Skip to main content

Advertisement

SpringerLink
Log in

Azidoisocyanides, New Bifunctional Reagents for Multicomponent Reactions and Biomolecule Modifications

  • Published:
Chemistry of Natural Compounds Aims and scope

The synthetic capabilities of chiral α,β-azidoisocyanides were systematically reviewed. The potential of using them as bifunctional building blocks for multicomponent Passerini and Ugi reactions and also for Cu(I)-catalyzed [3+2]-cycloaddition to form 1,2,3-triazoles was demonstrated. The bifunctional nature of these compounds enabled the development of a methodology for preparing peptides containing an azide group and conjugating them subsequently with various biologically active compounds containing an ethynyl group for targeted modification of biomolecules.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  1. A. Domling and I. Ugi, Angew. Chem., Int. Ed., 39, 3168 (2000).

    Article  CAS  Google Scholar 

  2. A. Domling, Chem. Rev., 106, 17 (2006).

    Article  PubMed  Google Scholar 

  3. M. Passerini and L. Simone, Gazz. Chim. Ital., 51, 126 (1921).

    CAS  Google Scholar 

  4. L. Banfi and R. Riva, The Passerini Reaction, in: Organic Reactions, A. B. Chapatte (ed.), Wiley, New York, 2005, Vol. 65, 1.

  5. A. V. Gulevich, I. V. Shpilevaya, and V. G. Nenajdenko, Eur. J. Org. Chem., 3801 (2009).

  6. I. Ugi, R. Meyr, U. Fetzer, and C. Steinbruckner, Angew. Chem., 71, 386 (1959).

    Google Scholar 

  7. I. Ugi and C. Steinbruckner, Angew. Chem., 72, 267 (1960).

    Article  CAS  Google Scholar 

  8. A. V. Gulevich, A. G. Zhdanko, R. V. A. Orru, and V. G. Nenajdenko, Chem. Rev., 110, 5235 (2010).

    Article  CAS  PubMed  Google Scholar 

  9. V. G. Nenajdenko (ed.), Isocyanide Chemistry: Application in Synthesis and Materials Science, Wiley-VCH, Weinheim, Germany, 2012.

    Google Scholar 

  10. A. V. Gulevich, N. E. Shevchenko, E. S. Balenkova, G.-V. Roschenthaler, and V. G. Nenajdenko, Synlett, 403 (2009).

  11. A. G. Zhdanko and V. G. Nenajdenko, J. Org. Chem., 74, 884 (2009).

    Article  CAS  PubMed  Google Scholar 

  12. V. G. Nenajdenko, A. V. Gulevich, and E. S. Balenkova, Tetrahedron, 62, 5922 (2006).

    Article  CAS  Google Scholar 

  13. A. V. Gulevich, E. S. Balenkova, and V. G. Nenajdenko, J. Org. Chem., 72, 7878 (2007).

    Article  CAS  PubMed  Google Scholar 

  14. A. V. Gulevich, N. E. Shevchenko, E. S. Balenkova, G.-V. Roschenthler, and V. G. Nenajdenko, Tetrahedron, 64, 11706 (2008).

    Article  CAS  Google Scholar 

  15. A. G. Zhdanko, A. V. Gulevich, and V. G. Nenajdenko, Tetrahedron, 65, 4692 (2009).

    Article  CAS  Google Scholar 

  16. V. G. Nenajdenko, A. V. Gulevich, K. Yu. Chernichenko, N. V. Sokolova, and E. S. Balenkova, Mendeleev Commun., 21, 245 (2011).

    Article  CAS  Google Scholar 

  17. A. V. Gulevich, L. S. Koroleva, O. V. Morozova, V. N. Bakhvalova, V. N. Silnikov, and V. G. Nenajdenko, Beilstein J. Org. Chem., 7, 1135 (2011).

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  18. A. Domling, W. Wang, and K. Wang, Chem. Rev., 112, 3083 (2012).

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  19. M. M. Staveski and S. F. Sneddon, Alpha Acyloxyacetamides for Kallikrein and Urokinase Inhibition, WO 2003101941, May 28, 2003.

