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3,4-Disubstituted maleimides: synthesis and biological activity

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Chemistry of Heterocyclic Compounds Aims and scope

This review is devoted to methods for the synthesis of 3,4-disubstituted maleimides – compounds that often show pronounced biological activity. We offer classification of synthetic methods, present comparative analysis of various approaches while describing their advantages and drawbacks. The areas of practical applications are indicated for several 3,4-disubstituted maleimide derivatives in the role of pharmaceutical agents or reactive dyes. The majority of the considered publications are from the last 10 years.

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References

  1. Grant, S. K. Cell. Mol. Life Sci. 2009, 66, 1163.

    Article  CAS  Google Scholar 

  2. Fabbro, D.; Cowan-Jacob, S.W.; Möbitz, H.; Martiny-Baron, G. Methods Mol. Biol. 2012, 795, 1.

    Article  CAS  Google Scholar 

  3. Kumar, M. M. K.; Naik, J. D.; Satyavathi, K; Ramana, H.; Varma, P. R.; Nagasree, K. P.; Smitha, D.; Rao, D. V. Nat. Prod. Res. 2014, 28, 888.

    Article  Google Scholar 

  4. Yang, K.; Chen, Y.; Kin, K.; To, K. K. W.; Wang, F.; Li, D.; Chen, L.; Fu, L. Exp. Mol. Med. 2017, 49, e303.

  5. Roskoski, R. Pharm. Res. 2015, 100, 1.

    Article  CAS  Google Scholar 

  6. Cohen, P. Nat. Rev. Drug Discovery 2002, 1, 309.

    Article  CAS  Google Scholar 

  7. Zhang, J.; Yang, P. L.; Gray, N. S. Nat. Rev. Cancer 2009, 9, 28.

    Article  Google Scholar 

  8. Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchya, H.; Takahashi, Y.; Masuma, R. J. Antibiot. 1977, 30, 275.

    Article  CAS  Google Scholar 

  9. Nakanishi, S.; Matsuda, Y.; Iwahashi, K.; Kase, H. J. Antibiot. 1986, 39, 1066.

    Article  CAS  Google Scholar 

  10. Nettleton, D. E.; Doyle, T. W.; Krishnan, B.; Matsumoto, G. K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4011.

    Article  CAS  Google Scholar 

  11. Bush, J. A.; Long, В. H.; Catino, J. J.; Bradner, W. T.; Tomita, K. J. Antibiot. 1987, 40, 668.

  12. Yamashita, Y.; Fujii, N.; Murakata, C.; Ashizawa, Т.; Okabe, M.; Nakano, H. Biochemistry 1992, 31, 12069.

  13. Anizon, F.; Golsteyn, R. M.; Léonce, S.; Pfeiffer, B.; Prudhomme, M. Eur. J. Med. Chem. 2009, 44, 2234.

    Article  CAS  Google Scholar 

  14. Goekjian, P. G.; Jirousek, M. R. Curr. Med. Chem. 1999, 6, 877.

    CAS  Google Scholar 

  15. Merkel, A. L.; Meggers, E.; Ocker, M. Expert Opin. Invest. Drugs 2012, 21, 425.

    Article  CAS  Google Scholar 

  16. Gani, S. M.; Engh, R. A. Nat. Prod. Rep. 2010, 27, 489.

    Article  CAS  Google Scholar 

  17. Smith, D. G.; Buffet, M.; Fenwick, A. E.; Haigh, D.; Ife, R. J.; Saunders, M.; Slingsby, B. P.; Stacey, R.; Ward, R. W. Bioorg. Med. Chem. Lett. 2001, 11, 635.

