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2-Thioxo-tetrahydro-4H-imidazol-4-ones, 2-alkylthio-3,5-dihydro-4H-imidazol-4-ones and their coordination compounds with transition metal ions

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Abstract

Data published in the past decade on the methods of synthesis of 2-thiohydantoins and 2-alkylthio-3,5-dihydro-4H-imidazol-4-ones are reviewed. Methods used to introduce various functional groups into positions 2 and 5 of thiohydantoin or 3,5-dihydro-4H-imidazol-4-ones by using the condensation and nucleophilic substitution reactions are considered. The reactions of complex formation with the participation of thiohydantoins and 3,5-dihydro-4H-imidazol-4-ones are analyzed, and the data on synthesis methods, structural types, and catalytic activity of their complexes with transition metals are presented.

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References

  1. Ware, E., Chem. Rev., 1950, vol. 46, no. 3, p. 403.

    Article  CAS  Google Scholar 

  2. Mukarjee, A.K. and Ashare, R., Chem. Rev., 1991, vol. 91, no. 1, p. 1.

    Article  Google Scholar 

  3. Scheinder, S.E., Bishop, P.A., Salazar, M.A., Bishop, O.A., and Anslyn, E.V., Tetrahedron, 1998, vol. 54, no. 50, p. 15063.

    Article  Google Scholar 

  4. Khodair, A.I. and Bertrand, P., Tetrahedron, 1998, vol. 54, no. 19, p. 4859.

    Article  CAS  Google Scholar 

  5. Chen, J., Pattarawarapan, M., Zhang, A., and Burgess, K., J. Comb. Chem., 2000, vol. 2, no. 2, p. 276.

    Article  CAS  Google Scholar 

  6. Gyemánt, G., Kandra, L., Nagy, V., and Somsak, L., Biochem. Biophys. Res. Commun., 2003, vol. 312, no. 2, p. 334.

    Article  Google Scholar 

  7. Cheng, C.-K., Wu, J., Liu, Y., Lee, T.-S., Kang, S.-J., Sheu, M.-T., and Lee, W.-S., Vascular Pharmacol., 2008, vol. 48, no. 3, p. 138.

    Article  CAS  Google Scholar 

  8. Edman, P., Acta Chem. Scand., 1950, vol. 4, no. 4, p. 283.

    Article  CAS  Google Scholar 

  9. Horton, D.A., Bourne, G.T., Coughlan, J., Kaiser, S.M., Jacobs, C.M., Jones, A., Rhmann, A., Turner, J.Y., and Smythe, M.L., Org. Biomol. Chem., 2008, vol. 6, no. 10, p. 1386.

    Article  CAS  Google Scholar 

  10. Jullian, M., Hernandez, A., Maurras, A., Puget, K., Amblard, M., Martinez, J., and Subra, G., Tetrahedron Lett., 2009, vol. 50, no. 3, p. 260.

    Article  CAS  Google Scholar 

  11. Davies, R., Hedebrant, U., Athanassiadis, I., Rydberg, P., and Tornqvist, M., Food Chem. Toxicol., 2009, vol. 47, no. 8, p. 1950.

    Article  CAS  Google Scholar 

  12. Majouga, A.G., Beloglazkina, E.K., Vatsadze, S.Z., Moiseeva, A.A., Moiseev, F.S., Butin, K.P., and Zyk, N.V., Mendeleev Commun., 2005, vol. 15, no. 2, p. 48.

    Article  Google Scholar 

  13. Beloglazkina, E.K., Majouga, A.G., Moiseeva, A.A., Zyk, N.V., and Zefirov, N.S., Mendeleev Commun., 2009, vol. 19, no. 1, p. 69.

