Skip to main content
SpringerLink
Log in

Dexoxadrol and its bioisosteres: structure, synthesis, and pharmacological activity

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The review addresses the complete anthology of the development and evolution of dexoxadrol derivatives comprising a class of highly efficient NMDA receptor antagonists. Main approaches to the synthesis of dexoxadrol and enantiomeric 1-(2-piperidyl)ethane-1,2-diols and their structural relationship with natural alkaloids from plants of the genera Conium and Astrogalus are considered. Data on biomolecular mechanisms of action of this type of compounds are summarized. The relationships between their chemical structure and biological activity are analyzed. Based on the revealed relationships, different pathways of targeted modifications of the chemical structures of dexoxadrol and its analogues are suggested, which would help in future in overcoming the limitations associated with this type of physiologically active compounds, such as insufficient affinity for the channel binding site of the NMDA-receptor ionophore complex, low hydrolytic stability, anticholinergic side effects, and the production of toxic metabolites. These modifications will make it possible to utilize in full measure the great pharmacological potential of this type of compounds.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. I. D. Henter, R. T. de Sousa, P. W. Gold, A. R. Brunoni, C. A. Zarate, Jr, R. Machado-Vieira, Expert Rev. Clin., 2017, 10, 153.

    Article  CAS  Google Scholar 

  2. D. Lodge, M. S. Mercier, Br. J. Pharmacol., 2015, 172, 4254.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. A. Nowacka, M. Borczyk, Eur. J. Pharmacol., 2019, 860, 172547.

    Article  CAS  PubMed  Google Scholar 

  4. A. Slomski, J. Am. Med. Ass., 2019, 322, 2375.

    Google Scholar 

  5. C. Andrade, J. Clin. Psychiatry, 2017, 78, e674.

    Article  PubMed  Google Scholar 

  6. P. Zanos, R. Moaddel, P. J. Morris, P. Georgiou, J. Fischell, G. I. Elmer, M. Alkondon, P. Yuan, H. J. Pribut, N. S. Singh, K. S. S. Dossou, Y. Fang, X. Huang, C. L. Mayo, I. W. Wainer, E. X. Albuquerque, S. M. Thompson, C. J. Thomas, C. A. Zarate, Jr, T. D. Gould, Nature, 2016, 533, 481.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. T. H. Pham, A. M. Gardier, Pharmacol. Ther., 2019, 199, 58.

    Article  CAS  PubMed  Google Scholar 

  8. B. Pochwat, A. Palucha-Poniewiera, B. Szewczyk, A. Pilc, G. Nowak, Expert Opin. Investig. Drugs, 2014, 23, 1457.

    Article  CAS  Google Scholar 

  9. B. Pochwat, A. Palucha-Poniewiera, B. Szewczyk, Expert Rev. Neurother., 2019, 67, 1.

    Google Scholar 

  10. J. Kornhuber, C. G. Parsons, S. Hartmann, W. Retz, S. Kamolz, J. Thome, P. Riederer, J. Neural Transm., 1995, 102, 237.

    Article  CAS  Google Scholar 

  11. BE Pat. 628167; https://worldwide.espacenet.com.

  12. J. Hidalgo, J. Gallin, A. Williams, C. R. Thompson, Pharmacologist, 1961, 3, 69.

    Google Scholar 

  13. T. P. Pruss, J. Hidalgo, C. R. Thompson, Proc. West. Pharm. Soc., 1963, 6, 40.

    CAS  Google Scholar 

  14. J. Hidalgo, C. R. Thompson, Proc. Soc. Exp. Biol. Med., 1963, 114, 92.

    Article  CAS  PubMed  Google Scholar 

  15. J. Hidalgo, C. R. Thompson, Arch. Int. Pharmacodyn., 1965, 105, 153.

    Google Scholar 

  16. R. Tar & Chem. Corp., Ind. Eng. Chem. Res., 1960, 52, 55A.

    Google Scholar 

  17. US Pat. 2421714; https://worldwide.espacenet.com.

  18. F. F. Blicke, E. L. Schumann, J. Am. Chem. Soc., 1952, 74, 2613.

    Article  CAS  Google Scholar 

  19. W. R. Hardie, J. Hidalgo, I. F. Halverstandt, R. E. Allen, J. Med. Chem., 1966, 9, 127.

    Article  CAS  PubMed  Google Scholar 

  20. US Pat. 3262938; https://worldwide.espacenet.com.

  21. CA Pat. 785305; https://worldwide.espacenet.com.

  22. A. Thurkauf, K. C. Rice, A. E. Jacobson, M. V. Mattson, C. George, P. C. Zenk, R. L. Balster, E. L. May, F. Ivy Carroll, S. Wayne Mascarella, J. Med. Chem., 1988, 31, 2257.

