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Synthesis and properties of 4-phosphorylated derivatives of 5-hydroxyalkylamino-1,3-oxazoles

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Abstract

Reactions of derivatives of diethyl 1-acylamino-2,2,2-trichloroethylphosphonates with different pharmacophore aminoalkanols afforded new 5-hydroxyalkylamino-1,3-oxazole derivatives. The latter are promising substrates for producing new 4-phosphorylated peptidomimetics containing alcohol residues.

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References

  1. Henkel, T. and Zeeck, A., Lieb. Ann. Chem., 1991, p. 367. DOI: 10.1002/jlac.199119910164.

    Google Scholar 

  2. Shiomi, K., Arai, N., Shinose, M., Takahashi, Y., Yoshida, H., Iwabuchi, J., Tanaka, Y., and Omura, S., J. Antibiot., 1995, vol. 48, p. 714. DOI: 10.7164/antibiotics.48.714.

    Article  CAS  Google Scholar 

  3. Iwasaki, S., Namikoshi, M., Kobayashi, H., Furukawa, J., and Okuda, S., Chem. Pharm. Bull., 1986, vol. 34, no. 3, p. 1387. DOI: 10.1248/cpb.34.1387.

    Article  CAS  Google Scholar 

  4. Brazhnikova, M.G., Kudinova, M.K., Potapova, N.P., Filippova, T.M., Borovskii, E., Zelinskii, Ya., and Golik, Yu., Bioorg. Khim., 1976, vol. 2, p. 149.

    CAS  Google Scholar 

  5. Chamberlin, J.W. and Chen, S., J. Antibiot., 1977, vol. 30, no. 3, p. 197. DOI: 10.7164/antibiotics.30.197.

    Article  CAS  Google Scholar 

  6. Delpierre, G.R., Eastwood, F.W., Gream, G.E., Kingston, D.G.I., Sarin, P.S., Todd Lord, A.R., and Williams, D.H., J. Chem. Soc. (C), 1966, p. 1653. DOI: 10.1039/J39660001653.

    Google Scholar 

  7. Carmeli, S., Moore, R.E., Patterson, G.M.L., Corbett, T.H., and Valeriote, F.A., J. Am. Chem. Soc., 1990, vol. 112, no. 22, p. 8195. DOI: 10.1021/ja00178a070.

    Article  CAS  Google Scholar 

  8. Jansen, R., Kunze, B., Reichenbach, H., Jurkiewicz, E., Hunsmann, G., and Hofle, G., Lieb. Ann. Chem., 1992, p. 357. DOI: 10.1002/jlac.199219920163.

    Google Scholar 

  9. Ichiba, T., Yoshida, W.Y., Scheuer, P.J., Higa, T., and Gravalos, D.G., J. Am. Chem. Soc., 1991, vol. 113, no. 8, p. 3173. DOI: 10.1021/ja00008a056.

    Article  CAS  Google Scholar 

  10. Kato, Y., Fusetani, N., Matsunaga, S., Hashimoto, K., Fujita, S., and Furuya, T., J. Am. Chem. Soc., 1986, vol. 108, no. 10, p. 2780. DOI: 10.1021/ja00270a061.

    Article  CAS  Google Scholar 

  11. Kato, Y., Fusetani, N., Matsunaga, S., Hashimoto, K., and Koseki, K., J. Org. Chem., 1988, vol. 53, no. 17, p. 3930. DOI: 10.1021/jo00252a009.

    Article  CAS  Google Scholar 

  12. Brown, K., Cavalla, J.F., Green, D., and Wilson, A.B., Nature, 1968, vol. 219, p. 164. DOI: 10.1038/219164a0.

    Article  CAS  Google Scholar 

  13. Kotani, E., Kobayashi, S., Adrachi, M., Tsujioka, T., Nakamura, K., and Tobinaga, S., Chem. Pharm. Bull., 1989, vol. 37, no. 3, p. 606. DOI: 10.1248/cpb.37.606.

    Article  CAS  Google Scholar 

  14. Yoshida, F. and Topliss, J.G., J. Med. Chem., 2000, vol. 43, no. 13, p. 2575. DOI: 10.1021/jm0000564.

    Article  CAS  Google Scholar 

  15. Seidler, J., McGovern, S.L., Doman, T.N., and Shoichet, B.K., J. Med. Chem., 2003, vol. 46, no. 21, p. 4477. DOI: 10.1021/jm030191r.

    Article  CAS  Google Scholar 

  16. Smith, R.A., Barbosa, J., Blum, C.L., Bobko, M.A., Caringal, Y.V., Dally, R., Johnson, J.S., Katz, M.E., Kennure, N., Lee, W., Lowinger, T.B., Lyons, J., Marsh, V., Rogers, D.H., Swartz, S., Walling, T., and Wild, H., Bio. Med. Chem. Lett., 2001, vol. 11, no. 20, p. 2775. DOI: 10.1016/S0960-894X(01)00571-6.

    Article  CAS  Google Scholar 

  17. Brown, P., Davies, D.T., O'Hanlo, P.J., and Wilson, J.M., J. Med. Chem., 1996, vol. 39, no. 2, p. 446. DOI: 10.1021/jm9503862.

    Article  CAS  Google Scholar 

  18. Bauer, U., Gustafsson, L., Saxin, M., and Svensson, T., WO Patent 073296, 2007.

    Google Scholar 

  19. Morwick, T., Berry, A., Brickwood, J., Cardozo, M., Catron, K., DeTuri, M., Emeigh, J., Homon, C., Hrapchak, M., Jacober, S., Jakes, S., Kaplita, P., Ksiazek, J., Liuzzi, M., Magolda, R., Mao, C., Marshall, D., McNeil, D., Prokopowicz, A., Sarko, C., Scouten, E., Sledziona, C., Sun, S., Watrous, J., Ping Wu, J., and Cywin, C.L., J. Med. Chem., 2006, vol. 49, no. 10, p. 2898. DOI: 10.1021/jm0510979.