    Article  CAS  Google Scholar 

  14. Reyes, S. and Burgess, K., J. Org. Chem., 2006, vol. 71, no. 6, p. 2507.

    Article  CAS  Google Scholar 

  15. Cherouvrier, J.-R., Carreaux, F., and Bazureau, J.P., Tetrahedron Lett., 2002, vol. 43, no. 48, p. 8745.

    Article  CAS  Google Scholar 

  16. Somsak, L., Kovacs, L., Toth, M., Osz, E., Szilagyi, L., Gyorgydeak, Z., Dinya, Z., Docsa, T., Toth, B., and Gergely, P., J. Med. Chem., 2001, vol. 44, no. 17, p. 2843.

    Article  CAS  Google Scholar 

  17. Chu, Y., Lynch, V., and Iverson, B.L., Tetrahedron, 2006, vol. 62, no. 23, p. 5536.

    Article  CAS  Google Scholar 

  18. Blanco-Ania, D., Hermkens, P.D.D., Sliedregt, L.A.J.M., Scheeren, H.W., and Rutjes, F.P.J.T., J. Comb. Chem., 2009, vol. 11, no. 4, p. 527.

    Article  CAS  Google Scholar 

  19. Fuentes, J., Salameh, B.A.B.M., and Pradera, M.A., Fernndez De Crdoba F.J., Gasch C, Tetrahedron, 2006, vol. 62, no. 37, p. 97.

    Article  CAS  Google Scholar 

  20. Cherouvrier, J.-R., Carreaux, F., and Bazureau, J.P., Tetrahedron Lett., 2002, vol. 43, no. 19, p. 3581.

    Article  CAS  Google Scholar 

  21. Renault, S., Bertrand, S., Carreaux, F., and Bazureau, J.P., J. Comb. Chem., 2007, vol. 9, no. 6, p. 935.

    Article  CAS  Google Scholar 

  22. Gregg, B.T., Golden, K.C., Quinn, J.F., Tymoshenko, D.O., Earley, W.G., Maynard, D.A., Razzano, D.A., Rennells, W.M., and Butcher, J., J. Comb. Chem., 2007, vol. 9, no. 6, p. 1036.

    Article  CAS  Google Scholar 

  23. Pal, M., Tetrahedron, 2009, vol. 65, no. 2, p. 433.

    Article  CAS  Google Scholar 

  24. Ganesan, A., Pure Appl. Chem., 2001, vol. 73, no. 7, p. 1033.

    Article  CAS  Google Scholar 

  25. Jansen, M., Potschka, H., Brandt, C., Loscher, W., and Dannhardt, G., J. Med. Chem., 2003, vol. 46, no. 1, p. 64.

    Article  CAS  Google Scholar 

  26. Elokdah, H., Sulkowski, T.S., Abou-Gharbia, M., Butera, J.A., Chai, S.-Y., McFarlane, G.R., McKean, M.-L., Babiak, J.L., Adelman, S.J., and Quinet, E.M., J. Med. Chem., 2004, vol. 47, no. 2, p. 681.

    Article  CAS  Google Scholar 

  27. Zhang, W. and Lu, Y., Org. Lett., 2003, vol. 5, no. 14, p. 2555.

    Article  CAS  Google Scholar 

  28. Zhang, W., Chem. Rev., 2004, vol. 104, no. 5, p. 2531.

    Article  CAS  Google Scholar 

  29. Voss, M.E., Carter, P.H., Tebben, A.J., Scherle, P.A., Brown, G.D., Thompson, L.A., Xu, M., Lo, Y.C., Yang, G., Liu, R.-Q., Strzemienski, P., Everlof, J.G., Trzaskos, J.M., and Decicco, C.P., Bioorg. Med. Chem. Lett., 2003, vol. 13, no. 3, p. 533.

    Article  CAS  Google Scholar 

  30. Cao, S., Zhu, L., Zhao, C., Tang, X., Sun, H., Feng, X., and Qian, X., Monatsh. Chem., 2008, vol. 139, no. 8, p. 923.

    Article  CAS  Google Scholar 

  31. Incesu, Z., Benkli, K., Akalin, G., and Kaplancikli, Z.A., Cell Biol. Int., 2004, vol. 2, no. 2, p. 267.

    Article  Google Scholar 

  32. Zhang, X., Zheng, L., Gao, J., Liu, Q., Sun, G., Qin, L., and Zhang, S., Chem. Res. Chin. Univ., 2009, vol. 25, no. 5, p. 648.

