Examples



mdbootstrap.com



 
Статья
2020

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


I. A. NovakovI. A. Novakov, D. S. SheikinD. S. Sheikin, M. B. NavrotskiiM. B. Navrotskii, A. S. MkrtchyanA. S. Mkrtchyan, L. L. BrunilinaL. L. Brunilina, K. V. BalakinK. V. Balakin
Российский химический вестник
https://doi.org/10.1007/s11172-020-2946-9
Abstract / Full Text

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.

Author information
  • Volgograd State Technical University, 28 prosp. Lenina, 400005, Volgograd, Russian FederationI. A. Novakov, D. S. Sheikin, M. B. Navrotskii, A. S. Mkrtchyan & L. L. Brunilina
  • Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian FederationK. V. Balakin
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.
  2. D. Lodge, M. S. Mercier, Br. J. Pharmacol., 2015, 172, 4254.
  3. A. Nowacka, M. Borczyk, Eur. J. Pharmacol., 2019, 860, 172547.
  4. A. Slomski, J. Am. Med. Ass., 2019, 322, 2375.
  5. C. Andrade, J. Clin. Psychiatry, 2017, 78, e674.
  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.
  7. T. H. Pham, A. M. Gardier, Pharmacol. Ther., 2019, 199, 58.
  8. B. Pochwat, A. Palucha-Poniewiera, B. Szewczyk, A. Pilc, G. Nowak, Expert Opin. Investig. Drugs, 2014, 23, 1457.
  9. B. Pochwat, A. Palucha-Poniewiera, B. Szewczyk, Expert Rev. Neurother., 2019, 67, 1.
  10. J. Kornhuber, C. G. Parsons, S. Hartmann, W. Retz, S. Kamolz, J. Thome, P. Riederer, J. Neural Transm., 1995, 102, 237.
  11. BE Pat. 628167; https://worldwide.espacenet.com.
  12. J. Hidalgo, J. Gallin, A. Williams, C. R. Thompson, Pharmacologist, 1961, 3, 69.
  13. T. P. Pruss, J. Hidalgo, C. R. Thompson, Proc. West. Pharm. Soc., 1963, 6, 40.
  14. J. Hidalgo, C. R. Thompson, Proc. Soc. Exp. Biol. Med., 1963, 114, 92.
  15. J. Hidalgo, C. R. Thompson, Arch. Int. Pharmacodyn., 1965, 105, 153.
  16. R. Tar & Chem. Corp., Ind. Eng. Chem. Res., 1960, 52, 55A.
  17. US Pat. 2421714; https://worldwide.espacenet.com.
  18. F. F. Blicke, E. L. Schumann, J. Am. Chem. Soc., 1952, 74, 2613.
  19. W. R. Hardie, J. Hidalgo, I. F. Halverstandt, R. E. Allen, J. Med. Chem., 1966, 9, 127.
  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.
  23. A. Thurkauf, M. V. Mattson, P. N. Huguenin, K. C. Rice, A. E. Jacobson, FEBS Lett., 1988, 238, 369.
  24. CA Pat. 900487; https://worldwide.espacenet.com.
  25. C. Bhat, Chemistry Open, 2015, 4, 192.
  26. C. Bhat, S. T. Budge, S. G. Tilve, Synthesis, 2014, 46, 2551.
  27. G. Raju, K. Anitha, P. R. Krishna, Synlett, 2015, 26, 937.
  28. F. M. Cordero, C. Vurchio, A. Brandi, J. Org. Chem., 2016, 81, 1661.
  29. F. M. Cordero, D. Giomi, A. Brandi, Curr. Top. Med. Chem., 2014, 14, 1294.
  30. I. Pastuszak, R. J. Molyneux, L. F. James, A. D. Elbein, Biochemistry, 1990, 29, 1886.
  31. B. Macchi, A. Minutolo, S. Grelli, F. Cardona, F. M. Cordero, A. Mastino, A. Brandi, Glycobiology, 2010, 20, 500.
  32. A. Minutolo, S. Grelli, F. Marino-Merlo, F. M. Cordero, A. Brandi, B. Macchi, A. Mastino, Cell Death Dis., 2012, 3, e358.
  33. J. Mondal, A. Panigrahi, A. R. Khuda-Bukhsh, Pharmacogn. Mag., 2014, 10, S524.
  34. S. F. Kramer, G. L. Flynn, J. Pharm. Sci., 1972, 61, 1897.