    Article  CAS  Google Scholar 

  18. Arfeen, M.; Bharatam, P. V. Curr. Pharm. Des. 2013, 19, 4755.

    Article  CAS  Google Scholar 

  19. Phiel, C. J.; Klein, P. S. Annu. Rev. Pharmacol. Toxicol. 2001, 41, 789.

    Article  CAS  Google Scholar 

  20. Wada, A. J. Pharmacol. Sci. 2009, 110, 14.

    Article  CAS  Google Scholar 

  21. Belikov, M. Yu.; Ievlev, M. Yu.; Fedoseev, S. V.; Ershov, O. V. Russ. J. Org. Chem. 2017, 53, 141. [Zh. Org. Khim. 2017, 53, 142.]

  22. Zhao, Y.; Lin, Z.; Zhou, Z.; Yao, H.; Lv, W.; Zhen, H.; Ling, Q. Org. Electron. 2016, 31, 183.

    Article  CAS  Google Scholar 

  23. Shepelenko, E. N.; Makarova, N. I.; Karamov, O. G.; Dubonosov, A. D.; Podshibakin, V. A.; Metelitsa, A. V.; Bren', V. A.; Minkin, V. I. Chem. Heterocycl. Compd. 2014, 50, 932. [Khim. Geterotsikl. Soedin. 2014, 1013.]

  24. Xie, H.-D.; Ho, L. A.; Truelove, M. S.; Corry, B.; Stewart, S. G. J. Fluoresc. 2010, 20, 1077.

    Article  CAS  Google Scholar 

  25. Mei, X.; Wei, K.; Wen, G.; Liu, Z.; Lin, Z.; Zhou, Z.; Huang, L.; Yang, E.; Ling, Q. Dyes Pigm. 2016, 133, 345.

    Article  CAS  Google Scholar 

  26. Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. J. Org. Chem. 1998, 63, 6053.

    Article  CAS  Google Scholar 

  27. Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. Tetrahedron Lett. 1999, 40, 1109.

    Article  CAS  Google Scholar 

  28. Ye, Q.; Li, M.; Zhou, Y.-B.; Cao, J.-Y.; Xu, L.; Li, Y.-J.; Han, L.; Gao, J.-R.; Hu, Y.-Z.; Li, J. Arch. Pharm. 2013, 346, 349.

    Article  CAS  Google Scholar 

  29. Piers, E.; Britton, R.; Andersen, R. J. J. Org. Chem. 2000, 65, 530.

    Article  CAS  Google Scholar 

  30. Levy, D. E.; Wang, D.-X.; Lu, Q.; Chen, Z.; Perumattam, J.; Xu, Y.-J.; Liclican, A.; Higaki, J.; Dong, H.; Laney, M.; Mavunkel, B.; Dugar, S. Bioorg. Med. Chem. Lett. 2008, 18, 2390.

    Article  CAS  Google Scholar 

  31. Levy, D. E.; Wang, D.-X.; Lu, Q.; Chen, Z.; Perumattam, J.; Xu, Y.-J.; Higaki, J.; Dong, H.; Liclican, A.; Laney, M.; Mavunkel, B.; Dugar, S. Bioorg. Med. Chem. Lett. 2008, 18, 2395.

    Article  CAS  Google Scholar 

  32. Lu, Q.; Chen, Z.; Perumattam, J.; Wang, D.-X.; Liang, W.; Xu, Y.-J.; Do, S.; Bonaga, L.; Higaki, J.; Dong, H.; Liclican, A.; Sideris, S.; Laney, M.; Dugar, S.; Mavunkel, B.; Levy, D. E. Bioorg. Med. Chem. Lett. 2008, 18, 2399.

    Article  CAS  Google Scholar 

  33. Peifer, C.; Stoiber, T.; Unger, E.; Totzke, F.; Schächtele, C.; Marmé, D.; Brenk, R.; Klebe, G.; Schollmeyer, D.; Dannhardt, G. J. Med. Chem. 2006, 49, 1271.

    Article  CAS  Google Scholar 

  34. Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; McCroskey, R. W.; Hannick, S. M.; Gherke, L.; Credo, R. B.; Hui, Y.-H.; Marsh, K.; Warner, R.; Lee, J. Y.; Zielinski-Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. J. Med. Chem. 2002, 45, 1697.

