RAFIEE POUR et al.
858
7.23 d (2H, J = 6.8 Hz), 13.65 s (1H, NH). 13C NMR
spectrum, δC, ppm: 14.3, 29.5, 124.1, 127.1, 128.7,
129.0, 129.7, 130.5, 137.3, 138.5, 143.8, 150.3, 163.2,
165.1. Found, %: C 52.16; H 3.69; N 13.57.
C18H16N4O4S2. Calculated, %: C 51.91; H 3.87;
N 13.45.
6. Košak, U., Knez, D., Coquelle, N., Brus, B., Pišlar, A.,
Nachon, F., Brazzolotto, X., Kos, J., Colletier, J.-P., and
Gobec, S., Bioorg. Med. Chem., 2017, vol. 25, no. 2,
p. 633.
7. Alaoui, S., Dufies, M., Driowya, M., Demange, L.,
Bougrin, K., Robert, G., Auberger, P., Pagès, G., and
Benhida, R., Bioorg. Med. Chem. Lett., 2017, vol. 27,
no. 9, p. 1989.
N-[4-(Naphthalen-2-ylsulfamoyl)-1,3-thiazol-
2-yl]-4-nitrobenzamide (5k). Yield 76%, cream solid,
mp 225–230°C, Rf 0.3. IR spectrum, ν, cm–1: 3285
(N–H), 1678 (C=O), 1142, 1346 (SO2). 1H NMR spec-
trum, δ, ppm: 7.33 d (1H, J = 7.2 Hz), 7.85 s (J =
10 Hz), 7.87 s (2H, J = 8 Hz), 7.94 t (1H, J = 5.2,
3.6 Hz), 8.127 t (1H, J = 3.6 Hz), 8.31 d (2H, J =
8.8 Hz), 8.39 d (2H, J = 8.8 Hz). 13C NMR spectrum,
δC, ppm: 123.5, 124.0, 124.1, 126.1, 126.7, 126.8,
127.7, 128.8, 130.0, 130.83, 130.5, 132.3, 134.4, 150.3.
Found, %: C 54.86; H 3.15; N 12.62. C20H14N4O4S2.
Calculated, %: C 54.79; H 3.22; N 12.78.
8. Chhabria, M.T., Patel, S., Modi, P., and
Brahmkshatriya, P.S., Curr. Top. Med. Chem., 2016,
vol. 16, no. 26, p. 2841.
9. Das, J., Furch, J.A., Liu, C., Moquin, R.V., Lin, J.,
Spergel, S.H., McIntyre, K.W., Shuster, D.J.,
O’Day, K.D., and Penhallow, B., Bioorg. Med. Chem.
Lett., 2006, vol. 16, no. 14, p. 3706.
10. Piechowicz, K.A., Truong, E.C., Javed, K.M.,
Chaney, R.R., Wu, J.Y., Phuan, P.W., Verkman, A.S.,
and Anderson, M.O., J. Enzyme Inhib. Med. Chem.,
2016, vol. 31, no. 6, p. 1362.
11. Kretschmer, S.B.M., Woltersdorf, S., Rödl, C.B.,
Vogt, D., Häfner, A.-K., Steinhilber, D., Stark, H., and
Hofmann, B., Future Med. Chem., 2016, vol. 8, no. 2,
p. 149.
N-[4-(Dipropylsulfamoyl)-1,3-thiazol-2-yl)-
4-nitrobenzamide (5l). Yield 76%, cream solid,
mp 236–240°C, Rf 0.3. IR spectrum, ν, cm–1: 3076
(N–H, amide), 1675 (C=O), 1149, 1303 (SO2).
1H NMR spectrum, δ, ppm: 0.93 t (6H, J = 8.4 Hz),
1.56 s (4H), 3.08 t (4H, J = 8.7 Hz), 8.16 s (1H), 8.33 d
(2H, J = 8.8 Hz), 8.42 d (2H, J = 8.8 Hz), 13.63 s (1H,
NH). 13C NMR spectrum, δC, ppm: 11.4, 22.3, 124.1,
128.3, 130.4, 142.8, 150.3, 162.6, 165.1. Found, %:
C 48.62; H 4.97; N 14.05. C16H20N4O4S2. Calculated,
%: C 48.47; H 5.08; N 14.13.
12. Urbanek, R.A., Xiong, H., Wu, Y., Blackwell, W.,
Steelman, G., Rosamond, J., Wesolowski, S.S., Camp-
bell, J.B., Zhang, M., and Brockel, B., Bioorg. Med.
Chem. Lett., 2013, vol. 23, no. 2, p. 543.
13. Gao, W.-W., Gopala, L., Bheemanaboina, R.R.Y.,
Zhang, G.-B., Li, S., and Zhou, C.-H., Eur. J. Med.
Chem., 2018, vol. 146, p. 15.
14. Das, D., Sikdar, P., and Bairagi, M., Eur. J. Med.
Chem., 2016, vol. 109, p. 89.
CONFLICT OF INTERESTS
15. Jain, N. and Singh, B., World J. Res. Rev., 2016, vol. 3,
no. 5, p. 52.
16. Čapkauskaitė, E., Zubrienė, A., Paketurytė, V.,
Timm, D.D., Tumkevičius, S., and Matulis, D., Bioorg.
Chem., 2018, vol. 77, p. 534.
The authors declare the absence of conflict of
interests.
17. Awadallah, F.M., Bua, S., Mahmoud, W.R., Nada, H.H.,
Nocentini, A., and Supuran, C.T., J. Enzyme Inhib. Med.
Chem., 2018, vol. 33, no. 1, p. 629.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 6 2019