Skip to main content
Log in

β-hydroxy derivatives of six-membered nitrogenous heterocycles. Synthesis, inhibitory activity, and biological properties (Review)

  • Molecular-Biological Problems of the Creation of Drugs and Study of their Mechanism of Action
  • Published:
Pharmaceutical Chemistry Journal Aims and scope

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Literature cited

  1. N. M. Émanuél', in: Phenolic Compounds and Their Biological Functions [in Russian], Moscow (1968), p. 311.

  2. N. M. Emanuel, Q. Rev. Biophys.,9, 283 (1967).

    Google Scholar 

  3. E. B. Burlakova, A. V. Alesenko, E. M. Molochkina, et al., Bioantioxidants in Radiation Injury and Malignant Growths [in Russian], Moscow (1975).

  4. Yu. A. Vladimirov and A. I. Archakov, Peroxide Oxidation of Lipids in Biological Membranes [in Russian], Moscow (1972).

  5. V. V. Ershov, G. A. Nikiforov, and A. A. Volod'kin, Sterically Hindered Phenols [in Russian], Moscow (1972).

  6. Vitamins, No. 8. The Biochemistry of Vitamin E and Selenium [in Russian], Kiev (1975).

  7. A. R. Val'dman, G. Ya. Dubur, and Ya. Ya. Spruzh, Izv. Akad. Nauk Latv. SSR, No. 9, 43–61 (1977).

    Google Scholar 

  8. K. M. Dyumaev, L. D. Smirnov, and V. F. Bystrov, Izv. Akad. Nauk Latv. SSR, No. 5, 883–887 (1962).

    Google Scholar 

  9. L. D. Smirnov, S. I. Sholina, K. E. Kruglyakova, et al., Izv. Akad. Nauk Latv. SSR, Khim. Nauk, No. 5, 883–887 (1962).

    Google Scholar 

  10. K. M. Dyumaev and L. D. Smirnov, Usp. Khim., No. 10, 1788 (1975).

    Google Scholar 

  11. E. L. Hove and P. L. Harris, J. Nutr.,31, 699 (1946).

    Google Scholar 

  12. L. D. Smirnov, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., No. 1, 68 (1980).

    Google Scholar 

  13. N. M. Émanuél' and Yu. N. Lyaskovskaya, Inhibition of the Oxidation of Fats [in Russian], Moscow (1961).

  14. H. Leditschke, Chem. Ber.,85, 202 (1952).

    Google Scholar 

  15. H. Leditschke, Chem. Ber.,86., 123 (1953).

    Google Scholar 

  16. W. Gruber, Can. J. Chem.,31, 564 (1953).

    Google Scholar 

  17. Hiroshi Sugisawa and Kioshi Aso, Tohoku J. Agric. Res.,10, 137–149 (1959).

    Google Scholar 

  18. L. D. Smirnov, K. M. Dyumaev, N. I. Shuikin, et al., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 12, 2246–2247 (1962).

    Google Scholar 

  19. L. D. Smirnov, V. P. Lezina, et al., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 4, 752–754 (1953).

    Google Scholar 

  20. L. D. Smirnov, V. P. Lezina, et al., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 1, 198–200 (1965).

    Google Scholar 

  21. L. D. Smirnov, V. P. Lezina, et al., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 10, 1836–1845 (1965).

    Google Scholar 

  22. L. D. Smirnov, S. L. Orlova, V. P. Lezina, et al., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 8, 1816–1820 (1967).