    Article  CAS  Google Scholar 

  35. Zhang, H.-С.; Derian, C. K.; McComsey, D. F.; White, K. B.; Ye, H.; Hecker, L. R.; Li, J.; Addo, M. F.; Croll, D.; Eckardt, A. J.; Smith, C. E.; Li, Q.; Cheung, W.-M.; Conway, B. R.; Emanuel, S.; Demarest, K. T.; Andrade-Gordon, P.; Damiano, B. P.; Maryanoff, B. E. J. Med. Chem. 2005, 48, 1725.

    Article  CAS  Google Scholar 

  36. Embi, N.; Rylatt, D. B.; Cohen, P. Eur. J. Biochem. 1980, 107, 519.

    Article  CAS  Google Scholar 

  37. Woodgett, J. R. EMBO J. 1990, 9, 2431.

    CAS  Google Scholar 

  38. Tanaka, M.; Sagawa, S.; Hoshi, J.-I.; Shimoma, F.; Yasue, K.; Ubukata, M.; Ikemoto, T.; Hase, Y.; Takahashi, M.; Sasase, T.; Ueda, N.; Matsushita, M.; Inaba, T. Bioorg. Med. Chem. 2006, 14, 5781.

    Article  CAS  Google Scholar 

  39. Teruyuki, K.; Masato, N.; Yasuyuki, U.; Kenji, W.; Take-aki, M. J. Am. Chem. Soc. 2006, 128, 14816.

    Article  Google Scholar 

  40. Prateeptongkum, S.; Driller, K. M.; Jackstell, R.; Spannenberg, A.; Beller, M. Chem.–Eur. J. 2010, 16, 9606.

    Article  CAS  Google Scholar 

  41. Zhu, F.; Li, Y.; Wang, Z.; Wu, X.-F. ChemCatChem 2016, 8, 3710.

  42. Hu, W.; Zheng, J.; Li, J.; Liu, B.; Wu, W.; Liu, H.; Jiang, H. J. Org. Chem. 2016, 81, 12451.

    Article  CAS  Google Scholar 

  43. (a) Yeh, H.-C.; Wu, W.-C.; Chen, C.-T. Chem. Commun. 2003, 404. (b) Yeh, H.-C.; Wu, W.-C.; Wen, Y.-S.; Dai, D.-C.; Wang, J.-K.; Chen, C.-T. J. Org. Chem. 2004, 69, 6455.

  44. Gao, Q.; Liu, S.; Wu, X.; Wu, A. Tetrahedron Lett. 2014, 55, 6403.

  45. De Risi, C.; Pollini, G. P.; Zanirato, V. Chem. Rev. 2016, 116, 3241.

  46. Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447.

    Article  CAS  Google Scholar 

  47. Basavaiah, D.; Lenin, D. V.; Veeraraghavaiah, G. Curr. Sci. 2011, 101, 888.

    CAS  Google Scholar 

  48. Bouissane, L.; Sestelo, J. P., Sarandeses, L. A. Org. Lett. 2009, 11, 1285.

    Article  CAS  Google Scholar 

  49. Ciamician, G. L.; Silber, P. Chem. Ber. 1884, 17, 553.

    Article  Google Scholar 

  50. Scharf, H. D.; Korte, F. Chem. Ber. 1965, 98, 764.

    Article  CAS  Google Scholar 

  51. (a) Lakatosh, S. A.; Bykov, E. E.; Preobrazhenskaya, M. N. Chem. Heterocycl. Compd. 2011, 46, 1224. [Khim. Geterotsikl. Soedin. 2010, 1515.] (b) Lakatosh, S. A.; Luzikov, Y. N.; Preobrazhenskaya, M. N. Tetrahedron 2005, 61, 8241.

