, O., Inorg. Chim. Acta, 1982, vol. 62, p. 3.CrossRefGoogle Scholar
  58. 58.
    Ridi, M., Lazzi, L., and Corti, P., Bull. Chim. Pharmac., 1968, vol. 107, no. 11, p. 667.Google Scholar
  59. 59.
    Razvi, M., Ramaligam, T., and Sattur, P.B., Ind. J. Chem., B, 1989, vol. 28, no. 8, p. 695.Google Scholar
  60. 60.
    Razvi, M., Ramaligam, T., and Sattur, P.B., Ind. J. Chem., B, 1989, vol. 28, no. 11, p. 987.Google Scholar
  61. 61.
    Albert, A., Selective Toxicity: the Physico-Chemical Basis of Therapy, London: Chapman and Hall, 1985.Google Scholar
  62. 62.
    John, E.K. and Grun, M.A., J. Med. Chem., 1990, vol. 33, no. 6, p. 1764.CrossRefGoogle Scholar
  63. 63.
    West, D.X., Liberta, A.E., Padhye, S.B., Chikate, R.C., Sonawane, P.B., Kumbhar, A.S., and Yerande, R.G., Coord. Chem. Rev., 1993, vol. 123, p. 49.CrossRefGoogle Scholar
  64. 64.
    Copper Proteins, Spiro, T.G., Ed., New York: Wiley Int., 1981.Google Scholar
  65. 65.
    Hughes, M.N., Inorganic Chemistry in Biological Systems, Chichester: Wiley, 1981.Google Scholar
  66. 66.
    Brill, A.S., Transition Metals in Biochemistry, Berlin: Springer Verlag, 1977.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • V. A. Kogan
    • 1
  • S. I. Levchenkov
    • 2
  • L. D. Popov
    • 1
  • I. A. Shcherbakov
    • 1
  1. 1.Southern Federal UniversityRostov-on-DonRussia
  2. 2.Southern Scientific Center of Russian Academy of SciencesRostov-on-DonRussia

Personalised recommendations