Skip to main content
Log in

New Possibilities of the Kabachnik–Fields and Pudovik Reactions in the Phthalocyanine-Catalyzed Syntheses of α-Aminophosphonic and α-Aminophosphinic Acid Derivatives

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The results of systematic studies demonstrated wide possibilities of the three-component Kabachnik–Fields and two-component Pudovik reactions catalyzed by metal phthalocyanines in the synthesis of structurally diverse α-aminophosphonates. Extension of this catalytic method to the synthesis α-aminophosphinates gave rise to a series of α-amino- and α-hydrazinophosphinates based on biogenic amino acids. A number of α-hydrazinophosphonates showed a good antioxidant activity.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Sheridan, R.P., J. Chem. Inf. Comput. Sci., 2002, vol. 42, p. 103. doi 10.1021/ci0100806

    Article  CAS  PubMed  Google Scholar 

  2. Grembecka, J., Mucha, A., Cierpicki, T., and Kafarski, P., J. Med. Chem., 2003, vol. 46, p. 2641. doi 10.1021/jm030795v

    Article  CAS  PubMed  Google Scholar 

  3. Miziak, P., Zon, J., Amrhein, N., and Gancarz, R., Phytochemistry, 2007, vol. 68, no. 4, p. 407. doi 10.1016/j.phytochem.2006.11.022

    Article  CAS  PubMed  Google Scholar 

  4. Oesapay, G. and Csiba, A., Eur. J. Med. Chem., 1993, vol. 28, no. 5, p. 355. doi 10.1016/0223-5234(93)90122-U

    Article  Google Scholar 

  5. Deborah, A., Malloy, E., Demarest, K., and Jordan, J., Bioorg. Med. Chem., 1996, vol. 4, no. 10, p. 1693. doi 10.1016/0968-0896(96)00186-1

    Article  Google Scholar 

  6. Kafarski, P. and Lejczak, B., Phosphorus, Sulfur Silicon Relat. Elem., 1991, vol. 63, p. 193. doi 10.1080/10426509108029443

    Article  CAS  Google Scholar 

  7. Liu, W., Rogers, C.J., Fisher, A.J., and Toney, M., Biochemistry, 2002, vol. 41, p. 12 320. doi 10.1021/bi026318g

    Google Scholar 

  8. Song, B.A., Wu, Y.L., Yang, S., Hu, D.Y., He, X.Q., and Jin, L.H., Molecules, 2003, vol. 8, no. 1, p. 186. doi 10.3390/80100186

    Article  CAS  PubMed Central  Google Scholar 

  9. Giannousis, P.P. and Bartlett, P.A., J. Med. Chem., 1987, vol. 30, no. 9, p. 1603. doi 10.1021/jm00392a014

    Article  CAS  PubMed  Google Scholar 

  10. Krawczyk, K.H. and Bartczak, T.J., Phosphorus, Sulfur Silicon Relat. Elem., 1993, vol. 82, p. 117. doi 10.1080/10426509308047415

    Article  CAS  Google Scholar 

  11. Cameron, D.G., Hudson, H.R., and Pianka, M., Phosphorus, Sulfur Silicon Relat. Elem., 1993, vol. 83, p. 21. doi 10.1080/10426509308034344

    Article  CAS  Google Scholar 

  12. Yang, S., Gao, X.W., Diao, C.L., Song, B.A., Jin, L.H., Xu, G.F., Zhang, G.P., Wang, W., Hu, D.U., Yue, M., Zhou, X., and Lu, P., Chin. J. Chem., 2006, vol. 24, no. 11, p. 1581. doi 10.1002/cjoc.200690296

    Article  CAS  Google Scholar 

  13. Allen, J.G., Atherton, F.R., Hall, M.J., Hassall, C.H., Holmes, S.W., Lambert, R.W., Nisbet, L.J., and Ringrose, P.S., Nature, 1978, vol. 272, p. 56. doi 10.1038/272056a0

    Article  CAS  PubMed  Google Scholar 

  14. Atherton, F.R., Hall, M.J., Hassall, C.H., Lambert, R.W., Lloyd, W.J., and Ringrose, P.S., Antimicrob. Agents Chemother., 1979, vol. 15, no. 5, p. 677. doi 10.1128/AAC.15.5.684

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Haranath, P., Babu, M.F.S., Anasuyamma, U., Raju, C.N., and Reddy, C.S., Heteroatom Chem., 2005, vol. 16, no. 7, p. 572. doi 10.1002/hc.20154

    Article  CAS  Google Scholar 

  16. Kase, H., Yamato, M., Koguchi, T., Okachi, R., Kasai, M., Shirahata, K., Kawamoto, I., Shuto, K., and Karasawa, A., EP Patent no. 61 172; Chem. Abstr., 1983, vol. 98, no. 107 793 m.