    Article  CAS  PubMed  Google Scholar 

  23. A. Thurkauf, M. V. Mattson, P. N. Huguenin, K. C. Rice, A. E. Jacobson, FEBS Lett., 1988, 238, 369.

    Article  CAS  PubMed  Google Scholar 

  24. CA Pat. 900487; https://worldwide.espacenet.com.

  25. C. Bhat, Chemistry Open, 2015, 4, 192.

    CAS  PubMed  PubMed Central  Google Scholar 

  26. C. Bhat, S. T. Budge, S. G. Tilve, Synthesis, 2014, 46, 2551.

    Article  CAS  Google Scholar 

  27. G. Raju, K. Anitha, P. R. Krishna, Synlett, 2015, 26, 937.

    Article  CAS  Google Scholar 

  28. F. M. Cordero, C. Vurchio, A. Brandi, J. Org. Chem., 2016, 81, 1661.

    Article  CAS  PubMed  Google Scholar 

  29. F. M. Cordero, D. Giomi, A. Brandi, Curr. Top. Med. Chem., 2014, 14, 1294.

    Article  CAS  PubMed  Google Scholar 

  30. I. Pastuszak, R. J. Molyneux, L. F. James, A. D. Elbein, Biochemistry, 1990, 29, 1886.

    Article  CAS  PubMed  Google Scholar 

  31. B. Macchi, A. Minutolo, S. Grelli, F. Cardona, F. M. Cordero, A. Mastino, A. Brandi, Glycobiology, 2010, 20, 500.

    Article  CAS  PubMed  Google Scholar 

  32. A. Minutolo, S. Grelli, F. Marino-Merlo, F. M. Cordero, A. Brandi, B. Macchi, A. Mastino, Cell Death Dis., 2012, 3, e358.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. J. Mondal, A. Panigrahi, A. R. Khuda-Bukhsh, Pharmacogn. Mag., 2014, 10, S524.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  34. S. F. Kramer, G. L. Flynn, J. Pharm. Sci., 1972, 61, 1897.

    Article  Google Scholar 

  35. L. W. Brown, A. A. Forist, J. Pharm. Sci., 1973, 62, 1365.

    Article  CAS  PubMed  Google Scholar 

  36. S. Lee, B. T. Green, K. D. Welch, J. A. Plister, K. E. Panter, Chem. Res. Toxicol., 2008, 21, 2061.

    Article  CAS  PubMed  Google Scholar 

  37. US Pat. 2743277; https://worldwide.espacenet.com.

  38. US Pat. 2735851; https://worldwide.espacenet.com.

  39. Yu. I. Chumakov, Piridinovye osnovaniya [Pyridine Bases], Tekhnika, Kiev, 1965, 190 pp. (in Russian).

    Google Scholar 

  40. H. C. Haas, H. S. Kolesninski, N. W. Shuler, Polym. Lett., 1965, 3, 879.

    Article  CAS  Google Scholar 

  41. A. E. Jacobson, E. A. Harrison, Jr, M. V. Mattson, M. F. Rafferty, K. C. Rice, J. H. Woods, G. Winger, R. E. Solomon, R. A. Lessor, J. V. Silverton, J. Pharmacol. Exp. Ther., 1987, 243, 110.