  20. N. A. M. Yehia, W. Antuch, B. Beck, S. Hess, V. Schauer-Vukasinovic, M. Almstetter, P. Furer, E. Herdtweck, and A. Domling, Bioorg. Med. Chem. Lett., 14, 3121 (2004).

    Article  CAS  PubMed  Google Scholar 

  21. M. Nakamura, M. Yamaguchi, O. Sakai, and J. Inoue, Bioorg. Med. Chem. Lett., 11, 1371 (2003).

    Article  CAS  Google Scholar 

  22. K. Rossen, P. J. Pye, L. M. DiMichele, R. P. Volante, and P. J. Reider, Tetrahedron Lett., 39, 6823 (1998).

    Article  CAS  Google Scholar 

  23. K. Rikimaru, K. Mori, T. Kan, and T. Fukuyama, Chem. Commun., 394 (2005).

  24. A. Suda, A. Ohta, M. Sudoh, T. Tsukuda, and N. Shimma, Heterocycles, 55, 1023 (2001).

    Article  CAS  Google Scholar 

  25. A. Doemling, Toluenesulphonylmethyl isocyanide (TOSMIC) and the van Leusen MCR, Org. Chem. Highlights, May 05, 2005.

  26. V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, Angew. Chem., Int. Ed., 41, 2596 (2002).

    Article  CAS  Google Scholar 

  27. C. W. Tornoe, C. Christensen, and M. Meldal, J. Org. Chem., 67, 3057 (2002).

    Article  CAS  PubMed  Google Scholar 

  28. P. Thirumurugan, D. Matosiuk, and K. Jozwiak, Chem. Rev., 113, 4905 (2013).

    Article  CAS  PubMed  Google Scholar 

  29. A. D. Moorhouse and J. E. Moses, ChemMedChem., 3, 715 (2008).

    Article  CAS  PubMed  Google Scholar 

  30. S. G. Agalave, S. R. Maujan, and V. S. Pore, Chem. - Asian J., 6, 2696 (2011).

    Article  CAS  PubMed  Google Scholar 

  31. G. C. Tron, T. P. Pirali, R. A. Billington, P. L. Canonico, G. Sorba, and A. A. Genazzani, Med. Res. Rev., 28, 278 (2008).

    Article  CAS  PubMed  Google Scholar 

  32. H. C. Kolb and K. B. Sharpless, Drug Discovery Today, 8, 1128 (2003).

    Article  CAS  PubMed  Google Scholar 

  33. W. S. Horne, M. K. Yadav, C. D. Stout, and M. R. Ghadiri, J. Am. Chem. Soc., 126, 15366 (2004).

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  34. V. D. Bock, H. Hiemstra, and J. H. van Maarseveen, Eur. J. Org. Chem., 51 (2006).

  35. D. K. Dalvie, A. S. Kalgutkar, S. C. Khojasteh-Bakht, R. S. Obach, and J. P. O’Donnell, Chem. Res. Toxicol., 15, 269 (2002).

    Article  CAS  PubMed  Google Scholar 

  36. J. E. Moses and A. D. Moorhouse, Chem. Soc. Rev., 36, 1249 (2007).

    Article  CAS  PubMed  Google Scholar 

  37. C. O. Kappe and E. V. Eycken, Chem. Soc. Rev., 39, 1280 (2010).

    Article  CAS  PubMed  Google Scholar 

  38. M. Colombo and A. Bianchi, Molecules, 15, 178 (2010).

    Article  CAS  PubMed  Google Scholar 

  39. A. Dondoni, Chem. - Asian J., 2, 700 (2007).

    Article  CAS  PubMed  Google Scholar 

  40. Y. L. Angell and K. Burgess, Chem. Soc. Rev., 36, 1674 (2007).

    Article  CAS  PubMed  Google Scholar 

  41. J. Chen, Z. Nikolovska-Coleska, C.-Y. Yang, C. Gomez, W. Gao, K. Krajewski, S. Jiang, P. Roller, and S. Wang, Bioorg. Med. Chem. Lett., 17, 3939 (2007).