  17. Hirschman, R., Smith, A.B. III, Taylor, C.M., Benkovic, P.A., Taylor, S.D., Yager, K.M., Spengler, P.A., and Venkovic, S.J., Science, 1994, vol. 265, p. 234. doi 10.1126/science.8023141

    Article  Google Scholar 

  18. Moriarty, R.M., Tao, A., and Liu, K., Synth. Commun., 1998, vol. 28, no. 9, p. 1601. doi 10.1080/00397919808006864

    Article  CAS  Google Scholar 

  19. Dzhimbaev, V.Zh., Tukanova, S.K., and Butin, B.M., Biologicheski aktivnye veshchestva (Biologically Active Compounds), Nauka: Alma-Ata, 1989, p. 128.

    Google Scholar 

  20. Kafarski, P. and Lejczak, B., Curr. Med. Chem.: Anti-Cancer Agents, 2001, vol. 1, p. 301. doi 10.2174/1568011013354543

    CAS  PubMed  Google Scholar 

  21. Atherton, F., Hassal, C., and Lambert, R., J. Med. Chem., 1986, vol. 29, p. 29. doi 10.1021/jm00151a005

    Article  CAS  PubMed  Google Scholar 

  22. Allen, M.C., Fuhrer, W., Tuck, B., Wade, R., and Wood, J., J. Med. Chem., 1989, vol. 32, p. 1652. doi 10.1021/jm00127a041

    Article  CAS  PubMed  Google Scholar 

  23. Sasai, H., Arai, S., Tahara, Y., and Shibasaki, M., J. Org. Chem., 1995, vol. 60, p. 6656. doi 10.1021/jo00126a003

    Article  CAS  Google Scholar 

  24. Kabachnik, M.I. and Medved’, T.Ya., Dokl. Akad. Nauk SSSR, 1952, vol. 83, no. 45, p. 689.

    CAS  Google Scholar 

  25. Fields, E.K., J. Am. Chem. Soc., 1952, vol. 74, p. 1528. doi 10.1021/ja01126a054

    Article  CAS  Google Scholar 

  26. Petrov, K.A., Chauzov, V.A., and Erokhina, T.S., Russ. Chem. Rev., 1974, vol. 43, p. 984. doi 10.1070/RC1974v043n11ABEH001877

    Article  Google Scholar 

  27. Kukhar’, V.P. and Solodenko, V.A., Russ. Chem. Rev., 1987, vol. 56, p. 859. doi 10.1070/RC1987v056n09ABEH003310

    Article  Google Scholar 

  28. Cherkasov, R.A. and Galkin, V.I., Russ. Chem. Rev., 1998, vol. 67, no. 10, p. 857. doi 10.1070/RC1998v067n10ABEH000421

    Article  Google Scholar 

  29. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, Kukhar, V.P. and Hudson, H.R., Eds., Chichester: Wiley, 2000.

    Google Scholar 

  30. Zefirov, N.S. and Matveeva, E.D., Arkivoc, 2008, part (i), p. 1. doi 10.3998/ark.5550190.0009.101

    Google Scholar 

  31. Kukhar’, V.P., Svistunova, N.Yu., Solodenko, V.A., and Soloshonok, V.A., Russ. Chem. Rev., 1993, vol. 62, no. 3, p. 261. doi 10.1070/RC1993v062n03ABEH000017

    Article  Google Scholar 

  32. Uziel, J. and Genêt, J.P., Russ. J. Org. Chem., 1997, vol. 33, no. 11, p. 1521.

    CAS  Google Scholar 

  33. Gancarz, R., Tetrahedron, 1995, vol. 51, p. 10 627. doi 10.1016/0040-4020(95)00634-K

    Article  Google Scholar 

  34. Zefirov, N.S., Matveeva, E.D., and Shuvalov, M.V., Sci. Synth. Multicomp. React., 2013, vol. 1, p. 273.

    Google Scholar 

  35. Pudovik, A.N., Dokl. Akad. Nauk SSSR, 1952, vol. 83, p. 865.

    CAS  Google Scholar 

  36. Matveeva, E.D., Shuvalov, M.V., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2011, vol. 60, no. 2, p. 242. doi 10.1007/s11172-011-0040-z

    Article  CAS  Google Scholar 

  37. Matveeva, E.D., Shuvalov, M.V., Podrugina, T.A., Proskurnina, M.V., and Zefirov, N.S., Phosphorus, Sulfur Silicon Relat. Elem., 2015, vol. 190, no. 2, p. 220. doi 10.1080/10426507. 2014.914936