    Google Scholar 

  33. Ma, C.-M., Li, J.-P., and Zheng, P.-Z., Heterocycles, 2005, vol. 65, no. 2, p. 359.

    Article  CAS  Google Scholar 

  34. Li, J.-P., Ma, C.-M., and Qu, G.-R., Synth. Commun., 2005, vol. 35, no. 9, p. 1203.

    Article  CAS  Google Scholar 

  35. Lin, M.-J. and Sun, C.-M., Tetrahedron Lett., 2003, vol. 44, no. 48, p. 8739.

    Article  CAS  Google Scholar 

  36. Chang, W.-J., Kulkarni, M.V., and Sun, C.-M., J. Comb. Chem., 2006, vol. 8, no. 2, p. 141.

    Article  CAS  Google Scholar 

  37. Blanco-Ania, D., Hermkens, P.D.D., Sliedregt, L.A.J.M., Scheeren, H.W., and Rutjes, F.P.J.T., J. Comb. Chem., 2009, vol. 11, no. 3, p. 547.

    Article  CAS  Google Scholar 

  38. Van Dort, M.E. and Jung, Y.-W., Bioorg. Med. Chem. Lett., 2004, vol. 14, no. 10, p. 5285.

    Article  Google Scholar 

  39. Fresneda, P.M., Castaeda, M., Sanz, M.A., and Molina, P., Tetrahedron Lett., 2004, vol. 45, no. 8, p. 1655.

    Article  CAS  Google Scholar 

  40. Fresneda, P.M., Castaeda, M., Sanz, M.A., Bautista, D., and Molina, P., Tetrahedron, 2007, vol. 63, no. 8, p. 1849.

    Article  CAS  Google Scholar 

  41. Aguilar-Moncayo, M., Mellet, C.O., Fernandez, J.M.G., and Garca-Moreno, M.I., J. Org. Chem., 2009, vol. 74, no. 9, p. 3595.

    Article  CAS  Google Scholar 

  42. Ryczek, J., J. Heterocycl. Chem., 2003, vol. 40, no. 4, p. 665.

    Article  CAS  Google Scholar 

  43. Gasch, C., Illangua, J.M., Merino-Montiel, P., and Fuentes, J., Tetrahedron, 2009, vol. 65, no. 21, p. 4149.

    Article  CAS  Google Scholar 

  44. Faghihi, K., Zamani, K., Mirsamie, A., and Sangi, M.R., Eur. Polymer J., 2003, vol. 39, no. 2, p. 247.

    Article  CAS  Google Scholar 

  45. Kashem Liton, A. and Rabuil Islam, M., Bangladesh J. Pharmacol., 2006, vol. 1, no. 1, p. 10.

    Google Scholar 

  46. Muccioli, G.G., Poupaert, J.H., Wouters, J., Norberg, B., Poppitz, W., Scribad, G.K.E., and Lambert, D.M., Tetrahedron, 2003, vol. 59, no. 8, p. 1301.

    Article  CAS  Google Scholar 

  47. Schmeyers, J. and Kaupp, G., Tetrahedron, 2002, vol. 58, no. 36, p. 7241.

    Article  CAS  Google Scholar 

  48. Muccioli, G.G., Martin, D., Scriba, G.K.E., Poppitz, W., Poupaert, J.H., Wouters, J., and Lambert, D.M., J. Med. Chem., 2005, vol. 48, no. 7, p. 2509.

    Article  CAS  Google Scholar 

  49. Muccioli, G.G., Wouters, J., Poupaert, J.H., Norberg, B., Poppitz, W., Scriba, G.K.E., and Lambert, D.M., Org. Lett., 2003, vol. 5, no. 20, p. 3599.

