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Synthesis and properties of bi- and tricyclic 1,3-thiazoline/thiazolidine assemblies linked by an exocyclic С=С double bond

  • Konstantin L. ObydennovEmail author
  • Tatiana V. Glukhareva
Article
  • 21 Downloads

This review provides a generalized and systematized analysis of literature data from the last 15 years regarding the methods of synthesis and properties of bi- and tricyclic assemblies constructed from 1,3-thiazolidine/thiazoline rings that are linked by an exocyclic С=С double bond. Examples of such assemblies which are of interest as biologically active compounds, sensitizing dyes for solar cells, and semiconductors are considered in details. The literature data have been arranged according to the types of chemical structures.

Keywords

bis(1,3-thiazolinylidenes) 1,3-thiazolidines 1,3-thiazolines rhodacyanines quinoid heterocycles exocyclic double bond,heterocyclic assemblies photovoltaic cells sensitizing dyes semiconductors 

Notes

This review article was prepared with financial support from the Russian Foundation for Basic Research (project No. 18-316-20018) and Act No. 211 of the Government of the Russian Federation, contract No. 02.A03.21.0006.

References

  1. 1.
    Gaumont, A.-C.; Gulea, M.; Levillain, J. Chem. Rev.2009, 109, 1371.PubMedCrossRefGoogle Scholar
  2. 2.
    Jain, A. K.; Vaidya, A.; Ravichandran, V.; Kashaw, S. K.; Agrawal, R. K. Bioorg. Med. Chem.2012, 20, 3378.PubMedCrossRefGoogle Scholar
  3. 3.
    Tripathi, A. C.; Gupta, S. J.; Fatima, G. N.; Sonar, P. K.; Verma, A.; Saraf, S. K. Eur. J. Med. Chem.2014, 72, 52.PubMedCrossRefGoogle Scholar
  4. 4.
    Asati, V.; Mahapatra, D. K.; Bharti, S. K. Eur. J. Med. Chem.2014, 87, 814.PubMedCrossRefGoogle Scholar
  5. 5.
    Stojanovic, M.; Dzambaski, Z.; Bondzic, B.; Aleksic, J.; Baranac-Stojanovic, M. Curr. Org. Chem.2014, 18, 1108.CrossRefGoogle Scholar
  6. 6.
    Rostamnia, S.; Doustkhah, E. in Green Chemistry: Synthesis of Bioactive Heterocycles; Ameta, K. L.; Dandia, A., Eds.; Springer India: New Delhi, 2014, p. 253.Google Scholar
  7. 7.
    Gazieva, G. A.; Izmest'ev, A. N. Chem. Heterocycl. Compd.2015, 50, 1515. [Khim. Geterotsikl. Soedin.2014, 1649.]Google Scholar
  8. 8.
    Havrylyuk, D.; Zimenkovsky, B.; Lesyk, R. Mini-Rev. Org. Chem.2015, 12, 66.CrossRefGoogle Scholar
  9. 9.
    Havrylyuk, D.; Roman, O.; Lesyk, R. Eur. J. Med. Chem.2016, 113, 145.PubMedCrossRefGoogle Scholar
  10. 10.
    Takasu, K. Chem. Pharm. Bull.2016, 64, 656.PubMedCrossRefPubMedCentralGoogle Scholar
  11. 11.
    Lesyk, R.; Zimenkovsky, B. Curr. Org. Chem.2004, 8, 1547.CrossRefGoogle Scholar
  12. 12.
    Tomasic, T.; Masic, L. P. Curr. Med. Chem.2009, 16, 1596.PubMedCrossRefPubMedCentralGoogle Scholar
  13. 13.
    Jain, V. S.; Vora, D. K.; Ramaa, C. S. Bioorg. Med. Chem.2013, 21, 1599.PubMedCrossRefPubMedCentralGoogle Scholar
  14. 14.
    Zhan, P.; Pannecouque, C.; De Clercq, E.; Liu, X. J. Med. Chem.2016, 59, 2849.PubMedCrossRefPubMedCentralGoogle Scholar
  15. 15.
    Naim, M. J.; Alam, M. J.; Ahmad, S.; Nawaz, F.; Shrivastava, N.; Sahu, M.; Alam, O. Eur. J. Med. Chem.2017, 129, 218.PubMedCrossRefPubMedCentralGoogle Scholar
  16. 16.
    Kaur Manjal, S.; Kaur, R.; Bhatia, R.; Kumar, K.; Singh, V.; Shankar, R.; Kaur, R.; Rawal, R. K. Bioorg. Chem.2017, 75, 406.PubMedCrossRefPubMedCentralGoogle Scholar
  17. 17.