  52. Awuah, E.; Capretta, A. J. Org. Chem. 2011, 76, 3122.

    Article  CAS  Google Scholar 

  53. Wu, P.; Hu, Y. Synth. Commun. 2008, 39, 70.

  54. Mahboobi, S.; Eichhorn, E.; Popp, A.; Sellmer, A.; Elz, S.; Möllmann, U. Eur. J. Med. Chem. 2006, 41, 176.

    Article  CAS  Google Scholar 

  55. Shorunov, S. V.; Krayushkin, M. M.; Stoyanovich, F. M.; Irie, M. Russ. J. Org. Chem. 2006, 42, 1490. [Zh. Org. Khim. 2006, 42, 1504.]

  56. Kaur, A. D. M.Sci. Thesis; Thapar University: Patiala, 2013. http://hdl.handle.net/10266/2427.

  57. Baag, Md. M.; Argade, N. P. Synthesis 2006, 1005.

  58. Cheng, C.-F.; Lai, Z.-C.; Lee, Y.-J. Tetrahedron 2008, 64, 4347.

  59. Stewart, S. G.; Polomska, M. E.; Lim, R. W. Tetrahedron Lett. 2007, 48, 2241.

    Article  CAS  Google Scholar 

  60. Lim, L. H.; Zhou, J. Org. Chem. Front. 2015, 2, 775.

    Article  CAS  Google Scholar 

  61. Deore, P. S.; Argade, N. P. Synthesis 2014, 281.

  62. Jafarpour, F.; Shamsianpour, M. RSC Adv. 2016, 6, 103567.

  63. Haval, K. P.; Argade, N. P. J. Org. Chem. 2008, 73, 6936.

    Article  CAS  Google Scholar 

  64. Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. J. Org. Chem. 1999, 64, 2465.

    Article  CAS  Google Scholar 

  65. Krivec, M.; Gazvoda, M.; Kranjc, K.; Polanc, S.; Kočevar, M. J. Org. Chem. 2012, 77, 2857.

    Article  CAS  Google Scholar 

  66. Davis, P. D.; Bit, R. A.; Hurst, S. A. Tetrahedron Lett. 1990, 31, 2353.

    Article  CAS  Google Scholar 

  67. Davis, P. D.; Bit, R. A. Tetrahedron Lett. 1990, 31, 5201.

    Article  CAS  Google Scholar 

  68. Ondruš, V.; Fišera, L.; Bradac, V. ARKIVOC 2001, (v), 60.

  69. Hamad, A. S.; Abed, F. S. IOSR J. Appl. Chem. 2014, 3, 56.

  70. Borah, H. N.; Boruah, R. C.; Sandhu, J. S. J. Chem. Res., Synop. 1998, 272.

  71. Deshpande, S. R.; Maybhate, S. P. Likhite, A. P.; Chaudhary, P. M. Indian J. Chem. 2010, 49B, 487.

    CAS  Google Scholar 

  72. Tevyashova, A. N.; Olsufyeva, E. N.; Preobrazhenskaya, M. N. Russ. Chem. Rev. 2015, 84, 61. [Usp. Khim. 2015, 84, 61.]

  73. Li, T.; Takeoka, S. Int. J. Nanomed. 2013, 8, 3855.

    Google Scholar 

  74. Karoli T., Mamidyala, S. K.; Zuegg, J.; Fry, S. R.; Tee, E. H. L.; Bradford, T. A.; Madala, P. K.; Huang, J. X.; Ramu, S.; Butler, M. S.; Cooper, M. A. Bioorg. Med. Chem. Lett. 2012, 22, 2428.

  75. Firke, S. D.; Bari, S. B. Bioorg. Med. Chem. 2015, 23, 5273.

    Article  CAS  Google Scholar 

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This study was supported by a grant from the Russian Science Foundation (project 16-15-10300).

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Correspondence to Alexey A. Panov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(2), 103–113

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Panov, A.A., Simonov, A.Y., Lavrenov, S.N. et al. 3,4-Disubstituted maleimides: synthesis and biological activity. Chem Heterocycl Comp 54, 103–113 (2018). https://doi.org/10.1007/s10593-018-2240-z

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