    CAS  PubMed  Google Scholar 

  42. D. L. Klayman, A. l. Lin, J. M. Hoch, J. P. Scovill, C. Lambros, A. S. Dobek, J. Pharm. Sci., 1984, 73, 1763.

    Article  CAS  PubMed  Google Scholar 

  43. W. Sauermilch, Chem. Ber., 1957, 90, 833.

    Article  CAS  Google Scholar 

  44. W. Winker, Chem. Ber., 1948, 81, 256.

    Article  Google Scholar 

  45. Pat. RF 2334740; Byul. Izobret. [Inventor Bull.], 2008, No. 27 (in Russian).

  46. M. Imuta, K. Kawai, H. Ziffer, J. Org. Chem., 1980, 45, 3352.

    Article  CAS  Google Scholar 

  47. A. Thurkauf, M. V. Mattson, S. Richardson, S. Mirsadeghi, P. L. Ornstein, E. A. Harrison, K. C. Rice, A. E. Jacobson, J. A. Monn, J. Med. Chem., 1992, 35, 1323.

    Article  CAS  PubMed  Google Scholar 

  48. G. He, S. Zhang, W. A. Nack, R. Pearson, J. Rabb-Lynch, G. Chen, Org. Lett., 2014, 16, 6488.

    Article  CAS  PubMed  Google Scholar 

  49. A. Mikleušević, I. Primožič, T. Hrenar, B. Salopek-Sondi, L. Tang, M. M. Elenkov, Tetrahedron Asymmetry, 2016, 27, 930.

    Article  CAS  Google Scholar 

  50. M. B. Nawrozkij, E. B. Gorbunov, A. S. Babushkin, E. A. Ruchko, G. L. Rusinov, V. N. Charushin, I. A. Novakov, Macroheterocycles, 2014, 7, 18.

    Article  Google Scholar 

  51. R. Menasse, G. Klein, H. Erlenmeyer, Helv. Chim. Acta, 1955, 38, 1289.

    Article  CAS  Google Scholar 

  52. P. A. Bradley, R. J. Carroll, Y. C. Lecouturier, R. Moore, P. Noeureuil, B. Patel, J. Snow, S. Wheeler, Org. Proc. Res. Dev., 2010, 14, 1326.

    Article  CAS  Google Scholar 

  53. S. T. Liu, K. V. Reddy, R. Y. Lai, Tetrahedron, 2007, 63, 1821.

    Article  CAS  Google Scholar 

  54. K. Kloc, E. Kubicz, J. Mlkochowski, Heterocycles, 1984, 22, 2517.

    Article  CAS  Google Scholar 

  55. H. Toda, R. Imae, N. Itoh, Tetrahedron Asymmetry, 2012, 23, 1542.

    Article  CAS  Google Scholar 

  56. S. Bernasconi, F. Orsini, G. Sello, A. Colmegna, E. Galli, G. Bestetti, Tetrahedron Lett., 2000, 41, 9157.

    Article  CAS  Google Scholar 

  57. H. Lin, J. Hiao, Y. Liu, Z. L. Wu, J. Mol. Catal. B: Enzym., 2010, 67, 236.

    Article  CAS  Google Scholar 

  58. Y. Genzel, A. Archelas, J. H. Lutje Spelberg, D. B. Janssen, R. Furstoss, Tetrahedron, 2001, 57, 2775.

    Article  CAS  Google Scholar 

  59. Y. Genzel, A. Archelas, Q. B. Broxterman, B. Schulze, R. Furstoss, Tetrahedron Asymmetry, 2000, 11, 3041.

    Article  CAS  Google Scholar 

  60. Y. Genzel, A. Archelas, Q. B. Broxterman, B. Schulze, R. Furstoss, J. Org. Chem., 2001, 66, 538.

    Article  CAS  PubMed  Google Scholar 

  61. R. P. Hanzlik, M. Edelman, W. J. Michaely, G. Scott, J. Am. Chem. Soc., 1976, 98, 1952.

    Article  CAS  PubMed  Google Scholar 

  62. A. T. Nielsen, E. N. Platt, J. Heterocycl. Chem., 1969, 6, 891.

    Article  CAS  Google Scholar 

  63. C. R. Schmid, J. D. Bryant, M. Dowlatzedah, J. L. Philips, E. D. Prather, R. D. Schantz, N. L. Sear, C. S. Vianco, J. Org. Chem., 1991, 56, 4056.