    Article  CAS  PubMed  Google Scholar 

  42. A. E. Cohrt, J. F. Jensen, and T. E. Nielsen, Org. Lett., 12, 5414 (2010).

    Article  CAS  PubMed  Google Scholar 

  43. M. Weiwer, C.-C. Chen, M. M. Kemp, and R. J. Linhardt, Eur. J. Org. Chem., 2611 (2009).

  44. M. Whiting, J. C. Tripp, Y.-C. Lin, W. Lindstrom, A. J. Olson, J. H. Elder, K. B. Sharpless, and V. V. Fokin, J. Med. Chem.,49, 7697 (2006).

    Article  CAS  PubMed  Google Scholar 

  45. V. S. Pore, N. G. Aher, M. Kumar, and P. K. Shukla, Tetrahedron, 62, 11178 (2006).

    Article  CAS  Google Scholar 

  46. F. E. Hahn, V. Langenhahn, and T. Pape, Chem. Commun., 43, 5390 (2005).

    Article  Google Scholar 

  47. A. Flores-Figueroa, O. Kaufhold, K.-O. Feldmann, and F. E. Hahn, Dalton Trans., 9334 (2009).

  48. V. G. Nenajdenko, A. V. Gulevich, N. V. Sokolova, A. V. Mironov, and E. S. Balenkova, Eur. J. Org. Chem., 1445 (2010).

  49. N. V. Sokolova, G. V. Latyshev, N. V. Lukashev, and V. G. Nenajdenko, Org. Biomol. Chem., 4921 (2011).

  50. A. I. Govdi, S. F. Vasilevsky, V. G. Nenajdenko, N. V. Sokolova, and G. A. Tolstikov, Russ. Chem. Bull., 60, 2401 (2011).

    Article  CAS  Google Scholar 

  51. D. V. Vorobyeva, N. V. Sokolova, V. G. Nenajdenko, A. S. Peregudov, and S. N. Osipov, Tetrahedron, 68, 872 (2012).

    Article  CAS  Google Scholar 

  52. A. I. Govdi, S. F. Vasilevsky, N. V. Sokolova, I. V. Sorokina, T. G. Tolstikova, and V. G. Nenajdenko, Mendeleev Commun., 23, 260 (2013).

    Article  CAS  Google Scholar 

  53. N. V. Sokolova, V. G. Nenajdenko, V. B. Sokolov, D. V. Vinogradova, E. F. Shevtsova, L. G. Dubova, and S. O. Bachurin, Beilstein J. Org. Chem., 10, 155 (2014).

    Article  PubMed Central  PubMed  Google Scholar 

  54. G. A. Bowmaker, J. V. Hanna, F. E. Hahn, A. S. Lipton, C. E. Oldham, B. W. Skelton, M. E. Smith, and A. H. White, Dalton Trans., 1710 (2008).