    Article  CAS  Google Scholar 

  20. Katritch, V., Jaakola, V.P., Kufareva, I., Lane, J.R., Lin, J., Jzerman, A.P., Yeager, M., Stevens, R.C., and Abagyan, R., J. Med. Chem., 2010, vol. 53, no. 4, p. 1799. DOI: 10.1021/jm901647p.

    Article  CAS  Google Scholar 

  21. Reader, J.C., Ellard, J.M., Boffey, H., Taylor, S., Carr, A.D., Cherry, M., Wilson, M., and Owoare, R.B., WO Patent 139161, 2008.

    Google Scholar 

  22. Nolt, M.B., Smiley, M.A., Varga, S.L., McClain, R.T., Wolkenberg, S.E., and Lindsley, C.W., Tetrahedron, 2006, vol. 62, no. 19, p. 4698. DOI: 10.1016/j.tet.2005.12.065.

    Article  CAS  Google Scholar 

  23. Kafarski, P., Lejczak, B., Kukhar, V.P., Hudson, H.R., Aminophosphonic and Aminophosphinic Acids–Chemistry and Biological Activity, Chichester: John Wiley & Sons, 2000, p. 407.

    Google Scholar 

  24. Yiotakis, A.D., Georgiadis, D., Matziari, M., Makaritis, A., and Dive, V., Curr. Org. Chem., 2004, vol. 8, no. 12, p. 1135. DOI: 10.2174/1385272043370177.

    Article  CAS  Google Scholar 

  25. Mucha, A., Kafarski, P., and Berlicki, L., J. Med. Chem., 2011, vol. 54, no. 17, p. 5955. DOI: 10.1021/jm200587f.

    Article  CAS  Google Scholar 

  26. Adamczeski, M., Quiñoa, E., and Crews, P., J. Am. Chem. Soc., 1988, vol. 110, no. 5, p. 1598. DOI: 10.1021/ja00213a037.

    Article  CAS  Google Scholar 

  27. Rodriguez, J., Nieto, R.M., and Crews, P., J. Nat. Prod., 1993, vol. 56, p. 2034. DOI: 10.1021/np50102a002.

    Article  CAS  Google Scholar 

  28. Rudi, A., Kashman, Y., Benayahu, Y., and Schleyer, M., J. Nat. Prod., 1994, vol. 57, p. 829. DOI: 10.1021/np50108a023.

    Article  CAS  Google Scholar 

  29. Fernández, R., Dherbomez, M., Letourneux, Y., Nabil, M., Verbist, J.F., and Biard, J.F., J. Nat. Prod., 1999, vol. 62, p. 678. DOI: 10.1021/np980330l.

    Article  Google Scholar 

  30. Drach, B.S. and Sviridov, E.P., Zh. Obshch. Khim., 1974, vol. 44, no. 2, p. 348.

    CAS  Google Scholar 

  31. Drach, B.S., Sviridov, E.P., and Shaturskii, Ya.P., Zh. Obshch. Khim., 1974, vol. 44, no. 8, p. 1712.

    CAS  Google Scholar 

  32. Abdurakhmanova, E.R., Lukashuk, E.I., Golovchenko, A.V., Pil’o, S.G., and Brovarets, V.S., Russ. J. Gen. Chem., 2015, vol. 85, no. 4, p. 851. DOI: 10.1134/S1070363215040143.

    Article  CAS  Google Scholar 

  33. Kondratyuk, K.M., Golovchenko, A.V., Osadchuk, T.V., and Brovarets, V.S., Russ. J. Gen. Chem., 2011, vol. 81, no. 7, p. 1470. DOI: 10.1134/S1070363211070115.

    Article  CAS  Google Scholar 

  34. Kondratyuk, K.M., Lukashuk, O.I., Golovchenko, A.V., Komarov, I.V., Brovarets, V.S., and Kukhar, V.P., Tetrahedron, 2013, vol. 69, no. 30, p. 6251. DOI: 10.1016/j.tet.2013.05.017.

    Article  CAS  Google Scholar 

  35. Lukashuk, O., Kondratyuk, K., Golovchenko, A., Brovarets, V., and Kukhar, V., Heteroatom Chem., 2013, vol. 24, p. 289. DOI: 10.1002/hc.21093.

    Article  CAS  Google Scholar 

  36. Kockritz, A. and Schnell, M., Phosphorus, Sulfur, Silicon, Relat. Elem., 1993, vol. 83, nos. 1–4, p. 125.

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 1, Kyiv, 02660, Ukraine

    E. R. Abdurakhmanova, E. I. Lukashuk, A. V. Golovchenko & V. S. Brovarets

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  1. E. R. Abdurakhmanova
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  2. E. I. Lukashuk
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  3. A. V. Golovchenko
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  4. V. S. Brovarets
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Correspondence to V. S. Brovarets.

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Original Russian Text © E.R. Abdurakhmanova, E.I. Lukashuk, A.V. Golovchenko, V.S. Brovarets, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 7, pp. 1106–1118.

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Abdurakhmanova, E.R., Lukashuk, E.I., Golovchenko, A.V. et al. Synthesis and properties of 4-phosphorylated derivatives of 5-hydroxyalkylamino-1,3-oxazoles. Russ J Gen Chem 86, 1584–1596 (2016). https://doi.org/10.1134/S1070363216070094

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  • DOI: https://doi.org/10.1134/S1070363216070094

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