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Ureas bearing alkylaromatic moieties: their synthesis and biological activity

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Abstract

The review presents and summarizes comprehensive data starting from 2000 on the synthesis of ureas containing alkylaromatic moieties. The advantages and drawbacks of various synthetic methods were highlighted. The biological activity was covered for some representatives of this class of compounds.

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References

  1. E. W. Schmidt, M. K. Harper, D. J. Faulkner, J. Nat. Prod., 1997, 60, 779.

    Article  CAS  Google Scholar 

  2. T. Sano, K. Kaya, Tetrahedron Lett., 1995, 36, 5933.

    Article  CAS  Google Scholar 

  3. R. H. Chen, A. M. Buko, D. N. Whitern, J. B. Mcalpine, J. Antibiot. (Tokyo), 1989, 42, 512.

    Article  CAS  Google Scholar 

  4. T. Temal, H. Jary, M. Auberval, S. Lively, D. Guédin, J. Vevert, P. Deprez, Bioorg. Med. Chem. Lett., 2013, 23, 2455.

    Article  CAS  PubMed  Google Scholar 

  5. P. Deprez, T. Temal, H. Jary, M. Auberval, S. Lively, D. Guédin, Bioorg. Med. Chem. Lett., 2013, 23, 2455.

    Article  CAS  PubMed  Google Scholar 

  6. P. M. Wehn, P. E. Harrington, T. J. Carlson, J. Davis, P. Deprez, C. H. Fotsch, M. P. Grillo, J. Y.-L. Lu, S. Morony, K. Pattabiraman, S. F. Poon, J. D. Reagan, D. J. St. Jean, Jr., T. Temal, M. Wang, Y. Yang, C. Henley, S. E. Lively, Bioorg. Med. Chem. Lett., 2013, 23, 6625.

    Article  CAS  PubMed  Google Scholar 

  7. U. R. Mane, D. Mohanakrishnan, D. Sahal, P. R. Murumkar, R. Giridhar, M. Ram, Eur. J. Med. Chem., 2014, 79, 422.

    Article  CAS  PubMed  Google Scholar 

  8. V. G. DeVries, J. D. Bloom, M. D. Dutia, A. S. Katocs, E. E. Largis, J. Med. Chem., 1989, 32, 2318.

    Article  CAS  PubMed  Google Scholar 

  9. S. L. Nowotarski, B. Pachaiyappan, S. L. Holshouser, C. J. Kutz, Y. Li, Y. Huang, S. K. Sharma, R. A. Casero, P. M. Woster, Bioorg. Med. Chem., 2015, 23, 1601.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. A. Esteves-Souza, K. Pissinate, M. D. Graça Nascimento, N. F. Grynberg, A. Echevarria, Bioorg. Med. Chem., 2006, 14, 492.

    Article  CAS  PubMed  Google Scholar 

  11. J. A. Kowalski, A. D. Swinamer, I. Muegge, A. B. Eldrup, A. Kukulka, C. L. Cywin, S. De Lombaert, Bioorg. Med. Chem. Lett., 2010, 20, 3703.

    Article  CAS  PubMed  Google Scholar 

  12. M. Manickam, T. Pillaiyar, P. Boggu, E. Venkateswararao, H. B. Jalani, N.-D. Kim, S. K. Lee, J. S. Jeon, S. K. Kim, S.-H. Jung, Eur. J. Med. Chem., 2016, 117, 113.

    Article  CAS  PubMed  Google Scholar 

  13. M. L. Sanders, I. O. Donkor, Bioorg. Med. Chem. Lett., 2006, 16, 1965.

    Article  CAS  PubMed  Google Scholar 

  14. I. Gallou, Org. Prep. Proced. Int., 2007, 39, 355.

    Article  CAS  Google Scholar 

  15. T. P. Vishnyakova, I. A. Golubeva, E. V. Glebova, Russ. Chem. Rev., 1985, 54, 249.

    Article  Google Scholar 

  16. D. F. Kutepov, Russ. Chem. Rev., 1962, 31, 633.

    Article  Google Scholar 

  17. F. Bigi, R. Maggi, G. Sartori, Green Chem., 2000, 2, 140.

    Article  CAS  Google Scholar 

  18. N. F. Lazareva, B. A. Gostevskii, Russ. Chem. Bull., 2017, 66, 2199.

    Article  CAS  Google Scholar 

  19. A. Nefzi, N. A. Ong, R. A. Houghten. Tetrahedron Lett., 2000, 41, 5441.

    Article  CAS  Google Scholar 

  20. M. Manickam, H. B. Jalani, T. Pillaiyar, N. Sharma, P. R. Boggu, E. Venkateswararao, Y.-J. Lee, E.-S. Jeon, S.-H. Jung, Eur. J. Med. Chem., 2017, 134, 379.