    Article  CAS  Google Scholar 

  64. G. Chelucci, M. A. Cabras, A. Saba, Tetrahedron Asymmetry, 1994, 5, 1973.

    Article  CAS  Google Scholar 

  65. Yu. B. Zelechonok, S. S. Zlotskii, V. V. Zorin, D. L. Rakhmankulov, Chem. Heterocycl. Compd., 1990, 26, 487.

    Article  Google Scholar 

  66. V. V. Zorin, Yu. B. Zelechonok, S. S. Zlotskii, D. L. Rakhmankulov, J. Org. Chem. USSR, 1985, 21, 193.

    CAS  Google Scholar 

  67. T. S. Hamilton, R. Adams, J. Am. Chem. Soc., 1928, 50, 2260.

    Article  CAS  Google Scholar 

  68. K. V. Vatsuro, G. L. Mishchenko, Imennye reaktsii v organicheskoi khimii [Name Reactions in Organic Chemistry], Khimiya, Moscow, 1976, 528 pp. (in Russian).

    Google Scholar 

  69. A. Ladenburg, Ber. Dtsch. Chem. Ges., 1886, 19, 2578.

    Article  Google Scholar 

  70. R. S. P. Hsi, R. C. Thomas, J. Labelled Compd., 1973, 9, 425.

    Article  CAS  Google Scholar 

  71. C. Bhat, S. G. Tilve, Tetrahedron, 2013, 69, 10876.

    Article  CAS  Google Scholar 

  72. S. P. Chavan, L. B. Khairner, P. N. Chavan, D. B. Kalbroh, Tetrahedron Asymmetry, 2014, 25, 1246.

    Article  CAS  Google Scholar 

  73. P. Etayo, R. Badorrey, M. D. Díaz-De-Villegas, J. A. Gálvez, P. López-Ram-De-Víu, Synlett, 2010, 12, 1775.

    Google Scholar 

  74. C. Guérin, V. Bellosta, G. Guillamot, J. Cossy, Eur. J. Org. Chem., 2012, 15, 2990.

    Article  CAS  Google Scholar 

  75. C. Fernandez-Garcia, M. A. McKervey, Tetrahedron Asymmetry, 1995, 6, 2905.

    Article  CAS  Google Scholar 

  76. M. Breuning, M. Steiner, Tetrahedron Asymmetry, 2008, 19, 1978.

    Article  CAS  Google Scholar 

  77. M. Breuning, M. Steiner, Synthesis, 2006, 8, 1386.

    Article  CAS  Google Scholar 

  78. N. Hashimoto, T. Funatomi, T. Misakib, Y. Tanabeb, Tetrahedron, 2006, 62, 2214.

    Article  CAS  Google Scholar 

  79. M. Sax, B. Wünsch, Curr. Top. Med. Chem., 2006, 6, 723.

    Article  CAS  PubMed  Google Scholar 

  80. L. Temme, D. Schepmann, J. A. Schreiber, B. Frehland, B. Wünsch, ChemMedChem, 2018, 13, 446.

    Article  CAS  PubMed  Google Scholar 

  81. F. F. Blicke, F. E. Anderson, J. Am. Chem. Soc., 1952, 74, 1733.

    Article  CAS  Google Scholar 

  82. US Pat. 3256289; https://worldwide.espacenet.com.

  83. M. D. Mashkovski, N. I. Andreeva, A. N. Polezhaeva, Farmakologiya antidepressantov [Pharmacology of Antidepressants], Meditsina, Moscow, 1983, 121 pp. (in Russian).