    Kaminskyy, D.; Kryshchyshyn, A.; Lesyk, R. Expert Opin. Drug Discovery2017, 12, 1233.CrossRefGoogle Scholar
  18. 18.
    Kaminskyy, D.; Kryshchyshyn, A.; Lesyk, R. Eur. J. Med. Chem.2017, 140, 542.PubMedCrossRefPubMedCentralGoogle Scholar
  19. 19.
    Löscher, W.; Schmidt, D. Epilepsy Res.1994, 17, 95.PubMedCrossRefGoogle Scholar
  20. 20.
    Rizos, C. V.; Kei, A.; Elisaf, M. S. Arch. Toxicol.2016, 90, 1861.PubMedCrossRefPubMedCentralGoogle Scholar
  21. 21.
    Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed.2000, 39, 44.Google Scholar
  22. 22.
    Ramsh, S. M. Guidelines for naming heterocyclic compounds (with examples and excercises) [in Russian]; Khimizdat: St. Petersburg, 2009, p. 321.Google Scholar
  23. 23.
    IUPAC Compendium of Chemical Terminology. http:// goldbook.iupac.org/terms/view/R05393.
  24. 24.
    Matsui, M.; Asamura, Y.; Kubota, Y.; Funabiki, K.; Jin, J.; Yoshida, T.; Miura, H. Tetrahedron2010, 66, 7405.CrossRefGoogle Scholar
  25. 25.
    Matsui, M.; Kotani, M.; Kubota, Y.; Funabiki, K.; Jin, J.; Yoshida, T.; Higashijima, S.; Miura, H. Dyes Pigm.2011, 91, 145.CrossRefGoogle Scholar
  26. 26.
    Matsui, M.; Fujita, T.; Kubota, Y.; Funabiki, K.; Jin, J.; Yoshida, T.; Miura, H. Dyes Pigm.2010, 86, 143.CrossRefGoogle Scholar
  27. 27.
    Matsui, M.; Shiota, T.; Kubota, Y.; Funabiki, K.; Jin, J.; Yoshida, T.; Higashijima, S.; Miura, H. Tetrahedron2012, 68, 4286.CrossRefGoogle Scholar
  28. 28.
    Matsui, M.; Inoue, T.; Ono, M.; Kubota, Y.; Funabiki, K.; Jin, J.; Yoshida, T.; Higashijima, S.; Miura, H. Dyes Pigm.2013, 96, 614.CrossRefGoogle Scholar
  29. 29.
    Mishra, A.; Fischer, M. K. R.; Bäuerle, P. Angew. Chem., Int. Ed.2009, 48, 2474.Google Scholar
  30. 30.
    Brogdon, P.; Cheema, H.; Delcamp, J. H. ChemSusChem2018, 11, 86.PubMedCrossRefPubMedCentralGoogle Scholar
  31. 31.
    Lorcy, D.; Bellec, N. Chem. Rev.2004, 104, 5185.PubMedCrossRefPubMedCentralGoogle Scholar
  32. 32.
    Toplak, R.; Bénard-Rocherullé, P.; Lorcy, D. Tetrahedron Lett.2002, 43, 3879.CrossRefGoogle Scholar
  33. 33.
    Eid, S.; Guerro, M.; Roisnel, T.; Lorcy, D. Org. Lett.2006, 8, 2377.PubMedCrossRefPubMedCentralGoogle Scholar
  34. 34.
    Bellec, N.; Lorcy, D.; Robert, A.; Carlier, R.; Tallec, A. J. Electroanal. Chem.1999, 462, 137.CrossRefGoogle Scholar
  35. 35.
    Guérin, D.; Carlier, R.; Guerro, M.; Lorcy, D. Tetrahedron2003, 59, 5273.CrossRefGoogle Scholar
  36. 36.
    Olivier, C.; Toplak, R.; Guerro, M.; Carlier, R.; Lorcy, D. C. R. Chim.2005, 8, 235.Google Scholar
  37. 37.
    Arduengo, A. J.; Goerlich, J. R.; Marshall, W. J. Liebigs Ann.1997, 365.Google Scholar
  38. 38.
    Suzuki, K.; Tomura, M.; Tanaka, S.; Yamashita, Y. Tetrahedron Lett.2000, 41, 8359.CrossRefGoogle Scholar
  39. 39.
    Suzuki, K.; Tomura, M.; Tanaka, S.; Yamashita, Y. CCDC 154534: Experimental Crystal Structure Determination; 2001. DOI:  https://doi.org/10.5517/cc55sz2.
  40. 40.
    Iijima, K.; Le Gal, Y.; Higashino, T.; Lorcy, D.; Mori, T. J. Mater. Chem. C2017, 5, 9121.CrossRefGoogle Scholar
  41. 41.
