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Amphiphilic α-cyclodextrin derivatives containing residues of pharmacologically important acids

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Abstract

New representatives of amphiphilic α-cyclodextrin derivatives containing residues of pharmacologically important acids both at the primary and secondary hydroxyl groups were synthesized using acyl chlorides of palmitic acid and a series of aromatic monocarboxylic acids. The acyl chloride groups were assigned to the positions C(2), C(3), or C(6) of the carbohydrate fragments of α-cyclodextrin by 13C NMR spectroscopy.

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References

  1. R. A. Rajewski, V. J. Stella, J. Pharm. Sci., 1996, 85, 1142.

    Article  CAS  Google Scholar 

  2. K. Uekama, F. Hirayama, T. Irie, Chem. Rev., 1998, 98, 2045.

    Article  CAS  Google Scholar 

  3. M. E. Davis, M. E. Brewster, Nature Rev., Drug Discovery, 2004, 3, 1023.

    Article  CAS  Google Scholar 

  4. R. Challa, A. Ahuja, J. Ali, R. K. Khar, AAPS PharmSciTech, 2005, 6, Arcticle 43, E329; http://www.aapspharm-scitech.org.

    Article  Google Scholar 

  5. E. Memisoglu, A. Bochot, M. Sen, D. Charon, D. Duchêne, A. A. Hincal, J. Pharm. Sci., 2002, 91, 1214; E. Memisoglu, A. Bochot, M. Oezalp, M. Sen, D. Duchêne, A. A. Hincal, Pharm. Res., 2003, 20, 117; A. Geze, S. Aous, I. Baussanne, J. L. Putaux, J. Defaye, D. Wouessidjewe, Int. J. Pharm., 2002, 242, 301; M. Roux, B. Perly, F. Djedaïni-Pilard, Eur. Biophys. J., 2007, 36, 861; E. Bilensoy, J. Biomed. Nanotech., 2008, 4, 293; R. H. de Rossi, O. F. Silva, R. V. Vico, C. J. Gonzalez, Pure Appl. Chem., 2009, 81, 755; H. Parrot-Lopeza, F. Perreta, B. Bertino-Ghera, Ann. Pharm. Franc., 2010, 68, 12.

    Article  CAS  Google Scholar 

  6. I. Javierre, M. Nedyalkov, V. Petkova, J.-J. Benattar, S. Weisse, R. Auzely-Velty, F. Djedaïni-Pilard, B. Perly, J. Colloid Interface Sci., 2002, 254, 120; S. Moutard, B. Perly, P. Gode, G. Demailly, F. Djedaïni-Pilard, J. Inclusion Phenom. Macr. Chem., 2003, 44, 317.

    Article  CAS  Google Scholar 

  7. B. Perly, S. Moutard, F. Djedaïni-Pilard, PharmaChem., 2005, 4, 4.

    CAS  Google Scholar 

  8. M. K. Grachev, S. V. Sipin, L. O. Kononov, E. E. Nifant’ev, Izv. Akad. Nauk, Ser. Khim., 2009, 221 [Russ. Chem. Bull., Int. Ed., 2009, 58, 223].

    Google Scholar 

  9. T. Kida, T. Ohe, H. Higashimoto, H. Harada, Y. Nakatsuji, I. Ikeda, M. Akashi, Chem. Lett., 2004, 33, 258.

    Article  CAS  Google Scholar 

  10. K. Kobayashi, K. Kajikawa, H. Sasabe, W. Knoll, Thin Solid Films, 1999, 349, 244.

    Article  CAS  Google Scholar 

  11. N. Badi, N. Jarroux, P. Guegan, Tetrahedron Lett., 2006, 47, 8925; A. Benkhaled, H. Cheradame, O. Fichet, D. Teyssie, W. Buchmann, P. Guegan, Carbohydr. Polym., 2008, 73, 482.

    Article  CAS  Google Scholar 

  12. J. Szejtli, Chem. Rev., 1998, 98, 1743.

    Article  CAS  Google Scholar 

  13. H. Parrot-Lopez, F. Djedaïni, B. Perly, A. W. Coleman, H. Galons, M. Miocque, Tetrahedron Lett., 1990, 31, 1999; F. Djedaïni-Pilard, J. Désalos, B. Perly, Tetrahedron Lett., 1993, 34, 2457; M. K. Hristova-Kazmierski, P. Horan, P. Davis, H. I. Yamamura, T. Kramer, R. Horvath, W. M. Kazmierski, F. Porreca, V. J. Hruby, Bioorg. Med. Chem. Lett., 1993, 3, 831; K. Uekama, K. Minami, F. Hirayama, J. Med. Chem., 1997, 40, 2755; K. Minami, F. Hirayama, K. Uekama, J. Pharm. Sci., 1998, 87, 715; S. Tavornvipas, H. Arima, F. Hirayama, K. Uekama, T. Ishiguro, M. Oka, K. Hamayasu, H. Hashimoto, J. Inclusion Phenom. Macr. Chem., 2002, 44, 391.