    Google Scholar 

  84. M. Aepkers, B. Wünsch, Arch. Pharm. Pharm. Med. Chem., 2004, 337, 67.

    Article  CAS  Google Scholar 

  85. M. Aepkers, B. Wünsch, Bioorg. Med. Chem., 2005, 13, 683.

    Article  CAS  Google Scholar 

  86. US Pat. 3629287; https://worldwide.espacenet.com.

  87. M. Sax, K. Ebert, D. Schepmann, B. Wibbeling, B. Wünsch, Bioorg. Med. Chem., 2006, 14, 5955.

    Article  CAS  PubMed  Google Scholar 

  88. M. Sax, B. Wünsch, Aust. J. Chem., 2013, 66, 93.

    Article  CAS  Google Scholar 

  89. M. Sax, R. Fröhlich, D. Schepmann, B. Wünsch, Eur. J. Org. Chem., 2008, 1, 6015.

    Article  CAS  Google Scholar 

  90. A. Banerjee, R. Fröhlich, D. Schepmann, B. Wünsch, MedChemComm, 2010, 1, 87.

    Article  CAS  Google Scholar 

  91. A. Banerjee, D. Schepmann, J. Köhler, E.-U. Würthwein, B. Wünsch, Bioorg. Med. Chem., 2010, 18, 7855.

    Article  CAS  PubMed  Google Scholar 

  92. A. Banerjee, D. Schepmann, B. Wünsch, Bioorg. Med. Chem., 2010, 18, 4095.

    Article  CAS  PubMed  Google Scholar 

  93. T. Utech, J. Köhler, B. Wünsch, Eur. J. Med. Chem., 2011, 46, 2157.

    Article  CAS  PubMed  Google Scholar 

  94. J. Köhler, K. Bergander, J. Fabian, D. Schepmann, B. Wünsch, J. Med. Chem., 2012, 55, 8953.

    Article  PubMed  CAS  Google Scholar 

  95. A. Bonifazi, F. Del Bello, V. Mammoli, A. Piergentili, R. Petrelli, C. Cimarelli, M. Pellei, D. Schepmann, B. Wünsch, E. Barocelli, S. Bertoni, L. Flammini, C. Amantini, M. Nabissi, G. Santoni, G. Vistoli, W. Quaglia, J. Med. Chem., 2015, 58, 8601.

    Article  CAS  PubMed  Google Scholar 

  96. D. E. Koshland, Proc. Natl. Acad. Sci. USA, 1958, 44, 98.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  97. E. Fischer, Ber. Dtsch. Chem. Ges., 1894, 27, 2985.

    Article  CAS  Google Scholar 

  98. S. Asare-Nkansah, B. Wünsch, Molecules, 2016, 21, 1503.

    Article  PubMed Central  CAS  Google Scholar 

  99. S. Asare-Nkansah, D. Schepmann, B. Wünsch, Bioorg. Med. Chem., 2017, 25, 2472.

    Article  CAS  PubMed  Google Scholar 

  100. W. G. North, G. Gao, V. A. Memoli, R. H. Pang, L. Lynch, Breast Cancer Res. Treat., 2010, 122, 307.

    Article  CAS  PubMed  Google Scholar 

  101. M. B. Morelli, C. Amantini, G. Santoni, M. Pellei, C. Santini, C. Cimarelli, E. Marcantoni, M. Petrini, F. Del Bello, G. Giorgioni, A. Piergentili, W. Quaglia, New J. Chem., 2018, 42, 11878.

    Article  CAS  Google Scholar 

  102. M. B. Morelli, C. Amantini, M. Nabissi, G. Santoni, B. Wünsch, D. Schepmann, C. Cimarelli, M. Pellei, C. Santini, S. Fontana, V. Mammoli, W. Quaglia, A. Bonifazi, M. Giannella, G. Giorgioni, A. Piergentili, F. Del Bello, ACS Med. Chem. Lett., 2019, 10, 511.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  103. S. Dei, C. Bellucci, M. Buccioni, M. Ferraroni, L. Guandalini, D. Manetti, E. Martini, G. Marucci, R. Matucci, M. Nesi, M. N. Romanelli, S. Scapecchi, E. Teodori, J. Med. Chem., 2007, 50, 1409.

    Article  CAS  PubMed  Google Scholar 

  104. S. Dei, C. Bellucci, M. Buccioni, M. Ferraroni, F. Gualtieri, L. Guandalini, D. Manetti, R. Matucci, M. N. Romanelli, S. Scapecchia, E. Teodoria, Bioorg. Med. Chem., 2003, 11, 3153.

    Article  CAS  PubMed  Google Scholar 

  105. S. Scapecchi, R. Matucci, C. Bellucci, M. Buccioni, S. Dei, L. Guandalini, C. Martelli, D. Manetti, E. Martini, G. Marucci, M. Nesi, M. N. Romanelli, E. Teodori, F. Gualtieri, J. Med. Chem., 2006, 49, 1925.