    Iijima, K.; Le Gal, Y.; Higashino, T.; Lorcy, D.; Mori, T. CCDC 1558710: Experimental Crystal Structure Determination; 2017. DOI:  https://doi.org/10.5517/ccdc.csd.cc1p9yzx.
  42. 42.
    Matsui, M.; Fujita, T.; Kubota, Y.; Funabiki, K.; Miura, H.; Shiro, M. CCDC 762266: Experimental Crystal Structure Determination; 2010. DOI:  https://doi.org/10.5517/cctl67t.
  43. 43.
    Matsui, M.; Fujita, T.; Kubota, Y.; Funabiki, K.; Miura, H.; Shiro, M. Bull. Chem. Soc. Jpn.2010, 83, 709.Google Scholar
  44. 45.
    Le Gal, Y.; Rajkumar, M.; Vacher, A.; Dorcet, V.; Roisnel, T.; Fourmigué, M.; Barrière, F.; Guizouarn, T.; Lorcy, D. CCDC 1471695: Experimental Crystal Structure Determination; 2016. DOI:  https://doi.org/10.5517/ccdc.csd.cc1ldf1g.
  45. 46.
    Le Gal, Y.; Rajkumar, M.; Vacher, A.; Dorcet, V.; Roisnel, T.; Fourmigué, M.; Barrière, F.; Guizouarn, T.; Lorcy, D. CrystEngComm2016, 18, 3925.CrossRefGoogle Scholar
  46. 47.
    Baranac-Stojanović, M.; Kleinpeter, E. J. Org. Chem.2011, 76, 3861.PubMedCrossRefGoogle Scholar
  47. 48.
    Baranac-Stojanović, M.; Klaumünzer, U.; Marković, R.; Kleinpeter, E. Tetrahedron2010, 66, 8958.CrossRefGoogle Scholar
  48. 49.
    Rašović, A.; Blagojević, V.; Baranac-Stojanović, M.; Kleinpeter, E.; Marković, R.; Minić, D. M. New J. Chem.2016, 40, 6364.Google Scholar
  49. 50.
    Marković, R.; Baranac, M.; Juranić, N.; Macura, S.; Cekić, I.; Minić, D. J. Mol. Struct.2006, 800, 85.CrossRefGoogle Scholar
  50. 51.
    Kleinpeter, E. J. Serb. Chem. Soc.2006, 71, 1.CrossRefGoogle Scholar
  51. 52.
    Beverina, L.; Pagani, G. A. Acc. Chem. Res.2014, 47, 319.PubMedCrossRefGoogle Scholar
  52. 53.
    Ye, G.; Chatterjee, S.; Li, M.; Zhou, A.; Song, Y.; Barker, B. L.; Chen, C.; Beard, D. J.; Henry, W. P.; Pittman, C. U. Tetrahedron2010, 66, 2919.CrossRefGoogle Scholar
  53. 54.
    Rattananakin, P.; Pittman, C. U.; Collier, W. E.; Saebø, S. Struct. Chem.2007, 18, 399.CrossRefGoogle Scholar
  54. 55.
    Kleinpeter, E.; Klod, S.; Rudorf, W.-D. J. Org. Chem.2004, 69, 4317.PubMedCrossRefGoogle Scholar
  55. 56.
    Kleinpeter, E.; Koch, A.; Heydenreich, M.; Chatterjee, S. K.; Rudorf, W.-D. J. Mol. Struct.1995, 356, 25.CrossRefGoogle Scholar
  56. 57.
    Mueller, J. L.; Gibson, M. S.; Hartman, J. S. Can. J. Chem.1996, 74, 1329.CrossRefGoogle Scholar
  57. 58.
    Kleinpeter, E.; Heydenreich, M.; Woller, J.; Wolf, G.; Koch, A.; Kempter, G.; Pihlaja, K. J. Chem. Soc., Perkin Trans. 21998, 1877.Google Scholar
  58. 59.
    Meier, H.; Mühling, B.; Gerold, J.; Jacob, D.; Oehlhof, A. Eur. J. Org. Chem.2007, 625.CrossRefGoogle Scholar
  59. 60.
    Kleinpeter, E.; Schulenburg, A. Tetrahedron Lett.2005, 46, 5995.CrossRefGoogle Scholar
  60. 61.
    Kalogirou, A. S.; Michaelidou, S. S.; White, A. J. P.; Panayiotis, A. K. CCDC 1036126: Experimental Crystal Structure Determination; 2015. DOI:  https://doi.org/10.5517/cc13s5fh.
  61. 62.
