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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R. A. Rajewski, V. J. Stella, J. Pharm. Sci., 1996, 85, 1142.
K. Uekama, F. Hirayama, T. Irie, Chem. Rev., 1998, 98, 2045.
M. E. Davis, M. E. Brewster, Nature Rev., Drug Discovery, 2004, 3, 1023.
R. Challa, A. Ahuja, J. Ali, R. K. Khar, AAPS PharmSciTech, 2005, 6, Arcticle 43, E329; http://www.aapspharm-scitech.org.
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.
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.
B. Perly, S. Moutard, F. Djedaïni-Pilard, PharmaChem., 2005, 4, 4.
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].
T. Kida, T. Ohe, H. Higashimoto, H. Harada, Y. Nakatsuji, I. Ikeda, M. Akashi, Chem. Lett., 2004, 33, 258.
K. Kobayashi, K. Kajikawa, H. Sasabe, W. Knoll, Thin Solid Films, 1999, 349, 244.
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.
J. Szejtli, Chem. Rev., 1998, 98, 1743.
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.
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].
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).
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).
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].
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].
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].
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.
A. Harada, A. Hashidzume, Y. Takashima, Adv. Polym. Sci., 2006, 201, 1.
P. Fügedi, Carbohydr. Res., 1989, 192, 366.
W. Zhang, M. J. Robins, Tetrahedron Lett., 1992, 33, 1177.
K. Takeo, K. Uemura, H. Mitoh, J. Carbohydr. Chem., 1988, 7, 293.
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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