    Article  CAS  Google Scholar 

  38. Matveeva, E.D., Podrugina, T.A., Prisyajnoy, M.V., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2006, vol. 55, no. 7, p. 1209. doi 10.1007/s11172-006-0400-2

    Article  CAS  Google Scholar 

  39. Matveeva, E.D., Podrugina, T.A., Tishkovskaya, E.V., Tomilova, L.G., and Zefirov, N.S., Synlett, 2003, no. 15, p. 2321. doi 10.1055/s-2003-42118

    Article  CAS  Google Scholar 

  40. Matveeva, E.D., Podrugina, T.A., Borisenko, A.A., Kolesnikova, I.N., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2009, vol. 58, no. 1, p. 119. doi 10.1007/s11172-009-0018-2

    Article  CAS  Google Scholar 

  41. Matveeva, E.D. and Zefirov, N.S., Russ. J. Org. Chem., 2006, vol. 42, no. 8, p. 1237. doi 10.1134/S1070428006080240

    Article  CAS  Google Scholar 

  42. Matveeva, E.D., Podrugina, T.A., Prisyazhnoi, M.V., and Zefirov, N.S., Moscow Univ. Chem. Bull., 2007, vol. 62, no. 5, p. 273. doi 10.3103/S0027131407050124

    Article  Google Scholar 

  43. Matveeva, E.D., Podrugina, T.A., Prisyazhnoi, M.V., Rusetskaya, I.N., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2007, vol. 56, no. 4, p. 798. doi 10.1007/s11172-007-0119-8

    Article  CAS  Google Scholar 

  44. Matveeva, E.D., Podrugina, T.A., Prisyazhnoi, M.V., Bachurin, S.O., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, no. 1, p. 200. doi 10.1007/s11172-010-0063-x

    Article  CAS  Google Scholar 

  45. Khairullin, V.K., Pudovik, M.A., Shagidullin, R.R., Mukhamadeeva, R.M., Shakirov, I.Kh., and Pudovik, A.N., Russ. J. Gen. Chem., 1994, vol. 64, no. 4, p. 557.

    Google Scholar 

  46. Gryaznov, P.I., Kurochkina, S.N., Musin, R.Z., Pudovik, A.N., and Kibardin, A.M., Russ. J. Gen. Chem., 1996, vol. 66, no. 3, p. 372.

    Google Scholar 

  47. Nifant’ev, E.E., Zyk, N.V., and Koroteev, M.P., Zh. Obshch. Khim., 1975, vol. 45, no. 5, p. 1455.

    Google Scholar 

  48. Matveeva, E.D., Podrugina, T.A., Kolesnikova, I.N., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, no. 2, p. 411. doi 10.1007/s11172-010-0094-3

    Article  CAS  Google Scholar 

  49. Matveeva, E.D., Podrugina, T.A., Kolesnikova, I.N., Prisyazhnoi, M.V., Karateev, G.G., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, no. 2, p. 418. doi 10.1007/s11172-010-0095-2

    Article  CAS  Google Scholar 

  50. Matveeva, E.D., Podrugina, T.A., Kolesnikova, I.N., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, no. 3, p. 584. doi 10.1007/s11172-010-0114-3

    Article  CAS  Google Scholar 

  51. Matveeva, E.D., Kolesnikova, I.N., and Zefirov, N.S., Russ. Chem. Bull., Int. Ed., 2011, vol. 60, no. 2, p. 248. doi 10.1007/s11172-011-0041-y

    Article  CAS  Google Scholar 

  52. Davis, F.A., Lee, S., Zhang, H., and Fanelli, D.L., J. Org. Chem., 2000, vol. 65, p. 8704. doi 10.1021/jo001179z

    Article  CAS  PubMed  Google Scholar 

  53. Burgess, K., Ho, K.K., and Pettitt, B.M., J. Am. Chem. Soc., 1994, vol. 116, p. 799. doi 10.1021/ja00081a063

    Article  CAS  Google Scholar 

  54. Walsh, J.J., Metzler, D.E., Powell, D., and Jacobson, R.A., J. Am. Chem. Soc., 1980, vol. 102, p. 7136. doi 10.1021/ja00543a058

    Article  CAS  Google Scholar 

  55. Ballatore, C., McGuigan, C., De Clercq, E., and Balzarini, J., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 1053. doi 10.1016/S0960-894X(01)00128-7