    Kalogirou, A. S.; Michaelidou, S. S.; White, A. J. P.; Koutentis, P. A. Tetrahedron2015, 71, 1799.CrossRefGoogle Scholar
  62. 63.
    Minkin, V. I.; Minyaev, R. M. Chem. Rev. 2001, 101, 1247.PubMedCrossRefGoogle Scholar
  63. 64.
    Iijima, K.; Le Gal, Y.; Higashino, T.; Lorcy, D.; Mori, T. CCDC 1558720: Experimental Crystal Structure Determination; 2017. DOI:  https://doi.org/10.5517/ccdc.csd.cc1p9z98.
  64. 65.
    Iijima, K.; Le Gal, Y.; Higashino, T.; Lorcy, D.; Mori, T. CCDC 1558721: Experimental Crystal Structure Determination; 2017. DOI:  https://doi.org/10.5517/ccdc.csd.cc1p9zb9.
  65. 66.
    Iijima, K.; Le Gal, Y.; Higashino, T.; Lorcy, D.; Mori, T. CCDC 1558721: Experimental Crystal Structure Determination; 2017. DOI:  https://doi.org/10.5517/ccdc.csd.cc1p9zfd.
  66. 67.
    Aragoni, M. C.; Arca, M.; Devillanova, F. A.; Isaia, F.; Lippolis, V.; Mancini, A.; Pala, L.; Slawin, A. M. Z.; Woollins, J. D. CCDC 262774: Experimental Crystal Structure Determination; 2006. DOI:  https://doi.org/10.5517/cc8tfl2.
  67. 68.
    Aragoni, M. C.; Arca, M.; Devillanova, F. A.; Isaia, F.; Lippolis, V.; Mancini, A.; Pala, L.; Slawin, A. M. Z.; Woollins, J. D. Inorg. Chem.2005, 44, 9610.PubMedCrossRefGoogle Scholar
  68. 69.
    Le Gal, Y.; Bellec, N.; Barrière, F.; Clérac, R.; Fourmigué, M.; Dorcet, V.; Roisnel, T.; Lorcy, D. CCDC 951711: Experimental Crystal Structure Determination; 2013. DOI:  https://doi.org/10.5517/cc10ybcn.
  69. 70.
    Le Gal, Y.; Bellec, N.; Barrière, F.; Clérac, R.; Fourmigué, M.; Dorcet, V.; Roisnel, T.; Lorcy, D. Dalton Trans.2013, 42, 16672.PubMedCrossRefGoogle Scholar
  70. 71.
    Iijima, K.; Le Gal, Y.; Higashino, T.; Lorcy, D.; Mori, T. CCDC 1558711: Experimental Crystal Structure Determination; 2017. DOI:  https://doi.org/10.5517/ccdc.csd.cc1p9z0z.
  71. 72.
    Abd-Elmalek, H. A. CCDC 830679: Experimental Crystal Structure Determination; 2012. DOI:  https://doi.org/10.5517/ccwwd37.
  72. 73.
    Abdel-Malek, H. A. Phosphorus, Sulfur Silicon Relat. Elem.2012, 187, 506.Google Scholar
  73. 74.
    Le Gal, Y.; Rajkumar, M.; Vacher, A.; Dorcet, V.; Roisnel, T.; Fourmigué, M.; Barrière, F.; Guizouarn, T.; Lorcy, D. CCDC 1471698: Experimental Crystal Structure Determination; 2016. DOI:  https://doi.org/10.5517/ccdc.csd.cc1ldf4k.
  74. 75.
    Morel, G.; Gachot, G.; Lorcy, D. CCDC 259963: Experimental Crystal Structure Determination; 2005. DOI:  https://doi.org/10.5517/cc8qhxc.
  75. 76.
    Morel, G.; Gachot, G.; Lorcy, D. Synlett2005, 1117.Google Scholar
  76. 77.
    Le Gal, Y.; Bellec, N.; Barrière, F.; Clérac, R.; Fourmigué, M.; Dorcet, V.; Roisnel, T.; Lorcy, D. CCDC 951710: Experimental Crystal Structure Determination; 2013. DOI:  https://doi.org/10.5517/cc10ybbm.
  77. 79.
    Baryshnikov, G. V.; Minaev, B. F.; Minaeva, V. A.; Baryshnikova, A. T. J. Struct. Chem.2012, 53, 428.CrossRefGoogle Scholar
  78. 80.
    Wang, H.-Y.; Cui, L.; Xie, J.-Z.; Leong, C. F.; D'Alessandro, D. M.; Zuo, J.-L. Coord. Chem. Rev.2017, 345, 342.CrossRefGoogle Scholar
  79. 81.