    Article  CAS  PubMed  Google Scholar 

  21. T. Mohy El Dine, S. Chapron, M.-C. Duclos, N. Duguet, F. Popowycz, M. Lemaire, Eur. J. Org. Chem., 2013, 2013, 5445.

    Article  CAS  Google Scholar 

  22. H.-M. Wang, H.-X. Li, X.-Y. Yu, Z.-G. Ren, J.-P. Lang, Tetrahedron, 2011, 67, 1530.

    Article  CAS  Google Scholar 

  23. J. C. Anderson, R. Bou-Moreno, Tetrahedron, 2010, 66, 9182.

    Article  CAS  Google Scholar 

  24. J. C. Anderson, R. B. Moreno, Org. Biomol. Chem., 2012, 10, 1334.

    Article  CAS  PubMed  Google Scholar 

  25. S. R. Jagtap, Y. P. Patil, A. G. Panda, B. M. Bhanage, Synth. Commun., 2009, 39, 2093.

    Article  CAS  Google Scholar 

  26. F. Saliu, B. Rindone, Tetrahedron Lett., 2010, 51, 6301.

    Article  CAS  Google Scholar 

  27. S. Fujita, B. M. Bhanage, M. Arai, Chem. Lett., 2004, 33, 742.

    Article  Google Scholar 

  28. S. Fujita, B. M. Bhanage, H. Kanamaru, M. Arai, J. Mol. Catal. A Chem., 2005, 230, 43.

    Article  CAS  Google Scholar 

  29. R. Ballini, D. Fiorini, R. Maggi, P. Righi, G. Sartori, R. Sartorio, Green Chem., 2003, 5, 396.

    Article  CAS  Google Scholar 

  30. P. A. Duspara, M. S. Islam, A. J. Lough, R. A. Batey, J. Org. Chem., 2012, 77, 10362.

    Article  CAS  PubMed  Google Scholar 

  31. M. Wang, J. Han, X. Si, Y. Hu, J. Zhu, X. Sun, Tetrahedron Lett., 2018, 59, 1614.

    Article  CAS  Google Scholar 

  32. K. Smith, G. El-Hiti, M. Alshammari, Synthesis, 2012, 44, 2013.

    Article  CAS  Google Scholar 

  33. K. Smith, G. A. El-Hiti, M. B. Alshammari, J. Org. Chem., 2012, 77, 11210.

    Article  CAS  PubMed  Google Scholar 

  34. S. H. Kim, S. H. Hong, Org. Lett., 2016, 18, 212.

    Article  CAS  PubMed  Google Scholar 

  35. D. J. Díaz, K.-G. Hylton, L. McElwee-White, J. Org. Chem., 2006, 71, 734.

    Article  CAS  PubMed  Google Scholar 

  36. L. Jin, D. S. Weinberger, M. Melaimi, C. E. Moore, A. L. Rheingold, G. Bertrand, Angew. Chem., Int. Ed., 2014, 53, 9059.

    Article  CAS  Google Scholar 

  37. K. Orito, M. Miyazawa, T. Nakamura, A. Horibata, H. Ushito, H. Nagasaki, M. Yuguchi, S. Yamashita, T. Yamazaki, M. Tokuda, J. Org. Chem., 2006, 71, 5951.

    Article  CAS  PubMed  Google Scholar 

  38. J. H. Park, J. C. Yoon, Y. K. Chung, Adv. Synth. Catal., 2009, 351, 1233.

    Article  CAS  Google Scholar 

  39. S. L. Peterson, S. M. Stucka, C. J. Dinsmore, Org. Lett., 2010, 12, 1340.

    Article  CAS  PubMed  Google Scholar 

  40. D. Chaturvedi, N. Mishra, V. Mishra, Monatsh. Chem. — Chem. Mon., 2008, 139, 267.

    Article  CAS  Google Scholar 

  41. C. Wu, H. Cheng, R. Liu, Q. Wang, Y. Hao, Y. Yu, F. Zhao, Green Chem., 2010, 12, 1811.

    Article  CAS  Google Scholar 

  42. D.-L. Kong, L.-N. He, J.-Q. Wang, Synlett, 2010, 2010, 1276.

    Article  CAS  Google Scholar 

  43. A. V. Bogdanov, L. I. Musin, V. F. Mironov, Arkivoc, 2015, 2015, 362.

    Google Scholar 

  44. D. Yamauchi, T. Nishimura, H. Yorimitsu, Angew. Chem., Int. Ed., 2017, 56, 7200.

    Article  CAS  Google Scholar 

  45. F. Li, C. Sun, H. Shan, X. Zou, J. Xie, ChemCatChem, 2013, 5, 1543.

    Article  CAS  Google Scholar 

  46. S. C. Ghosh, C. C. Li, H. C. Zeng, J. S. Y. Ngiam, A. M. Seayad, A. Chen, Adv. Synth. Catal., 2014, 356, 475.

    Article  CAS  Google Scholar 

  47. Z. Li, Z. Wang, W. Zhu, Y. Xing, Y. Zhao, Synth. Commun., 2005, 35, 2325.

    Article  CAS  Google Scholar 

  48. E. A. Chugunova, N. I. Akylbekov, A. D. Voloshina, N. V. Kulik, V. V. Zobov, V. M. Babaev, N. V. Gavrilov, A. R. Burilov, Synth. Commun., 2016, 46, 1560.

    Article  CAS  Google Scholar 

  49. A. V. Smolobochkin, A. S. Gazizov, A. R. Burilov, M. A. Pudovik, Russ. J. Org. Chem., 2015, 85, 1779.

    CAS  Google Scholar 

  50. A. V. Smolobochkin, A. S. Gazizov, Yu. K. Voronina, A. R. Burilov, M. A. Pudovik, Russ. Chem. Bull., 2016, 65, 731.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    A. V. Smolobochkin, A. S. Gazizov, A. R. Burilov & M. A. Pudovik

Authors
  1. A. V. Smolobochkin
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  2. A. S. Gazizov
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  3. A. R. Burilov
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  4. M. A. Pudovik
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Correspondence to A. V. Smolobochkin.

Additional information

Based on the materials of the V All-Russian Organic Chemistry Conference (ROCC-V) (September 10–14, 2018, Vladikavkaz, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0662–0670, April, 2019.

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Smolobochkin, A.V., Gazizov, A.S., Burilov, A.R. et al. Ureas bearing alkylaromatic moieties: their synthesis and biological activity. Russ Chem Bull 68, 662–670 (2019). https://doi.org/10.1007/s11172-019-2473-8

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  • DOI: https://doi.org/10.1007/s11172-019-2473-8

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