NANOSCALED INCLUSION COMPLEXES OF β-CYCLODEXTRIN
757
1
(30%), mp 277–278°С (decomp.). Н NMR spectrum
(DMSO-d6), δ, ppm (J, Hz): β-cyclodextrin, 3.34–3.68
m (84Н, С2Н–С5Н, С6Н2), 4.15–4.17 m (14Н, С6ОН),
4.85–4.86 br.s (14Н, С1Н), 5.44–5.47 br.s (28Н,
С2ОН, С3ОН); diol IX, 1.90–1.94 m (4Н, СН2СН2),
4.43–4.45 m (4Н, СН2О), 7.81–7.82 m (4H, NCHCH),
8.79–8.80 m (4H, NCH). Found, %: С 46.83; Н 6.15;
N 1.05. С100Н156N2О74. Calculated, %: С 46.73; Н
6.12; N 1.09.
С2Н–С5Н, С6Н2), 4.20–4.22 m (7Н, С6ОН), 4.85–4.86
br.s (7Н, С1Н), 5.49–5.52 br.s (14Н, С2ОН, С3ОН);
diol VI, 4.70 br.s (4Н, СН2О), 7.55–7.58 d.d [2Н,
NСHСHСHСС(О), 3J 4.9], 8.28–8.30 d.d [2Н,
3
4
NСHСHСHСС(О)О, J 7.9, J 2.1], 8.81–8.82 d.d
3
4
[2Н, NСHСHСHСС(О), J 7.9, J 1.7], 9.10 d [2H,
4
NCHCC(O), J 1.7]. Found, %: С 47.91; Н 5.77; N
1.89. С56Н82N2О39. Calculated, %: С 47.80; Н 5.87; N
1.99.
Inclusion complex of β-cyclodextrin with О,О'-
bisbenzoyl-1,3-propylenediol (XV) was prepared
similarly from 0.227 g of β-cyclodextrin and 0.0284 g
of diol II in 10 mL of water. Yield 0.078 g (55%), mp
ACKNOWLEDGMENTS
This work was financially supported by Russian
Foundation for Basic Research (project no. 12-03-
00147a).
1
254–256°С (decomp.), Rf 0.68 (C). Н NMR spectrum
REFERENCES
(DMSO-d6), δ, ppm (J, Hz): β-cyclodextrin, 3.32–3.71
m (42Н, С2Н–С5Н, С6Н2), 4.38–4.51 m (7Н, С6ОН),
4.73–4.79 br.s (7Н, С1Н), 5.59–5.68 br.s (7Н, С3ОН),
5.69–5.73 br.s (7Н, С2ОН); diol II, 2.12–2.21 m (2Н,
СН2СН2СН2), 4.39–4.41 m (4Н, СН2О), 7.45 t (4Н,
1. Kurochkina, G.I., Kudryavtseva, N.A., Grachev, M.K.,
Lysenko, S.A., Vasyanina, L.K., and Nifant’ev, E.E.,
Russ. J. Gen. Chem., 2007, vol. 77, no. 3, p. 442;
Senyushkina, I.A., Kurochkina, G.I., Grachev, M.K.,
Grinberg, V.A., Batalova, T.A., and Nifant’ev, E.E.,
Russ. J. Gen. Chem., 2009, vol. 79, no. 6, p. 1167;
Grachev, M.K., Senyushkina, I.A., Kurochkina, G.I.,
Lysenko, K.A., Vasyanina, L.K., and Nifant’ev, E.E.,
Russ. J. Gen. Chem., 2010, vol. 46, no. 10, p. 1933.
2. Sergievich A.A., Grachev, M.K., Kurochkina, G.I.,
Batalova, T.A., and Plastinin, M.L., Yakut. Med. Zh.,
2011, no. 1, p. 101; Batalova, T.A., Dorovskikh, V.A.,
Grachev, M.K., Kurochkina, G.I., Charaev, A.A.,
Plastinin, M.L., and Sergievich, A.A., Vopr. Eksp. Biol. i
Med., 2011, no. 1, p. 42.
3. Grachev, M.K., Charaev, A.A., Kurochkina, G.I.,
Batalova, T.A., Soboleva, N.O., Vasyanina, L.K., and
Nifant’ev, E.E., Russ. J. Gen. Chem., 2011, vol. 81,
no. 10, p. 2129.
4. Geze, A., Aous, S., Baussane, I., Putaux, J.L., Defaye, J.,
and Wouessiddjewe, D.G., Int. J. Pharm., 2002, vol. 242,
p. 301.
3
3
С6Нmeta, J 7.8), 7.61 t (2Н, С6Нpara, J 7.3), 7.93 d
3
(4Н, С6Нortho, J 7.3). Found, %: С 50.05; Н 6.20.
С59Н86О39. Calculated, %: С 49.93; Н 6.11.
Inclusion complex of β-cyclodextrin with О,О'-
bisbenzoyl-2,2-dimethyl-1,3-propylenediol (XVI) was
prepared similarly from 0.227 g of β-cyclodextrin and
0.0312 g of diol IV in 4 mL of water. Yield 0.068 g
1
(47%), mp 272–274°С (decomp.), Rf 0.51 (C). Н
NMR spectrum (DMSO-d6), δ, ppm (J, Hz): β-cyclo-
dextrin, 3.21–3.69 m (42Н, С2Н–С5Н, С6Н2), 4.42–
4.45 m (7Н, С6ОН), 4.77–4.83 br.s (7Н, С1Н), 5.61–
5.75 br.s (7Н, С3ОН); 5.76–5.80 br.s (7Н, С2ОН); diol
IV, 1.08 s (6Н, СН3), 4.17 s (4Н, СН23О), 7.48 t (4Н,
3
С6Нmeta, J 7.8), 7.62 t (2Н, С6Нpara, J 7.8), 7.95 d
3
(4Н, С6Нortho, J 7.3). Found, %: С 50.75; Н 6.17.
С61Н90О39. Calculated, %: С 50.62; Н 6.27.
Inclusion complex of β-cyclodextrin with О,О'-
bisnicotinoyl-1,2-ethylenediol (XVII) was prepared
similarly from 0.363 g of β-cyclodextrin and 0.0436 g
of diol VI in 10 mL of water. Yield 0.092 g (41%), mp
306–307°С (decomp.). 1Н NMR spectrum (DMSO-d6),
δ, ppm (J, Hz): β-cyclodextrin, 3.32–3.68 m (42Н,
5. Rajewski, R.A. and Stella, V.J., J. Pharm. Sci., 1996,
vol. 85, p. 1142.
6. Sliwa, W. and Grizek, T., Chem. Heterocycl. Comp.,
2005, vol. 41, no. 11, p. 1343.
7. Bourne, J.E., Stacey, M., Tatlow, J.C., and Tedder, J.M.,
J. Am. Chem. Soc., 1949, vol. 69, p. 2976.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 4 2014