    Nakazawa, Y.; Imajo, S.; Matsumura, Y.; Yamashita, S.; Akutsu, H. Crystals2018, 8, 143.CrossRefGoogle Scholar
  80. 82.
    Doni, E.; Murphy, J. A. Chem. Commun. (Cambridge, U. K.)2014, 50, 6073.Google Scholar
  81. 83.
    Le Gal, Y.; Ameline, D.; Bellec, N.; Vacher, A.; Roisnel, T.; Dorcet, V.; Jeannin, O.; Lorcy, D. Org. Biomol. Chem.2015, 13, 8479.PubMedCrossRefGoogle Scholar
  82. 84.
    Tormos, G. V.; Bakker, M. G.; Wang, P.; Lakshmikantham, M. V.; Cava, M. P.; Metzger, R. M. J. Am. Chem. Soc.1995, 117, 8528.CrossRefGoogle Scholar
  83. 85.
    Wang, H.-J.; Shi, J.; Fang, M.; Li, Z.; Guo, Q.-X. J. Phys. Org. Chem.2010, 23, 75.Google Scholar
  84. 86.
    Bellec, N.; Lorcy, D.; Robert, A.; Carlier, R.; Tallec, A.; Rimbaud, C.; Ouahab, L.; Clerac, R.; Delhaes, P. Adv. Mater.1997, 9, 1052.CrossRefGoogle Scholar
  85. 87.
    Bellec, N.; Guérin, D.; Lorcy, D.; Robert, A.; Carlier, R.; Tallec, A.; Shono, T.; Toftlund, H. Acta Chem. Scand.1999, 53, 861.CrossRefGoogle Scholar
  86. 88.
    Pérez-Perarnau, A.; Preciado, S.; Palmeri, C. M.; Moncunill- Massaguer, C.; Iglesias-Serret, D.; González-Gironès, D. M.; Miguel, M.; Karasawa, S.; Sakamoto, S.; Cosialls, A. M.; Rubio-Patiño, C.; Saura-Esteller, J.; Ramón, R.; Caja, L.; Fabregat, I.; Pons, G.; Handa, H.; Albericio, F.; Gil, J.; Lavilla, R. Angew. Chem., Int. Ed.2014, 53, 10150.Google Scholar
  87. 89.
    Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed.2010, 49, 676.Google Scholar
  88. 90.
    Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun.1984, 932.Google Scholar
  89. 91.
    Charushin, V. N.; Chupakhin, O. N. Mendeleev Commun.2007, 17, 249.CrossRefGoogle Scholar
  90. 92.
    Starodub, V. A.; Starodub, T. N. Russ. Chem. Rev.2014, 83, 391. [Успехи химии2014, 83, 391.]Google Scholar
  91. 93.
    Koyioni, M.; Koutentis, P. A. Org. Lett.2017, 19, 174.PubMedCrossRefPubMedCentralGoogle Scholar
  92. 94.
    Kalogirou, A. S.; Koutentis, P. A. Tetrahedron2009, 65, 6859.CrossRefGoogle Scholar
  93. 95.
    Filatre-Furcate, A.; Higashino, T.; Lorcy, D.; Mori, T. J. Mater. Chem. C2015, 3, 3569.CrossRefGoogle Scholar
  94. 96.
    Le Gal, Y.; Ameline, D.; Vacher, A.; Roisnel, T.; Dorcet, V.; Lorcy, D. New J. Chem.2016, 40, 9930.CrossRefGoogle Scholar
  95. 97.
    Nasiri, F.; Zolali, A.; Asadbegi, S. J. Heterocycl. Chem.2016, 53, 989.CrossRefGoogle Scholar
  96. 98.
    Alizadeh, A.; Rostamnia, S.; Zohreh, N.; Hosseinpour, R. Tetrahedron Lett.2009, 50, 1533.CrossRefGoogle Scholar
  97. 99.
    Iijima, K.; Le Gal, Y.; Lorcy, D.; Mori, T. RSC Adv.2018, 8, 18400.CrossRefGoogle Scholar
  98. 100.
    Zaleska, B.; Burgiel, M. M.; Serda, P. Chem. Heterocycl. Compd.2008, 44, 349. [Khim. Geterotsikl. Soedin.2008, 452.]Google Scholar
  99. 101.
    Metwally, M. A.; Keshk, E. M.; Fekry, A.; Etman, H. A. Phosphorus, Sulfur Silicon Relat. Elem.2004, 179, 2067.CrossRefGoogle Scholar
  100. 102.
    Chaurasia, S.; Lin, J. T. Chem. Rec.2016, 16, 1311.PubMedCrossRefGoogle Scholar
  101. 103.
    Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Chem. Rev.2010, 110, 6595.PubMedCrossRefGoogle Scholar
  102. 104.