  55. S. Cenini, E. Gallo, A. Caselli, F. Ragaini, S. Fantauzzi, and C. Piangiolio, Coord. Chem. Rev., 250, 1234 (2006).

    Article  CAS  Google Scholar 

  56. M. Meldal and C. W. Tornoe, Chem. Rev., 108, 2952 (2008).

    Article  CAS  PubMed  Google Scholar 

  57. J. A. Dunn and P. L. Pauson, J. Organomet. Chem., 419, 383 (1991).

    Article  CAS  Google Scholar 

  58. N. V. Sokolova and V. G. Nenajdenko, Chem. Heterocycl. Compd., 48, 903 (2012).

    Article  CAS  Google Scholar 

  59. Nonappa and U. Maitra, Org. Biomol. Chem., 6, 657 (2008).

    Article  CAS  PubMed  Google Scholar 

  60. E. Virtanen and E. Kolehmainen, Eur. J. Org. Chem., 3385 (2004).

  61. Y. Li and J. R. Dias, Chem. Rev., 97, 283 (1997).

    Article  CAS  PubMed  Google Scholar 

  62. P. Walliman, T. Marti, A. Furer, and F. Diederich, Chem. Rev., 97, 1567 (1997).

    Article  Google Scholar 

  63. E. Sievanen, Molecules, 12, 1859 (2007).

    Article  CAS  PubMed  Google Scholar 

  64. P. W. Swaan, K. M. Hillgren, F. C. Szoka, and J. S. Øie, Bioconjugate Chem., 8, 520 (1997).

    Article  CAS  Google Scholar 

  65. E. Petzinger, A. Wickboldt, P. Pagels, D. Starke, and W. Kramer, Hepatology, 30, 1257 (1999).

    Article  CAS  PubMed  Google Scholar 

  66. W. Kramer, G. Wess, G. Schubert, M. Bickel, F. Girbig, U. Gutjahr, S. Kowalewski, K.-H. Baringhaus, A. Enhsen, H. Glombik, S. Mullner, G. Neckermann, S. Schulz, and E. Petzinger, J. Biol. Chem., 267, 18598 (1992).

    CAS  PubMed  Google Scholar 

  67. G. Wess, W. Kramer, G. Schubert, A. Enhsen, K.-H. Baringhaus, H. Glombik, S. Mullner, K. Bock, H. Kleine, M. John, O. Neckermann, and A. Hoffmann, Tetrahedron Lett., 34, 819 (1993).

    Article  CAS  Google Scholar 

  68. S. N. Bavikar, D. B. Salunke, B. G. Hazra, V. S. Pore, R. H. Dodd, J. Thierry, F. Shirazi, M. V. Deshpande, S. Kadreppa, and S. Chattopadhyay, Bioorg. Med. Chem. Lett., 18, 5512 (2008).

    Article  CAS  PubMed  Google Scholar 

  69. D. G. Rivera and L. A. Wessjohann, Molecules, 12, 1890 (2007).

    Article  CAS  PubMed  Google Scholar 

  70. P. Dzubak, M. Hajduch, D. Vydra, A. Hustova, M. Kvasnica, D. Biedermann, L. Markova, M. Urban, and J. Sarek, Nat. Prod. Rep., 23, 394 (2006).

    Article  CAS  PubMed  Google Scholar 

  71. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, and O. B. Flekhter, Bioorg. Khim., 32, 291 (2006).

    CAS  PubMed  Google Scholar 

  72. R. H. Cichewicz and S. A. Kouzi, Med. Res. Rev., 24, 90 (2004).

    Article  CAS  PubMed  Google Scholar 

  73. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, and O. B. Flekhter, Russ. J. Bioorg. Chem., 32, 261 (2006).

    Article  CAS  Google Scholar 

  74. M. G. Moghaddam, F. B. H. Ahmad, and A. Samzadeh-Kermani, Pharmacol. Pharm., 3, 119 (2012).

    Article  CAS  Google Scholar 

  75. C. Jackel and B. Koksch, Eur. J. Org. Chem., 4483 (2005).

  76. K. Burger and W. Hollweck, Synlett, 751 (1994).

  77. W. Hollweck and K. Burger, J. Prakt. Chem., 337, 391 (1995).

    Article  CAS  Google Scholar 

  78. G. T. Shchetnikov, A. S. Peregudov, and S. N. Osipov, Synlett, 136 (2007).

  79. G. T. Shchetnikov, M. A. Zotova, C. Bruneua, P. H. Dixneuf, and S. N. Osipov, Eur. J. Org. Chem., 1587 (2010).

  80. D. V. Vorobyeva, N. M. Karimova, T. P. Vasilyeva, S. N. Osipov, G. T. Shchetnikov, I. L. Odinets, and G.-V. Roschenthaler, J. Fluorine Chem., 131, 378 (2010).