    Google Scholar 

  23. L. D. Smirnov, V. S. Zhuravlev, et al., Khim. Geterotsikl. Soedin., No. 4, 518–520 (1973).

    Google Scholar 

  24. L. D. Smirnov, V. S. Zhuravlev, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 206–209 (1973).

    Google Scholar 

  25. H. Ledistchke, Arch. Pharm.,295, 323 (1962).

    Google Scholar 

  26. L. D. Smirnov, V. I. Kuz'min, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1845 (1970).

    Google Scholar 

  27. L. D. Smirnov, V. I. Kuz'min, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2784–2788 (1970).

    Google Scholar 

  28. L. D. Smirnov, V. I. Kuz'min, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1758–1763 (1970).

    Google Scholar 

  29. L. D. Smirnov, M. R. Avezov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 623–625 (1970).

    Google Scholar 

  30. L. D. Smirnov, M. R. Avezov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 626–627 (1970).

    Google Scholar 

  31. P. B. Terent'ev, M. Islam, et al., Vestn. Mosk. Gos. Univ., Ser. Khim., No. 2, 123 (1962).

    Google Scholar 

  32. H. S. Plas and H. J. Hertog, Chem. Weekblad,53, 560 (1957).

    Google Scholar 

  33. V. S. Zhuravlev, L. D. Smirnov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 222 (1976).

    Google Scholar 

  34. L. D. Smirnov, V. S. Zhuravlev, V. P. Lezina, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2801 (1973).

    Google Scholar 

  35. K. M. Dyumaev, L. D. Smirnov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2599 (1970).

    Google Scholar 

  36. L. D. Smirnov, V. S. Zhuravlev, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2106 (1974).

    Google Scholar 

  37. L. D. Smirnov, V. I. Kuz'min, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 861 (1973).

    Google Scholar 

  38. H. J. Hertog et al., Rec. Trav. Chem.,64, 700 (1950).

    Google Scholar 

  39. L. D. Smirnov, M. R. Avezov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2338 (1971).

    Google Scholar 

  40. S. Nakamura et al., Chem. Pharm. Rull. (Tokyo),16, 1466 (1968).

    Google Scholar 

  41. L. D. Smirnov, V. S. Zhuravlev, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1878 (1972).

    Google Scholar 

  42. L. D. Smirnov, V. S. Zhuravlev, et al., Khim. Geterotsikl. Soedin., No. 7, 958 (1974).

    Google Scholar 

  43. K. Krowicki and P. Nantka-Namirski, Rocz. Chem.,49, 1187 (1975).

    Google Scholar 

  44. K. Krowicki, Rocz. Chem.,50, 337 (1976).

    Google Scholar 

  45. K. Krowicki, Rocz. Chem.,50, 1785 (1976).

    Google Scholar 

  46. Pyridine and Its Derivatives, Part 3, New York (1962), p. 685.

  47. L. D. Smirnov, N. A. Andronova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2382 (1970).

    Google Scholar 

  48. L. D. Smirnov, N. A. Andronova, V. P. Lezina, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 456 (1971).

    Google Scholar 

  49. N. A. Andronova, L. D. Smirnov, V. P. Lezina, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 455 (1972).

    Google Scholar 

  50. L. D. Smirnov, N. A. Andronova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 457 (1972).

    Google Scholar 

  51. K. M. Dyumaev, E. P. Popova, et al., Khim. Geterotsikl. Soedin., No. 6, 382 (1975).

    Google Scholar 

  52. N. A. Andronova, L. D. Smirnov, et al., Izv. Akad. Nauk SSSR, Ser. Khim. (1971).

  53. N. A. Andronova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 502 (1972).

    Google Scholar 

  54. Suzuki Yasuyuki, Yakugaku Zasshi,81, 792 (1961).

    Google Scholar 

  55. P. B. Terent'ev, N. P. Lomakina, and A. N. Kost, Org. Mass Spectrom.,11, 281 (1976).

    Google Scholar 

  56. A. Dornow and H. Hell, Chem. Ber.,93, 1998 (1960).

    Google Scholar 

  57. V. F. Sedova and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 6, 827 (1979).

    Google Scholar 

  58. S. B. Gashev and L. D. Smirnov, Izv. Akad. Nauk SSSR, Ser. Khim, No. 3, 678 (1979).

    Google Scholar 

  59. S. B. Gashev, V. P. Lezina, and L. D. Smirnov, Khim. Geterotsikl. Soedin., No. 5, 681 (1980).

    Google Scholar 

  60. D. J. Brown, The Pyrimidines, New York (1970), p. 173.

  61. T. Sakuragi, J. Am. Oil. Chem. Soc.,36, 251 (1959).

    Google Scholar 

  62. T. Sakuragi and F. A. Kummerow, J. Am. Oil. Chem. Soc.,35, 401 (1958).

    Google Scholar 

  63. I. D. Tmenov and R. E. Lokhov, Zhivotnovodstvo, No. 2, 40 (1979).

    Google Scholar 

  64. N. A. Zakharova, V. I. Kul'min, K. I. Kruglyakova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1013 (1977).

    Google Scholar 

  65. N. G. Khrapova, Tr. Mosk. Ova. Ispyt. Prir.,32, 227 (1970).

    Google Scholar 

  66. N. G. Khrapova, “Chemiluminescent investigations of natural antioxidants and synthetic inhibitors,” Candidate's Dissertation, Moscow (1972).