    Li, Z.; He, G.; Wan, X.; Liu, Y.; Zhou, J.; Long, G.; Zuo, Y.; Zhang, M.; Chen, Y. Adv. Energy Mater.2012, 2, 74.CrossRefGoogle Scholar
  103. 105.
    Guo, X.; Liao, Q.; Manley, E. F.; Wu, Z.; Wang, Y.; Wang, W.; Yang, T.; Shin, Y.-E.; Cheng, X.; Liang, Y.; Chen, L. X.; Baeg, K.-J.; Marks, T. J.; Guo, X. Chem. Mater.2016, 28, 2449.CrossRefGoogle Scholar
  104. 106.
    Tian, H.; Yang, X.; Chen, R.; Hagfeldt, A.; Sun, L. Energy Environ. Sci.2009, 2, 674.CrossRefGoogle Scholar
  105. 107.
    Wu, G.; Kong, F.; Zhang, Y.; Zhang, X.; Li, J.; Chen, W.; Zhang, C.; Dai, S. Dyes Pigm.2014, 105, 1.CrossRefGoogle Scholar
  106. 108.
    Cheng, H.-M.; Hsieh, W.-F. Energy Environ. Sci.2010, 3, 442.CrossRefGoogle Scholar
  107. 109.
    Le Bahers, T.; Pauporté, T.; Scalmani, G.; Adamo, C.; Ciofini, I. Phys. Chem. Chem. Phys.2009, 11, 11276.PubMedCrossRefGoogle Scholar
  108. 110.
    Xu, J.; Liang, G.; Wang, L.; Xu, W.; Cui, W.; Zhang, H.; Li, Z. J. Serb. Chem. Soc.2010, 75, 259.CrossRefGoogle Scholar
  109. 111.
    Ren, X.-F.; Zhang, J.; Kang, G.-J. J. Nanomaterials2015, 605728.Google Scholar
  110. 112.
    Ham, H. W.; Kim, Y. S. Thin Solid Films2010, 518, 6558.CrossRefGoogle Scholar
  111. 113.
    Mee, J. D. US Patent 5679795.Google Scholar
  112. 114.
    He, G.; Li, Z.; Wan, X.; Liu, Y.; Zhou, J.; Long, G.; Zhang, M.; Chen, Y. J. Mater. Chem.2012, 22, 9173.CrossRefGoogle Scholar
  113. 115.
    Bahrami, K.; Khodaei, M. M.; Farrokhi, A. Tetrahedron2009, 65, 7658.CrossRefGoogle Scholar
  114. 116.
    Higashijima, S.; Miura, H.; Fujita, T.; Kubota, Y.; Funabiki, K.; Yoshida, T.; Matsui, M. Tetrahedron2011, 67, 6289.CrossRefGoogle Scholar
  115. 117.
    Matsui, M.; Tanaka, N.; Kubota, Y.; Funabiki, K.; Jin, J.; Higashijima, S.; Miura, H.; Manseki, K. RSC Adv.2016, 6, 33111.CrossRefGoogle Scholar
  116. 118.
    Kuang, D.; Uchida, S.; Humphry-Baker, R.; Zakeeruddin, S. M.; Grätzel, M. Angew. Chem., Int. Ed.2008, 47, 1923.Google Scholar
  117. 119.
    Ito, S.; Zakeeruddin, S. M.; Humphry-Baker, R.; Liska, P.; Charvet, R.; Comte, P.; Nazeeruddin, M. K.; Péchy, P.; Takata, M.; Miura, H.; Uchida, S.; Grätzel, M. Adv. Mater.2006, 18, 1202.CrossRefGoogle Scholar
  118. 120.
    Horiuchi, T.; Miura, H.; Sumioka, K.; Uchida, S. J. Am. Chem. Soc.2004, 126, 12218.PubMedCrossRefGoogle Scholar
  119. 121.
    Onwona-Agyeman, B.; Nakao, M.; Asoka Kumara, G. R. J. Mater. Res.2010, 25, 1838.CrossRefGoogle Scholar
  120. 122.
    Lin, R. Y.-Y.; Lee, C.-P.; Chen, Y.-C.; Peng, J.-D.; Chu, T.-C.; Chou, H.-H.; Yang, H.-M.; Lin, J. T.; Ho, K.-C. Chem. Commun.2012, 48, 12071.CrossRefGoogle Scholar
  121. 123.
    Hosono, E.; Mitsui, Y.; Zhou, H. Dalton Trans.2008, 5439.Google Scholar
  122. 124.
    Chiu, W.-H.; Lee, C.-H.; Cheng, H.-M.; Lin, H.-F.; Liao, S.-C.; Wu, J.-M.; Hsieh, W.-F. Energy Environ. Sci.2009, 2, 694.CrossRefGoogle Scholar
  123. 125.