    Article  CAS  Google Scholar 

  50. Thanusu, J., Kanagarajan, V., and Gopalakrishnan, M., Bioorg. Med. Chem. Lett., 2010, vol. 20, no. 2, p. 713.

    Article  CAS  Google Scholar 

  51. Patel, R.B., Desai, K.R., and Chikhalia, K.H., Indian J. Chem., B, 2006, vol. 45, no. 10, p. 1716.

    Google Scholar 

  52. Balya, A.G., Chernega, A.N., But, S.A., Vasilenko, A.N., Brovarets, V.S., and Drach, B.S., Russ. J. Gen. Chem., vol. 78, no. 7, p. 1427.

  53. Wang, X.-J., Zhang, L., Xu, Y., Krishnamurthy, D., Varsolona, R., Nummy, L., Shen, S., Frutos, R.P., Byrne, D., Chung, J.C., Farina, V., and Senanayake, C.H., Tetrahedron Lett., 2005, vol. 46, no. 2, p. 273.

    Article  Google Scholar 

  54. Geffken, D. and Ploetz, A., Z. Naturforsch., B, 2006, vol. 61, no. 1, p. 83.

    CAS  Google Scholar 

  55. Nefzi, A., Giulianotti, M., Truong, L., Rattan, S., Ostresh, J.M., and Houghten, R.A., J. Comb. Chem., 2002, vol. 4, no. 2, p. 175.

    Article  CAS  Google Scholar 

  56. Nefzi, A., Ostresh, J.M., Yu, J., and Houghten, R.A., J. Org. Chem., 2004, vol. 69, no. 11, p. 3603.

    Article  CAS  Google Scholar 

  57. Toussaint, M., Mousset, D., Foulon, C., Jacquemard, U., Vaccher, C., and Melnyk, P., Eur. J. Med. Chem., 2010, vol. 45, no. 1, p. 256.

    Article  CAS  Google Scholar 

  58. Sundaram, G.S.M., Venkatesh, C., Ila, H., and Junjappa, H., Synlett, 2007, vol. 2, no. 2, p. 251.

    Google Scholar 

  59. Hupp, C.D. and Tepe, J.J., Org. Lett., 2008, vol. 10, no. 17, p. 3737.

    Article  CAS  Google Scholar 

  60. Singh, B., Sundaram, G.S.M., Misra, N.C., and Ila, H., Tetrahedron Lett., 2009, vol. 50, no. 3, p. 366.

    Article  CAS  Google Scholar 

  61. Porwal, S., Kumar, R., Maulik, P.R., and Chauhan, P.M.S., Tetrahedron Lett., 2006, vol. 47, no. 33, p. 5863.

    Article  CAS  Google Scholar 

  62. Majouga, A.G., Beloglazkina, E.K., Vatsadze, S.Z., Frolova, N.A., and Zyk, N.V., Izv. Akad. Nauk, Ser. Khim., 2004, no. 12, p. 2734.

  63. Beloglazkina, E.K., Majouga, A.G., Yudin, I.V., Frolova, N.A., Zyk, N.V., Dolzhikova, V.D., Moiseeva, A.A., Rakhimov, R.D., and Butin, K.P., Izv. Akad. Nauk, Ser. Khim., 2006, no. 6, p. 978.

  64. Vatsadze, S.Z., Majouga, A.G., Beloglazkina, E.K., Mironov, A.V., and Zyk, N.V., Mendeleev Commun., 2007, vol. 17, no. 2, p. 77.

    Article  CAS  Google Scholar 

  65. Yang, F.-L., Liu, Z.-J., Huang, X.-B., and Ding, M.-W., J. Heterocycl. Chem., 2004, vol. 41, no. 1, p. 77.

    Article  CAS  Google Scholar 

  66. Carboni, M., Gomis, J.-M., Loreau, O., and Taran, F., Synthesis, 2008, vol. 40, no. 3, p. 417.

    Google Scholar 

  67. Kiec-Kononowicz, K. and Szymanska, E., Il Farmaco, 2002, vol. 57, no. 11, p. 909.

    Article  CAS  Google Scholar 

  68. Kiec-Kononowicz, K., Karolak-Wojciechowska, J., Michalak, B., Pekala, E., Schumacher, B., and Muller, C.E., Eur. J. Med. Chem., 2004, vol. 39, no. 2, p. 205.