    Article  CAS  PubMed  Google Scholar 

  106. S. Dei, C. Bellucci, M. Buccioni, M. Ferraroni, L. Guandalini, D. Maetti, G. Marucci, R. Matucci, M. Nesi, M. N. Romanelli, S. Scapecchi, E. Teodori, Bioorg. Med. Chem., 2008, 16, 5490.

    Article  CAS  PubMed  Google Scholar 

  107. A. Bonifazi, A. Piergentili, F. Del Bello, Y. Farande, M. Giannella, M. Pigini, C. Amantini, M. Nabissi, V. Farfariello, Giorgio Santoni, E. Poggesi, A. Leonardi, S. Menegon, W. Quaglia, J. Med. Chem., 2013, 56, 584.

    Article  CAS  PubMed  Google Scholar 

  108. F. Del Bello, A. Bonifazi, G. Giorgioni, W. Quaglia, C. Amantini, M. B. Morelli, G. Santoni, F. O. Battiti, G. Vistoli, A. Cilia, A. Piergentili, Eur. J. Org. Chem., 2019, 1, 461.

    Google Scholar 

  109. S. Franchini, C. Sorbi, P. Linciano, L. Brasili, A. Tait, Pharmazie, 2019, 74, 131.

    CAS  PubMed  Google Scholar 

  110. S. B. Lorette, W. L. Howard, J. Org. Chem., 1960, 25, 521.

    Article  CAS  Google Scholar 

  111. A. Thurkauf, A. E. Jacobson, K. C. Rice, Synthesis, 1988, 233.

  112. W. Voss, Ann. Chem., 1931, 485, 283.

    Article  CAS  Google Scholar 

  113. C. Weygand, G. Hilgetag, Organisch-chemische Experimentierkunst, J. A. Barth, Leipzig, 1970.

    Google Scholar 

  114. N. Hamada, K. Kazahaya, H. Shimizu, T. Sato, Synlett, 2004, 6, 1074.

    Google Scholar 

  115. V. I. Petrov, L. B. Piotrovskii, I. A. Grigor’ev, Vozbuzhdayushchie aminokisloty [Excitatory Amino Acids], Volgogr. med. akademiya, Volgograd, 1997, 166 pp. (in Russian).

    Google Scholar 

  116. P. V. Sergeev, N. L. Shimanovskii, V. I. Petrov, Retseptory fiziologicheski aktivnykh veshchestv [Receptors of Physiologically Active Substances], Sem’ vetrov, Volgograd, 1999, 640 pp. (in Russian).

    Google Scholar 

  117. S. Budavari, M. O’Neill, A. Smith, P. Heckelman, J. Kinnear, The Merck Index, 12th ed., Chapman and Hall, New York, 1997.

    Google Scholar 

  118. R. B. Moffett, R. E. Strube, L. Skaletzky, J. Med. Chem., 1971, 14, 1088.

    Article  CAS  PubMed  Google Scholar 

  119. A. H. Tang, A. A. Cangelosi, R. A. Code, S. R. Franklin, Pharmacol. Biochem. Behav., 1984, 20, 209.

    Article  CAS  PubMed  Google Scholar 

  120. J. C. Blake, S. N. Davies, J. Church, D. Martin, D. Lodge, Pharmacol. Biochem. Behav., 1986, 24, 23.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Volgograd State Technical University, 28 prosp. Lenina, 400005, Volgograd, Russian Federation

    I. A. Novakov, D. S. Sheikin, M. B. Navrotskii, A. S. Mkrtchyan & L. L. Brunilina

  2. Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    K. V. Balakin

Authors
  1. I. A. Novakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. S. Sheikin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. B. Navrotskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. S. Mkrtchyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. L. Brunilina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. K. V. Balakin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. B. Navrotskii.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 19-13-00123).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1625–1671, September, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Novakov, I.A., Sheikin, D.S., Navrotskii, M.B. et al. Dexoxadrol and its bioisosteres: structure, synthesis, and pharmacological activity. Russ Chem Bull 69, 1625–1671 (2020). https://doi.org/10.1007/s11172-020-2946-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-2946-9

Key words

Search

Navigation