  35. L. W. Brown, A. A. Forist, J. Pharm. Sci., 1973, 62, 1365.
  36. S. Lee, B. T. Green, K. D. Welch, J. A. Plister, K. E. Panter, Chem. Res. Toxicol., 2008, 21, 2061.
  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).
  40. H. C. Haas, H. S. Kolesninski, N. W. Shuler, Polym. Lett., 1965, 3, 879.
  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.
  42. D. L. Klayman, A. l. Lin, J. M. Hoch, J. P. Scovill, C. Lambros, A. S. Dobek, J. Pharm. Sci., 1984, 73, 1763.
  43. W. Sauermilch, Chem. Ber., 1957, 90, 833.
  44. W. Winker, Chem. Ber., 1948, 81, 256.
  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.
  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.
  48. G. He, S. Zhang, W. A. Nack, R. Pearson, J. Rabb-Lynch, G. Chen, Org. Lett., 2014, 16, 6488.
  49. A. Mikleušević, I. Primožič, T. Hrenar, B. Salopek-Sondi, L. Tang, M. M. Elenkov, Tetrahedron Asymmetry, 2016, 27, 930.
  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.
  51. R. Menasse, G. Klein, H. Erlenmeyer, Helv. Chim. Acta, 1955, 38, 1289.
  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.
  53. S. T. Liu, K. V. Reddy, R. Y. Lai, Tetrahedron, 2007, 63, 1821.
  54. K. Kloc, E. Kubicz, J. Mlkochowski, Heterocycles, 1984, 22, 2517.
  55. H. Toda, R. Imae, N. Itoh, Tetrahedron Asymmetry, 2012, 23, 1542.
  56. S. Bernasconi, F. Orsini, G. Sello, A. Colmegna, E. Galli, G. Bestetti, Tetrahedron Lett., 2000, 41, 9157.
  57. H. Lin, J. Hiao, Y. Liu, Z. L. Wu, J. Mol. Catal. B: Enzym., 2010, 67, 236.
  58. Y. Genzel, A. Archelas, J. H. Lutje Spelberg, D. B. Janssen, R. Furstoss, Tetrahedron, 2001, 57, 2775.
  59. Y. Genzel, A. Archelas, Q. B. Broxterman, B. Schulze, R. Furstoss, Tetrahedron Asymmetry, 2000, 11, 3041.
  60. Y. Genzel, A. Archelas, Q. B. Broxterman, B. Schulze, R. Furstoss, J. Org. Chem., 2001, 66, 538.
  61. R. P. Hanzlik, M. Edelman, W. J. Michaely, G. Scott, J. Am. Chem. Soc., 1976, 98, 1952.
  62. A. T. Nielsen, E. N. Platt, J. Heterocycl. Chem., 1969, 6, 891.
  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.
  64. G. Chelucci, M. A. Cabras, A. Saba, Tetrahedron Asymmetry, 1994, 5, 1973.
  65. Yu. B. Zelechonok, S. S. Zlotskii, V. V. Zorin, D. L. Rakhmankulov, Chem. Heterocycl. Compd., 1990, 26, 487.
  66. V. V. Zorin, Yu. B. Zelechonok, S. S. Zlotskii, D. L. Rakhmankulov, J. Org. Chem. USSR, 1985, 21, 193.
  67. T. S. Hamilton, R. Adams, J. Am. Chem. Soc., 1928, 50, 2260.
  68. K. V. Vatsuro, G. L. Mishchenko, Imennye reaktsii v organicheskoi khimii [Name Reactions in Organic Chemistry], Khimiya, Moscow, 1976, 528 pp. (in Russian).
  69. A. Ladenburg, Ber. Dtsch. Chem. Ges., 1886, 19, 2578.
  70. R. S. P. Hsi, R. C. Thomas, J. Labelled Compd., 1973, 9, 425.
  71. C. Bhat, S. G. Tilve, Tetrahedron, 2013, 69, 10876.
  72. S. P. Chavan, L. B. Khairner, P. N. Chavan, D. B. Kalbroh, Tetrahedron Asymmetry, 2014, 25, 1246.
  73. P. Etayo, R. Badorrey, M. D. Díaz-De-Villegas, J. A. Gálvez, P. López-Ram-De-Víu, Synlett, 2010, 12, 1775.
  74. C. Guérin, V. Bellosta, G. Guillamot, J. Cossy, Eur. J. Org. Chem., 2012, 15, 2990.
  75. C. Fernandez-Garcia, M. A. McKervey, Tetrahedron Asymmetry, 1995, 6, 2905.