    Article  CAS  Google Scholar 

  69. Ates-Alagoz, Z., Altanlar, N., and Buyukbingol, E., J. Heterocycl. Chem., 2009, vol. 46, no. 6, p. 1375.

    Article  CAS  Google Scholar 

  70. Khodair, A.I., Carbohydr. Res., 2001, vol. 331, no. 4, p. 445.

    Article  CAS  Google Scholar 

  71. Kiec-Kononowicz, K., Muller, C.E., Pekala, E., Karolak-Wojciechowska, J., Handzlik, J., and Lazewska, D., J. Heterocycl. Chem., 2002, vol. 39, no. 2, p. 243.

    Article  CAS  Google Scholar 

  72. Aly, Y.L., J. Sulfur Chem., 2007, vol. 28, no. 3, p. 371.

    Article  CAS  Google Scholar 

  73. Ermoli, A., Bargiotti, A., Brasca, M.G., Ciavolella, A., Colombo, N., Fachin, G., Isacchi, A., Menichincheri, M., Molinari, A., Montagnoli, A., Pillan, A., Rainoldi, S., Sirtori, F.R., Sola, F., Thieffine, S., Tibolla, M., Valsasina, B., Volpi, D., Santocanale, C., and Vanotti, E., J. Med. Chem., 2009, vol. 52, no. 14, p. 4380.

    Article  CAS  Google Scholar 

  74. Davis, R.A., Baron, P.S., Neve, J.E., and Cullinane, C., Tetrahedron Lett., 2009, vol. 50, no. 8, p. 880.

    Article  CAS  Google Scholar 

  75. Aly, Y.L., Phosphorus, Sulfur Silicon Relat. Elem., 2005, vol. 180, no. 1, p. 1.

    Article  CAS  Google Scholar 

  76. Jakse, R., Bevk, D., Golobic, A., Svete, J., and Stanovnik, B., Z. Naturforsch., B, 2006, vol. 61, no. 4, p. 413.

    CAS  Google Scholar 

  77. Chowdhry, M.M., Mingos, D.M.P., White, A.J.P., and Williams, D.J., J. Chem. Soc., Perkin Trans., 2000, vol. 1, no. 20, p. 3495.

    Article  Google Scholar 

  78. Cherouvrier, J.-R., Boissel, J., Carreaux, F., and Bazureau, J.-P., Green Chem., 2001, vol. 3, no. 4, p. 165.

    Article  CAS  Google Scholar 

  79. Stanovnik, B. and Svete, J.J., Chem. Rev., 2004, vol. 104, no. 5, p. 2433.

    Article  CAS  Google Scholar 

  80. Portevin, B., Golsteyn, R.M., Pierre, A., and De Nanteuil, G., Tetrahedron Lett., 2003, vol. 44, no. 52, p. 9263.

    Article  CAS  Google Scholar 

  81. Szymanska, E., Kiec-Kononowicz, K., Biaecka, A., and Kasprowicz, A., Il Farmaco, 2002, vol. 57, no. 1, p. 39.

    Article  CAS  Google Scholar 

  82. Szymanska, E. and Kiec-Kononowicz, K., Il Farmaco, 2002, vol. 57, no. 5, p. 355.

    Article  CAS  Google Scholar 

  83. Kumar, R. and Chauhan, P.M.S., Tetrahedron Lett., 2008, vol. 49, no. 38, p. 5475.

    Article  CAS  Google Scholar 

  84. Beloglazkina, E.K., Majouga, A.G., Yudin, I.V., Zyk, N.V., Moiseeva, A.A., and Butin, K.P., Izv. Akad. Nauk, Ser. Khim., 2005, no. 9, p. 2099.

  85. Beloglazkina, E.K., Majouga, A.G., Romashkina, R.B., and Zyk, N.V., Tetrahedron Lett., 2006, vol. 47, no. 14, p. 2957.