    Liu, Z.; Ojima, H.; Hong, Z.; Kido, J.; Tian, W.; Wang, X.-F. Molecules2013, 18, 3107.PubMedPubMedCentralCrossRefGoogle Scholar
  124. 126.
    Higashijima, S.; Inoue, Y.; Miura, H.; Kubota, Y.; Funabiki, K.; Yoshida, T.; Matsui, M. RSC Adv.2012, 2, 2721.CrossRefGoogle Scholar
  125. 127.
    Huckaba, A. J.; Yella, A.; McNamara, L. E.; Steen, A. E.; Murphy, J. S.; Carpenter, C. A.; Puneky, G. D.; Hammer, N. I.; Nazeeruddin, M. K.; Grätzel, M.; Delcamp, J. H. Chem.– Eur. J.2016, 22, 15536.Google Scholar
  126. 128.
    Ito, S.; Miura, H.; Uchida, S.; Takata, M.; Sumioka, K.; Liska, P.; Comte, P.; Péchy, P.; Grätzel, M. Chem. Commun.2008, 5194.Google Scholar
  127. 129.
    El-Zohry, A.; Orthaber, A.; Zietz, B. J. Phys. Chem. C2012, 116, 26144.CrossRefGoogle Scholar
  128. 130.
    El-Zohry, A. M.; Zietz, B. J. Phys. Chem. C2013, 117, 6544.CrossRefGoogle Scholar
  129. 131.
    Zietz, B.; Gabrielsson, E.; Johansson, V.; El-Zohry, A. M.; Sun, L.; Kloo, L. Phys. Chem. Chem. Phys.2014, 16, 2251.PubMedCrossRefGoogle Scholar
  130. 132.
    Hassaneen, H. M.; Miqdad, O. A.; Abunada, N. M.; Fares, A. A. Nat. Sci. (Irvine, CA, U. S.)2011, 3, 199.Google Scholar
  131. 133.
    Salem, M. A. Croat. Chem. Acta2017, 90, 7.CrossRefGoogle Scholar
  132. 134.
    Hahnemann, C.; Hartmann, H. Helv. Chim. Acta2003, 86, 1949.CrossRefGoogle Scholar
  133. 135.
    Kawakami, M.; Koya, K.; Ukai, T.; Tatsuta, N.; Ikegawa, A.; Ogawa, K.; Shishido, T.; Chen, L. B. J. Med. Chem.1997, 40, 3151.PubMedCrossRefGoogle Scholar
  134. 136.
    Kulinich, A. V; Ishchenko, A. A. Russ. Chem. Rev.2009, 78,Google Scholar
  135. 137.
    [Usp. Khim.2009, 78, 151.]Google Scholar
  136. 138.
    Shindy, H. Mini. Rev. Org. Chem.2012, 9, 352.CrossRefGoogle Scholar
  137. 139.
    Wong, J. R.; Chen1, L. B.; Hu, J.; Garlid, K. D. Cancer Res.1994, 54, 1465.Google Scholar
  138. 140.
    Dairkee, S. H.; Deng, G.; Stampfer, M.; Waldman, F. M.; Smith, H. S. Cancer Res.1995, 55, 2516.PubMedGoogle Scholar
  139. 141.
    Koya, K.; Li, Y.; Wang, H.; Ukai, T.; Tatsuta, N.; Kawakami, M.; Shishido, T.; Chen, L. B. Cancer Res.1996, 56, 538.PubMedGoogle Scholar
  140. 142.
    Kawakami, M.; Koya, K.; Ukai, T.; Tatsuta, N.; Ikegawa, A.; Ogawa, K.; Shishido, T.; Chen, L. B. J. Med. Chem.1998, 41, 130.PubMedCrossRefGoogle Scholar
  141. 143.
    Weisberg, E. L.; Koya, K.; Modica-Napolitano, J.; Li, Y.; Chen, L. B. Cancer Res.1996, 56, 551.PubMedGoogle Scholar
  142. 141.
    Britten, C. D.; Rowinsky, E. K.; Baker, S. D.; Weiss, G. R.; Smith, L.; Stephenson, J.; Rothenberg, M.; Smetzer, L.; Cramer, J.; Collins, W.; Von Hoff, D. D.; Eckhardt, S. G. Clin. Cancer Res.2000, 6, 42.PubMedGoogle Scholar
  143. 142.
    Propper, D. J.; Braybrooke, J. P.; Taylor, D. J.; Lodi, R.; Styles, P.; Cramer, J. A.; Collins, W. C. J.; Levitt, N. C.; Talbot, D. C.; Ganesan, T. S.; Harris, A. L. Ann. Oncol.1999, 10, 923.PubMedCrossRefGoogle Scholar
  144. 143.