    Article  CAS  Google Scholar 

  81. R. Suzuki, H. Tsukuda, N. Watanabe, Y. Kuwatani, and I. Ueda, Tetrahedron, 54, 2477 (1998).

    Article  CAS  Google Scholar 

  82. N. Sewald and K. Burger, Z. Naturforsch. B: Chem. Sci., 45, 871 (1990).

    CAS  Google Scholar 

  83. A. S. Golubev, N. N. Sergeeva, L. Hennig, A. F. Kolomiets, and K. Burger, Tetrahedron, 59, 1389 (2003).

    Article  CAS  Google Scholar 

  84. N. V. Sokolova, D. V. Vorobyeva, S. N. Osipov, T. P. Vasilyeva, and V. G. Nenajdenko, Synthesis, 130 (2012).

  85. L. B. Josefsen and R. W. Boyle, Met.-Based Drugs, 1 (2008).

  86. J.-P. Taquet, C. Frochot, V. Manneville, and M. Barberi-Heyob, Curr. Med. Chem., 14, 1673 (2007).

    Article  CAS  PubMed  Google Scholar 

  87. H. J. Berthold, T. Schotten, F. Hoffmann, and J. Thiem, Synthesis, 741 (2010).

  88. H. J. Berthold, S. Franke, J. Thiem, and T. Schotten, J. Org. Chem., 75, 3859 (2010).

    Article  CAS  PubMed  Google Scholar 

  89. N. V. Sokolova, T. Schotten, H. J. Berthold, J. Theim, and V. G. Nenajdenko, Synthesis, 556 (2013).

  90. M. Sienczyk and J. Oleksyszyn, Curr. Med. Chem., 16, 1673 (2009).

    Article  CAS  PubMed  Google Scholar 

  91. G. F. Makhaeva, A. Y. Aksinenko, V. B. Sokolov, O. G. Serebryakova, and R. J. Richardson, Bioorg. Med. Chem. Lett., 19, 5528 (2009).

    Article  CAS  PubMed  Google Scholar 

  92. N. V. Sokolova, V. G. Nenajdenko, V. B. Sokolov, O. G. Serebryakova, and G. F. Makhaeva, Bioorg. Med. Chem. Lett., 21, 7216 (2011).

    Article  CAS  PubMed  Google Scholar 

  93. A. Saxena, A. M. G. Redman, X. Jiang, O. Lockridge, and B. P. Doctor, Biochemistry, 36, 14642 (1997).

    Article  CAS  PubMed  Google Scholar 

  94. S. O. Bachurin, E. P. Shevtsova, N. N. Lermontova, T. P. Serkova, and R. R. Ramsay, NeuroToxicology, 17, 897 (1996).

    CAS  PubMed  Google Scholar 

  95. A. B. Knott, G. Perkins, R. Schwarzenbacher, and E. Bossy-Wetzel, Nat. Rev. Neurosci., 9, 505 (2008).

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  96. J. Lee, J. H. Boo, and H. Ryu, Adv. Drug Delivery Rev., 61, 1316 (2009).

    Article  CAS  Google Scholar 

  97. S. O. Bachurin, Vopr. Med. Khim., 47, 155 (2001).

    CAS  PubMed  Google Scholar 

  98. G. P. Eckert, K. Renner, S. H. Eckert, J. Eckmann, S. Hagl, R. M. Abdel-Kader, C. Kurz, K. Leuner, and W. E. Muller, Mol. Neurobiol., 46, 136 (2012).

    Article  CAS  PubMed  Google Scholar 

  99. S. Zhang, L. Hedskog, C. A. Petersen, B. Winblad, and M. Ankarcrona, J. Alzheimer’s Dis., 21, 389 (2010).

    Google Scholar 

  100. S. H. Eckert, J. Eckmann, K. Renner, G. P. Eckert, K. Leuner, and W. E. Muller, J. Alzheimer’s Dis., 31, 21 (2012).

    CAS  Google Scholar 

Download references

Acknowledgment

The work was supported by the RFBR (Grant 12-03000292-a).

Author information

Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, Leninskie Gory, 1, Bldg. 3, GSP-1, Moscow, 119991, Russian Federation

    N. V. Sokolova & V. G. Nenajdenko

  2. A. N. Nesmeyanov Institute of Elementorganic Compounds, Russian Academy of Sciences, 119991, GSP-1, Moscow, B-334, Ul. Vavilova, 28., Russia

    V. G. Nenajdenko

Authors
  1. N. V. Sokolova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. G. Nenajdenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. G. Nenajdenko.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2014, pp. 177–192.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sokolova, N.V., Nenajdenko, V.G. Azidoisocyanides, New Bifunctional Reagents for Multicomponent Reactions and Biomolecule Modifications. Chem Nat Compd 50, 197–213 (2014). https://doi.org/10.1007/s10600-014-0914-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-014-0914-z

Keywords

Search

Navigation