  67. I. I. Sapezhinskii and E. G. Dontsova, Biofizika,23, 583 (1978).

    Google Scholar 

  68. I. I. Sapezhinskii, N. A. Gudkova, et al., Biofizika,25, 30 (1980).

    Google Scholar 

  69. V. M. Shiryaev, I. B. Fedorovich, et al., Biofizika,25, 439 (1980).

    Google Scholar 

  70. D. R. Minkhadzhidinova, V. I. Kuz'min, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2216–2218 (1981).

    Google Scholar 

  71. L. S. Varmanyan, A. I. Kazachenko, and N. M. Émanuél', Stud. Biophys.,83, 183.

  72. E. B. Burlakova, V. D. Gaintseva, et al., Dokl. Akad. Nauk SSSR,157, 979 (1964).

    Google Scholar 

  73. E. B. Burlakova, N. G. Khrapova, et al., Dokl. Akad. Nauk SSSR,169, 688 (1966).

    Google Scholar 

  74. L. D. Smirnov, V. I. Kuz'min, et al., in: The Synthesis, Properties, and Applications of Detoxifying Compounds [in Russian], Sverdlovsk (1971), p. 32.

  75. K. E. Kruglyakova, N. V. Nikolaeva, et al., Dokl. Akad. Nauk SSSR,157, 979 (1964).

    Google Scholar 

  76. L. A. Belova, E. B. Burlakova, et al., Radiobiologiya,7, 117 (1967).

    Google Scholar 

  77. E. B. Burlakova and N. M. Dzyuba, Dokl. Akad. Nauk SSSR,163, 1278 (1965).

    Google Scholar 

  78. E. B. Burlakova, S. A. Burobina, and N. G. Khrapova, Dokl. Akad. Nauk SSSR,200, 461 (1971).

    Google Scholar 

  79. N. P. Pal'mina, Radiobiologiya,12, 737 (1972).

    Google Scholar 

  80. L. N. Shishkina, N. P. Pal'mina, et al., Radiobiologiya,16, 230 (1976).

    Google Scholar 

  81. G. V. Arkhipova and E. B. Burlakova, Tr. Mosk. Ova. Ispyt. Prir.,52, 111 (1975).

    Google Scholar 

  82. G. V. Arkhipova and E. B. Burlakova, Radiobiologiya,14, 828 (1974).

    Google Scholar 

  83. E. B. Burlakova, N. M. Dzyuba, L. V. Slepukhina, et al., in: Problems in Tissue Radiosensitivity [in Russian], Alma Ata (1969), p. 125.

  84. L. V. Slepukhina, “Changes with inhibitors of free radical reactions,” Author's Abstract, Candidate's Dissertation, Moscow (1970).

  85. L. D. Smirnov, V. S. Zhuravlev, T. A. Klygul', et al., FAV, Naukova Dumka, No. 10, p. 59 (1978).

    Google Scholar 

  86. L. D. Smirnov, V. S. Zhuravlev, T. A. Klygul', et al., in: Synthesis and Mode of Action of Physiologically Active Compounds [in Russian], Odessa (1976), p. 143.

  87. P. P. Zagoskin, E. M. Khvatova, and L. D. Luk'yanov, Khim.-farm. Zh., No. 11, 53–56 (1977).

    Google Scholar 

  88. O. M. Panasenko, L. Ya. Gendel', et al., Izv. Akad. Nauk SSSR, Ser. Biol., No. 4, 607 (1981).

    Google Scholar 

  89. E. I. Shabarchin, K. E. Kruglyakova, et al., Dokl. Akad. Nauk SSSR,234, 490 (1977).

    Google Scholar 

  90. V. I. Shumakov, A. B. Tsypin, and L. D. Smirnov, in: All-Union Symposium on Phenolic Compounds. No. 3 [in Russian], Tbilisi (1976), p. 166.

    Google Scholar 

  91. A. B. Tsypin, L. D. Smirnov, et al., Patol. Fiziol., No. 5, 22 (1978).

    Google Scholar 

  92. L. K. Obukhova, A. B. Tsypin, et al., Izv. Akad. Nauk SSSR, Ser. Biol., No. 4, 548 (1979).

    Google Scholar 

  93. A. B. Tsypin and R. M. Kurginyan, in: Organ Transplantation in the Clinic and Experimentally, and Artificial Organs [in Russian], Moscow (1978), p. 209.

  94. I. P. Sadovnikova and L. K. Obukhova, in: Molecular and Cellular Ageing Mechanisms [in Russian], NII Gerontologii, Kiev (1981), p. 153.

    Google Scholar 

  95. N. A. Kubatiev and S. V. Andreev, Byull. Éksp. Biol., No. 5, 414 (1979).

    Google Scholar 

  96. V. P. Mishchenko, Yu. M. Gel'denberg, and T. V. Novosel'tseva, Vopr. Med. Khim., No. 6, 763 (1980).

    Google Scholar 

  97. A. N. Kleimenov, M. A. Rozenfel'd, E. B. Burlakova, et al., in: Injury to the Vascular Wall and Hemostasis [in Russian], Poltava (1981), p. 91.