    Article  CAS  Google Scholar 

  14. G. I. Kurochkina, N. A. Kudryavtseva, M. K. Grachev, S. A. Lyssenko, L. K. Vasyanina, E. E. Nifant’ev, Zh. Obshch. Khim., 2007, 77, 477 [Russ. J. Gen. Chem. (Engl. Transl.), 2007, 77, 442]; G. I. Kurochkina, N. A. Kudryavtseva, M. K. Grachev, S. A. Lyssenko, E. E. Nifant’ev, Zh. Obshch. Khim., 2007, 77, 485 [Russ. J. Gen. Chem. (Engl. Transl.), 2007, 77, 450]; M. K. Grachev, A. A. Charaev, G. I. Kurochkina, L. K. Vasyanina, V. N. Shmeleva, E. E. Nifant’ev, Zh. Obshch. Khim., 2010, 80, 1494 [Russ. J. Gen. Chem. (Engl. Transl.), 2010, 80, 1812].

    Google Scholar 

  15. T. A. Batalova, V. A. Dorovskikh, A. A. Sergievich, M. L. Plastinin, M. K. Grachev, G. I. Kurochkina, S. A. Lyssenko, Dal’nevost. Med. Zh. [Far Eastern Medical Journal], 2008, 105 (in Russian); T. A. Batalova, V. A. Dorovskikh, G. I. Kurochkina, M. K. Grachev, A. A. Sergievich, M. L. Plastinin, Byul. Eksperim. Biol. Med. [Experimental Biological Medical Bulletin], 2011, 642 (in Russian); T. A. Batalova, V. A. Dorovskikh, M. K. Grachev, G. I. Kurochkina, A. A. Charaev, M. L. Plastinin, A. A. Sergievich, Voprosy Biol., Med. Farm. Khim. [Problems of Biology, Medical Pharmaceutical Journal], 2011, No. 1, 42 (in Russian).

  16. Pat. RF No. 2363473, 2008; Byul. Izobr. [Invention Bulletin], 2009, 22; Pat. RF No. 2428205, 2010; Byul. Izobr. [Invention Bulletin], 2011, 25; Pat. RF. No. 2429017, 2010; Byul. Izobr. [Invention Bulletin], 2011, 26; A. A. Sergievich, M. K. Grachev, G. I. Kurochkina, T. A. Batalova, M. L. Plastinin, Yakutsk. Med. Zh. [Yakutsk Medical Journal], 2011, No. 1,101 (in Russian).

  17. A. E. Glazyrin, A. N. Syrtsev, G. I. Kurochkina, L. O. Kononov, M. K. Grachev, E. E. Nifant’ev, Izv. Akad. Nauk, Ser. Khim., 2003, 225 [Russ. Chem. Bull., Int. Ed., 2003, 52, 237].

    Google Scholar 

  18. M. K. Grachev, A. V. Edunov, G. I. Kurochkina, A. V. Popkov, I. I. Levina, E. E. Nifant’ev, Zh. Org. Khim., 2011, 41, 290 [Russ. J. Org. Chem. (Engl. Transl.), 2011, 47, 284].

    Google Scholar 

  19. M. K. Grachev, A. V. Edunov, G. I. Kurochkina, I. I. Levina, E. E. Nifant’ev, Zh. Obshch. Khim., 2011, 81, 222 [Russ. J. Gen. Chem. (Engl. Transl.), 2011, 81, 322].

    Google Scholar 

  20. K. Takeo, H. Mitoh, K. Uemura, Carbohydr. Res., 1989, 187, 203; H. H. Baer, Ya. Shen, F. S. González, A. V. Berenguel, J. I. García, Carbohydr. Res., 1992, 235, 129; S. Hanessian, A. Benalil, C. Laferrière, J. Org. Chem., 1995, 60, 4786; D. Rong, V. T. D’souza, Tetrahedron Lett., 1990, 31, 4275.

    Article  CAS  Google Scholar 

  21. A. Harada, A. Hashidzume, Y. Takashima, Adv. Polym. Sci., 2006, 201, 1.

    Article  CAS  Google Scholar 

  22. P. Fügedi, Carbohydr. Res., 1989, 192, 366.

    Article  Google Scholar 

  23. W. Zhang, M. J. Robins, Tetrahedron Lett., 1992, 33, 1177.

    Article  CAS  Google Scholar 

  24. K. Takeo, K. Uemura, H. Mitoh, J. Carbohydr. Chem., 1988, 7, 293.

    Article  CAS  Google Scholar 

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Correspondence to A. V. Edunov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 178–184, January, 2012.

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Grachev, M.K., Edunov, A.V., Kurochkina, G.I. et al. Amphiphilic α-cyclodextrin derivatives containing residues of pharmacologically important acids. Russ Chem Bull 61, 181–187 (2012). https://doi.org/10.1007/s11172-012-0025-6

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  • DOI: https://doi.org/10.1007/s11172-012-0025-6

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