268
ALEKSANYAN, HAMBARDZUMYAN
toluene, 1 : 3). Found, %: C 67.51; H 6.00; N 14.49;
S 8.33. C22H24N4OS. Calculated, %: C 67.35; H 6.12;
N 14.28; S 8.16.
REFERENCES
1. Kumar, S., Bawa, S. and Gupta, H., Mini-
Reviews Med. Chem., 2009, vol. 14, p. 1648.
2. Arancibia, R., Dubar, F., Pradines, B., Forfar, I.,
Dive, D., Hugo, A., Klahn, A., and Biot, Ch.,
Bioorg. Med. Chem., 2010, vol. 18, p. 8085.
3. Mostafa, M.G., Mansour, S.A., Mohammed, S.A.,
Yassin, M.N., and Abdullah, A.A., Chem. Central J.,
2016, vol. 10, p. 18.
N'-[4-(Dimethylamino)benzylidene]-2-(2,8-
dimethylquinolin-4-ylsulfanyl)acetohydrazide (4c).
Yield 0.36 g (95%), mp 216–217°C, Rf 0.67 (ethanol–
toluene, 1 : 3). 1H NMR spectrum, δ, ppm (2 : 3 syn/anti
mixture):2.56s(2H,CH3),2.63s(1H,CH3),2.65–2.70m
(3H, N=C–CH3), 2.93–3.00 m (6H, NCH3), 4.01 and
4.40 s (0.80H and 1.20 H, SCH2), 6.74 d (2Harom, J
8.8 Hz), 7.38–7.63 m (5Harom), 7.85–7.92 m (1Harom),
7.93 and 8.07 s (0.6H and 0.4H, CH=N), 11.38 and
11.48 s (0.4H and 0.6H, NH). Found, %: C 67.28;
H 6.41; N 14.13; S 8.02. C22H24N4OS. Calculated, %:
C 67.35; H 6.12; N 14.28; S 8.16.
4. Mostafa, S., Hussein, A., Abdel-Hamid, N., Kafafy
Samia, G., Abdel-Moty, O.M., and Abou-Ghadir, F.,
Acta Pharm., 2009, vol. 59, p. 365.
5. Denny, W.A., Wilson, W.R., Ware, D.C., Atwell, G.J.,
Milbank, J.B., and Stevenson, R.J., US Patent
no. 2004/O1381.95 A1, 2004; Chem. Abstr., 2006,
no. US 7064117B2.
Compounds 5a–5c (general procedure). A mixture
of 1 mmol of compound 1a–1c [13], 15 mL of dioxane,
and 0.18 g (1.2 mmol) of phthalic anhydride was refluxed
for 7 h with stirring. After cooling, rhe precipitate was
filtered off, washed with dioxane, and recrystallized
from aqueous ethanol.
6. Solomon, V.R. and Lee, C.H.H., Bioorg. Med.
Chem., 2010, vol. 18, p. 1563.
N'-(1,3-Dioxoindolin-2-yl)-2-(2-methylquinolin-
4-ylsulfanyl)acetamide (5a). Yield 0.34 g (90%), mp
220–221°C, Rf 0.54 (ethanol–toluene, 1 : 1). H NMR
7. Mahamoud, A., Chevalier, J., Davin-Regli, A.,
Barbe, J., and Pages, J.M., Curr. Drug Targ., 2006,
vol. 7, p. 843.
1
8. Kumar, A., Srivastava, K., Kumar, R., Puri, S.K.,
and Chauhan, P.M., Bioorg. Med. Chem. Lett.,
2010, vol. 20, p. 7059.
spectrum, δ, ppm: 2.72 s (3H, CH3), 4.11 s (2H,
SCH2), 6.49 s (1Harom), 7.39 m (8Harom), 10.5 br.s (1H,
NH). Found, %: C 63.83; H 3.73; N 11.31; S 8.63.
C20H15N3O3S. Calculated, %: C 63.66; H 3.98; N 11.14;
S 8.49.
9. Vaidya, A, Jain, Sh., Jain, P, Jain, P., Tiwari, N., Jain, R.,
Jain, R., Jain, A.K., and Agrawal, R.K., Mini-Reviews
Med. Chem., 2016, vol. 16, p. 825.
10. Fershtat, L.L., Kulikov, A.S., Ananyev, I.V., Struch-
kova, M.I., and Makhova, N.N., J. Heterocycl. Chem.,
2016, vol. 53, p. 102.
11. Mhaske, P.C., Shelke, S.H., Gadge, K., and Shinde, A., J.
Heterocycl. Chem., 2016, vol. 53, p. 129.
N'-(1,3-Dioxoindolin-2-yl)-2-(2,6-dimethylqui-
nolin-4-ylsulfanyl)acetamide (5b). Yield 0.34 g (87%),
1
mp 228–229°C, Rf 0.52 (ethanol–toluene, 1 : 1). H
NMR spectrum, δ, ppm: 2.49 s (3H, CH3), 2.53 s (3H,
N=C–CH3), 4.16 s (2H, SCH2), 7.42 s (1Harom), 7.46–
7.64 m (3Harom), 7.75–7.98 m (4Harom), 12.99 br.s (1H,
NH). Found, %: C 64.23; H 4.51; N 13.53; S 8.02.
C21H17N3O3S. Calculated, %: C 64.45; H 4.35; N 13.30;
S 8.18.
N'-(1,3-Dioxoindolin-2-yl)-2-(2,8-dimethylqui-
nolin-4-ylsulfanyl)acetamide (5c). Yield 0.36 g (92%),
mp210–211°C,Rf0.58(ethanol–toluene,1:1).Found,%:
C 64.63; H 4.51; N 13.19; S 8.41. C21H17N3O3S. Cal-
culated, %: C 64.45; H 4.35; N 13.30; S 8.18.
12. Malakyan, M.G., Bajinyan, S.A., Vardevanyan, L.A.,
Grigoryan, D.S., Yeghiazaryan, D.E., Avetisyan, A.A.,
Aleksanyan, I.L., Hambardzumyan, L.P., and Sarg-
syan, K.S., Parm. Chem. J., 2009, vol. 43, p. 7.
13. Aleksanyan, I.L. and Hambardzumyan, L.P., Russ. J. Org.
Chem., 2017, vol. 53, p. 226.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 2 2020