    Article  CAS  PubMed  Google Scholar 

  56. Kaboudin, B., Haruki, T., Yamagishi, T., and Yokomatsu, T., Tetrahedron, 2007, vol. 63, p. 8199. doi 10.1016/j.tet.2007.05.118

    Article  CAS  Google Scholar 

  57. Diel, P.J. and Maier, L., Phosphorus, Sulfur Silicon Relat. Elem., 1988, vol. 36, p. 85. doi 10.1080/03086648808079002

    Article  CAS  Google Scholar 

  58. Gandhi, S. and Abramov, A.Y., Oxid. Med. Cell. Longevity, 2012, article ID 428 010. doi 10.1155/2012/428010

    Google Scholar 

  59. Kim, G.H., Kim, J.E., Rhie, S.J., and Yoon, S., Exp. Neurobiol., 2015, vol. 24, p. 325. doi 10.5607/en.2015.24.4.325

    Article  PubMed  PubMed Central  Google Scholar 

  60. Halliwel, B., Plant Physiol., 2006, vol. 141, p. 312. doi 10.1104/pp.106.077073

    Article  CAS  Google Scholar 

  61. Firuzi, O., Miri, R., Tavakkoli, M., and Saso, L., Curr. Med. Chem., 2011, vol. 18, p. 3871. doi 10.2174/092986711803414368

    Article  CAS  PubMed  Google Scholar 

  62. Murphy, M.P., Free Radicals Biol. Med., 2014, vol. 66, p. 20. doi 10.1016/j.freeradbiomed.2013.04.010

    Article  CAS  Google Scholar 

  63. Kelsey, N.A., Wilkins, H.M., and Linseman, D.A., Molecules, 2010, vol. 15, p. 7792. doi 10.3390/molecules15117792

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  64. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., and Rice-Evans, C., Free Radicals Biol. Med., 1999, vol. 26, nos. 9–10, p. 1231. doi 10.1016/S0891-5849(98)00315-3

  65. Benzie, I.F. and Strain, J.J., Anal. Biochem., 1996, vol. 239, no. 1, p. 70. doi 10.1006/abio.1996.0292

    Article  CAS  PubMed  Google Scholar 

  66. Benzie, I.F. and Strain, J.J., Methods Enzymol., 1999, vol. 299, p.15. doi 10.1016/S0076-6879(99)99005-5

  67. Meir, S., Kanner, J., Akiri, B., and Philosoph-Hadas, S., J. Agric. Food Chem., 1995, vol. 43, p. 1813. doi 10.1021/jf00055a012

    Article  CAS  Google Scholar 

  68. Loo, A.Y., Jain, K., and Darah, I., Food Chem., 2007, vol. 104, no. 1, p. 300. doi 10.1016/j.foodchem.2006.11.048

    Article  CAS  Google Scholar 

  69. Prior, R.L., Wu, X.L., and Schaich, K., J. Agric. Food Chem., 2005, vol. 53, p. 4290. doi 10.1021/jf0502698

    Article  CAS  PubMed  Google Scholar 

  70. Gulcin, I., Arch. Toxicol., 2012, vol. 86, p. 345. doi 10.1007/s00204-011-0774-2

    Article  CAS  PubMed  Google Scholar 

  71. Bravo-Altamirano, K., Huang, Z., and Montchamp, J.L., Tetrahedron, 2005, vol. 61, p. 6315. doi 10.1016/j.tet.2005.03.107

    Article  CAS  Google Scholar 

  72. Borg, S., Estenne-Bouhtou, G., Luthman, K., Csoeregh, I., Hesselink, W., and Hacksell, U., J. Org. Chem., 1995, vol. 60, no. 10, p. 3112. doi 10.1021/jo00115a029

    Article  CAS  Google Scholar 

  73. Von Hartmut, N. and Oehme, C., J. Prakt. Chem., 1972, vol. 314, p. 759. doi 10.1002/prac.19723140508

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to T. A. Podrugina.

Additional information

Dedicated to the 110th anniversary of M.I. Kabachnik’s birth

Original Russian Text © M.V. Shuvalov, S.Yu. Maklakova, E.V. Rudakova, N.V. Kovaleva, G.F. Makhaeva, T.A. Podrugina, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1410–1425.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shuvalov, M.V., Maklakova, S.Y., Rudakova, E.V. et al. New Possibilities of the Kabachnik–Fields and Pudovik Reactions in the Phthalocyanine-Catalyzed Syntheses of α-Aminophosphonic and α-Aminophosphinic Acid Derivatives. Russ J Gen Chem 88, 1761–1775 (2018). https://doi.org/10.1134/S1070363218090013

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218090013

Keywords

Navigation