  76. M. Breuning, M. Steiner, Tetrahedron Asymmetry, 2008, 19, 1978.
  77. M. Breuning, M. Steiner, Synthesis, 2006, 8, 1386.
  78. N. Hashimoto, T. Funatomi, T. Misakib, Y. Tanabeb, Tetrahedron, 2006, 62, 2214.
  79. M. Sax, B. Wünsch, Curr. Top. Med. Chem., 2006, 6, 723.
  80. L. Temme, D. Schepmann, J. A. Schreiber, B. Frehland, B. Wünsch, ChemMedChem, 2018, 13, 446.
  81. F. F. Blicke, F. E. Anderson, J. Am. Chem. Soc., 1952, 74, 1733.
  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).
  84. M. Aepkers, B. Wünsch, Arch. Pharm. Pharm. Med. Chem., 2004, 337, 67.
  85. M. Aepkers, B. Wünsch, Bioorg. Med. Chem., 2005, 13, 683.
  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.
  88. M. Sax, B. Wünsch, Aust. J. Chem., 2013, 66, 93.
  89. M. Sax, R. Fröhlich, D. Schepmann, B. Wünsch, Eur. J. Org. Chem., 2008, 1, 6015.
  90. A. Banerjee, R. Fröhlich, D. Schepmann, B. Wünsch, MedChemComm, 2010, 1, 87.
  91. A. Banerjee, D. Schepmann, J. Köhler, E.-U. Würthwein, B. Wünsch, Bioorg. Med. Chem., 2010, 18, 7855.
  92. A. Banerjee, D. Schepmann, B. Wünsch, Bioorg. Med. Chem., 2010, 18, 4095.
  93. T. Utech, J. Köhler, B. Wünsch, Eur. J. Med. Chem., 2011, 46, 2157.
  94. J. Köhler, K. Bergander, J. Fabian, D. Schepmann, B. Wünsch, J. Med. Chem., 2012, 55, 8953.
  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.
  96. D. E. Koshland, Proc. Natl. Acad. Sci. USA, 1958, 44, 98.
  97. E. Fischer, Ber. Dtsch. Chem. Ges., 1894, 27, 2985.
  98. S. Asare-Nkansah, B. Wünsch, Molecules, 2016, 21, 1503.
  99. S. Asare-Nkansah, D. Schepmann, B. Wünsch, Bioorg. Med. Chem., 2017, 25, 2472.
  100. W. G. North, G. Gao, V. A. Memoli, R. H. Pang, L. Lynch, Breast Cancer Res. Treat., 2010, 122, 307.
  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.
  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.
  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.
  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.
  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.
  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.
  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.
  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.
  109. S. Franchini, C. Sorbi, P. Linciano, L. Brasili, A. Tait, Pharmazie, 2019, 74, 131.
  110. S. B. Lorette, W. L. Howard, J. Org. Chem., 1960, 25, 521.
  111. A. Thurkauf, A. E. Jacobson, K. C. Rice, Synthesis, 1988, 233.
  112. W. Voss, Ann. Chem., 1931, 485, 283.
  113. C. Weygand, G. Hilgetag, Organisch-chemische Experimentierkunst, J. A. Barth, Leipzig, 1970.
  114. N. Hamada, K. Kazahaya, H. Shimizu, T. Sato, Synlett, 2004, 6, 1074.
  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).
  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).
  117. S. Budavari, M. O’Neill, A. Smith, P. Heckelman, J. Kinnear, The Merck Index, 12th ed., Chapman and Hall, New York, 1997.
  118. R. B. Moffett, R. E. Strube, L. Skaletzky, J. Med. Chem., 1971, 14, 1088.
  119. A. H. Tang, A. A. Cangelosi, R. A. Code, S. R. Franklin, Pharmacol. Biochem. Behav., 1984, 20, 209.
  120. J. C. Blake, S. N. Davies, J. Church, D. Martin, D. Lodge, Pharmacol. Biochem. Behav., 1986, 24, 23.