    Tatsuta, N.; Suzuki, N.; Mochizuki, T.; Koya, K.; Kawakami, M.; Shishido, T.; Motoji, N.; Kuroiwa, H.; Shigematsu, A.; Chen, L. B. Cancer Chemother. Pharmacol.1999, 43, 295.PubMedCrossRefGoogle Scholar
  145. 144.
    Takasu, K. Chem. Pharm. Bull.2016, 64, 656.PubMedCrossRefPubMedCentralGoogle Scholar
  146. 145.
    Takasu, K.; Inoue, H.; Kim, H.-S.; Suzuki, M.; Shishido, T.; Wataya, Y.; Ihara, M. J. Med. Chem.2002, 45, 995.PubMedCrossRefGoogle Scholar
  147. 146.
    Kendall, J. D.; Suggate, H. G. J. Chem. Soc.1949, 1503.Google Scholar
  148. 147.
    Takasu, K.; Terauchi, H.; Inoue, H.; Kim, H.-S.; Wataya, Y.; Ihara, M. J. Comb. Chem.2003, 5, 211.PubMedCrossRefGoogle Scholar
  149. 148.
    Takasu, K.; Terauchi, H.; Inoue, H.; Takahashi, M.; Sekita, S.; Ihara, M. Heterocycles2004, 64, 215.CrossRefGoogle Scholar
  150. 149.
    Li, X.; Srinivasan, S. R.; Connarn, J.; Ahmad, A.; Young, Z. T.; Kabza, A. M.; Zuiderweg, E. R. P.; Sun, D.; Gestwicki, J. E. ACS Med. Chem. Lett.2013, 4, 1042.PubMedCentralCrossRefPubMedGoogle Scholar
  151. 150.
    Xiang, J.-F.; Liu, Y.-X.; Sun, D.; Zhang, S.-J.; Fu, Y.-L.; Zhang, X.-H.; Wang, L.-Y. Dyes Pigm.2012, 93, 1481.CrossRefGoogle Scholar
  152. 151.
    Li, Y. X.; Zhai, X.; Liao, W. K.; Zhu, W. F.; He, Y.; Gong, P. Chin. Chem. Lett.2012, 23, 415.CrossRefGoogle Scholar
  153. 152.
    Miyata, Y.; Li, X.; Lee, H.-F.; Jinwal, U. K.; Srinivasan, S. R.; Seguin, S. P.; Young, Z. T.; Brodsky, J. L.; Dickey, C. A.; Sun, D.; Gestwicki, J. E. ACS Chem. Neurosci.2013, 4, 930.PubMedPubMedCentralCrossRefGoogle Scholar
  154. 153.
    Wang, A. M.; Miyata, Y.; Klinedinst, S.; Peng, H.-M.; Chua, J. P.; Komiyama, T.; Li, X.; Morishima, Y.; Merry, D. E.; Pratt, W. B.; Osawa, Y.; Collins, C. A.; Gestwicki, J. E.; Lieberman, A. P. Nat. Chem. Biol.2013, 9, 112.PubMedCrossRefPubMedCentralGoogle Scholar
  155. 154.
    Pudhom, K.; Kasai, K.; Terauchi, H.; Inoue, H.; Kaiser, M.; Brun, R.; Ihara, M.; Takasu, K. Bioorg. Med. Chem.2006, 14, 8550.PubMedCrossRefPubMedCentralGoogle Scholar
  156. 155.
    Takasu, K.; Pudhom, K.; Kaiser, M.; Brun, R.; Ihara, M. J. Med. Chem.2006, 49, 4795.PubMedCrossRefPubMedCentralGoogle Scholar
  157. 156.
    Morisaki, D.; Kim, H.-S.; Inoue, H.; Terauchi, H.; Kuge, S.; Naganuma, A.; Wataya, Y.; Tokuyama, H.; Ihara, M.; Takasu, K. Chem. Sci.2010, 1, 206.CrossRefGoogle Scholar
  158. 157.
    Kasmi-Mir, S.; Zradni, F.-Z.; Rahmouni, M.; Kirsch, G. Mediterr. J. Chem.2014, 2, 719.CrossRefGoogle Scholar
  159. 158.
    Kasmi-Mir, S.; Djafri, A.; Hamelin, J.; Paquin, L.; Bazureau, J. P.; Rahmouni, M. Synth. Commun.2007, 37, 4017.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Konstantin L. Obydennov
    • 1
    Email author
  • Tatiana V. Glukhareva
    • 1
    • 2
  1. 1.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia

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