  98. T. S. Shulyakovskaya, V. Yu. Arshinov, et al., Dokl. Akad. Nauk SSSR,254, 242 (1980).

    Google Scholar 

  99. E. B. Burlakova, in: Physicochemical Mechanisms of Malignant Neoplasms [in Russian], Moscow (1970), p. 9.

  100. F. Z. Meerson, L. M. Giber, et al., Dokl. Akad. Nauk SSSR,237, 977 (1977).

    Google Scholar 

  101. F. Z. Meerson, V. I. Pavlova, et al., Vopr. Med. Khim., No. 6, 827 (1980).

    Google Scholar 

  102. F. Z. Meerson, in: Adaptation, Stress, and Prophylaxis [in Russian], Moscow (1981), pp. 226–227.

  103. V. I. Kirpatovskii and L. D. Smirnov, in: Current Problems in Transplantology and Artificial Organs [in Russian], Moscow (1980), pp. 101–104.

  104. D. Harman, J. Gerontol.,11, 298 (1956).

    Google Scholar 

  105. A. Comfort, Gore I. Youhotsky, et al., Nature,229, 254 (1971).

    Google Scholar 

  106. N. M. Émanuél', L. K. Obukhova, L. D. Smirnov, et al., Dokl. Akad. Nauk SSSR,226, 961 (1976).

    Google Scholar 

  107. N. M. Émanuél, L. K. Obukhova, L. D. Smirnov, et al., Izv. Akad. Nauk SSSR, Ser. Biol., No. 1, 32 (1977).

    Google Scholar 

  108. L. K. Obukhova and L. D. Smirnov, in: Gerontology and Geriatrics [in Russian], Kiev (1975), p. 158.

  109. N. Sh. Nakaidze, L. K. Obukhova, L. D. Smirnov, et al., Izv. Akad. Nauk SSSR, Ser. Biol., No. 4, 632 (1978).

    Google Scholar 

  110. L. K. Obukhova, N. Sh. Nakaidze, et al., Exp. Gerontol.,14, 290 (1979).

    Google Scholar 

  111. N. P. Pal'mina, L. K. Obukhova, et al., Izv. Akad. Nauk SSSR, Ser. Biol., No. 2, 290 (1979).

    Google Scholar 

  112. L. K. Obukhova, T. L. Dubina, et al., Izv. Akad. Nauk SSSR, Ser. Biol., No. 4, 620 (1980).

    Google Scholar 

  113. S. T. Tsygankova, L. V. Slepukhina, and L. D. Smirnov, in: Immunodepressants in Allotransplantations [in Russian], Tashkent (1977), p. 145.

  114. A. B. Tsygin, M. M. Kapichnikov, et al., in: Immunodepressants in Allotransplantations [in Russian], Tashkent (1977), p. 146.

  115. V. S. Suskova, V. N. Petrosova, S. B. Gashev, et al., in: Immunodepressants in Allotransplantations [in Russian], Tashkent (1977), p. 138.

  116. D. Harman, M. L. Heidrick, and D. E. Eddy, J. Am. Geriat. Soc.,25, 400 (1977).

    Google Scholar 

  117. V. S. Suskova, V. N. Petrosova, E. N. Matsulenko, et al., Organ Transplantation in the Clinic and Experimentally, and Artificial Organs [in Russian], Moscow (1978), pp. 60–64.

  118. M. M. Kapichnikov, N. N. Dakhina, et al., Byull. Éksp. Biol., No. 1, 42 (1980).

    Google Scholar 

  119. V. N. Suskova, V. N. Petrosova, L. D. Smirnov, et al., Farmakol. Toksikol., No. 4, 413 (1979).

    Google Scholar 

  120. A. A. Suzdal'tseva, N. N. Dakhina, et al., in: All-Union Conference on Organ and Tissue Transplantation Proceedings [in Russian], Baku (1979), p. 151.

  121. V. S. Suskova, V. N. Petrosova, et al., in: All-Union Conference on Organ and Tissue Transplantation Proceedings [in Russian], Baku (1979), p. 142.

  122. L. M. Strigun and N. P. Konovalova, in: Current Problems in the Experimental Chemotherapy of Tumors [in Russian], Chernogolovka (1980), Part 2, pp. 54–58.

  123. E. N. Odintsova, Dokl. Akad. Nauk SSSR,176, 717–718 (1967).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 16, No. 4, pp. 412–428, April, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Smirnov, L.D., Dyumaev, K.M. β-hydroxy derivatives of six-membered nitrogenous heterocycles. Synthesis, inhibitory activity, and biological properties (Review). Pharm Chem J 16, 259–272 (1982). https://doi.org/10.1007/BF00763413

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00763413

Keywords

Navigation