    Article  CAS  Google Scholar 

  86. Debdab, M., Renault, S., MaId S., Lozach O., Meijer, L., Carreaux F., and Bazureau, J.P., Heterocycles, 2009, vol. 78, no. 5, p. 1191.

    Article  CAS  Google Scholar 

  87. Khodair, A.I.A., El Ashry, E.S.H., and Al-Masoudi, N.A.L., Monatsh. Chem., 2004, vol. 135, no. 9, p. 1061.

    CAS  Google Scholar 

  88. El Ashry, E.S.H., Awad, L.F., and Atta, A.I., Tetrahedron, 2006, vol. 62, no. 13, p. 2943.

    Article  Google Scholar 

  89. Carrington, H.C. and Waring, W.S., J. Chem. Soc., 1950, p. 354.

  90. Edward, J.T. and Liu, J.K., Can. J. Chem., 1972, no. 50, p. 2423.

  91. Lewis, J.R., Nat. Prod. Rep., 2000, vol. 17, no. 1, p. 57.

    Article  CAS  Google Scholar 

  92. Parmentier, J.-G., Portevin, B., Golsteyn, R.M., Pierre, A., Hickman, J., and Gloanec, P.G., Bioorg. Med. Chem. Lett., 2009, vol. 19, no. 3, p. 841.

    Article  CAS  Google Scholar 

  93. Kandil, S.S., El-Hefnawy, G.B., Bakr, E.A., and El-Ezz, A.Z.A., Transition Met. Chem., 2003, vol. 28, no. 2, p. 168.

    Article  CAS  Google Scholar 

  94. Kandil, S.S., El-Hefnawy, G.B., and Baker, E.A., Thermochim. Acta, 2004, vol. 414, no. 2, p. 105.

    Article  CAS  Google Scholar 

  95. Beloglazkina, E.K., Majouga, A.G., Moiseeva, A.A., and Zyk, N.V., Izv. Akad. Nauk, Ser. Khim., 2007, no. 2, p. 340.

  96. Beloglazkina, E.K., Vatsadze, S.Z., Majouga, A.G., Frolova, N.A., Romashkina, R.B., Zyk, N.V., Moiseeva, A.A., and Butin, K.P., Izv. Akad. Nauk, Ser. Khim., 2005, no. 12, p. 2679.

  97. Majouga, A.G., Beloglazkina, E.K., Vatsadze, S.Z., Moiseeva, A.A., Butin, K.P., and Zyk, N.V., Mendeleev Commun., 2004, vol. 14, no. 3, p. 115.

    Article  Google Scholar 

  98. Beloglazkina, E.K., Majouga, A.G., Romashkina, R.B., Moiseeva, A.A., and Zyk, N.V., Polyhedron, 2007, vol. 26, no. 4, p. 797.

    Article  CAS  Google Scholar 

  99. Majouga, A.G., Beloglazkina, E.K., Shilova, O.V., Moiseeva, A.A., and Zyk, N.V., Izv. Akad. Nauk, Ser. Khim., 2009, no. 7, p. 1353.

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  1. Department of Chemistry, Moscow State University, Moscow, 119992, Russia

    E. K. Beloglazkina, A. G. Majouga, E. A. Manzhelii, N. V. Zyk & N. S. Zefirov

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  1. E. K. Beloglazkina
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Original Russian Text © E.K. Beloglazkina, A.G. Majouga, E.A. Manzhelii, N.V. Zyk, N.S. Zefirov, 2011, published in Obzornyi Zhurnal po Khimii, 2011, Vol. 1, No. 4, pp. 299–333.

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Beloglazkina, E.K., Majouga, A.G., Manzhelii, E.A. et al. 2-Thioxo-tetrahydro-4H-imidazol-4-ones, 2-alkylthio-3,5-dihydro-4H-imidazol-4-ones and their coordination compounds with transition metal ions. Ref. J. Chem. 1, 309–343 (2011). https://doi.org/10.1134/S2079978011020014

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