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artykuł w czasopiśmie wyróżnionym w JCR

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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY no. 155, pages 670 - 680,
ISSN: 0223-5234

Language:

English

Publication year:

2018

Bibliographic description:

Pogorzelska A., Sławiński J., Kawiak A., Żołnowska B., Chojnacki J., Stasiłojć G., Ulenberg S., Szafrański K., Bączek T.: Synthesis, molecular structure, and metabolic stability of new series of N' -(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-1-(5-phenyl-1 H -pyrazol-1-yl)amidine as potential anti-cancer agents// EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. -Vol. 155, (2018), s.670-680

DOI:

Digital Object Identifier (open in new tab) 10.1016/j.ejmech.2018.06.032

Bibliography: test

1. HRMS (ESI-TOF) open in new tab
2. C, H, N.
3. 1.1.10. N'-{4-Chloro-5-methyl-2-[(2-trifluoromethylphenyl)methylthio]benzenesulfonyl}-1- MeCN (0.115 g, 40%): m.p. 130−133 °C; IR (KBr): 3466, 3354 (NH), 1652 (NH), 1583, 1569, 1528, 1446 (C=C, C=N), 1319, 1134 (SO 2 ) cm -1 ; 1 H NMR (500 open in new tab
4. MHz, DMSO-d 6 ): δ 2.28 (s, 3H, CH 3 ), 2.29 (s, 3H, CH 3 ), 4.35 (s, 2H, SCH 2 ), 6.41 (s, 1H, H- 4 pyrazole), 6.88 (t, 2H, arom.), 7.01−7.05 (m, 3H, arom.), 7.41 (s, 1H, H-3), 7.46−7.49 (m, 2H, H-6, arom.), 7.56 (m, 2H, arom.), 7.70 (d, J = 7.3 Hz, 1H, arom), 7.98 (s, 1H, NH), 8.90 (s, 1H, NH) ppm;
5. HRMS (ESI-TOF) open in new tab
6. C, H, N.
7. 1.1.11. N'-{4-Chloro-5-methyl-2-[(3-trifluoromethylphenyl)methylthio]benzenesulfonyl}-1- MeCN (0.088 g, 31%): m.p. 121−124 °C; IR (KBr): 3432, 3404 (NH), 1655 (NH), 1532, 1464, 1446, 1427 (C=C, C=N), 1330, 1126 (SO 2 ) cm -1 ; 1 H NMR (200 open in new tab
8. MHz, DMSO-d 6 ): δ 2.29 (s, 3H, CH 3 ), 4.40 (s, 2H, SCH 2 ), 6.60 (d, J = 1.7 Hz, 1H, H-4
9. pyrazole), 6.79−7.06 (m, 5H, arom.), 7.40−7.73 (m, 6H, arom.), 7.94 (d, J = 1.6 Hz, 1H, H-3 pyrazole), 8.22 (s, 1H, NH), 9.19 (s, 1H, NH) ppm; open in new tab
10. HRMS (ESI-TOF) m/z calcd for C 25 H 20 ClF 3 N 4 O 2 S 2 [M+H + ] 565.0741, found 565.0737. Anal. (C 25 H 20 F 3 ClN 4 O 2 S 2 ) C, H, N. open in new tab
11. 1.1.12. N'-{4-Chloro-5-methyl-2-[(3-trifluoromethylphenyl)methylthio]benzenesulfonyl}-1- MeCN (0.103 g, 35%): m.p. 146−148 °C; IR (KBr): 3442, 3353 (NH), 1638 (NH), 1560, 1533, 1479, 1436 (C=C, C=N), 1291, 1139 (SO 2 ) cm -1 ; 1 H NMR (500 open in new tab
12. MHz, DMSO-d 6 ): δ 2.26 (s, 3H, CH 3 ), 2.28 (s, 3H, CH 3 ), 4.38 (s, 2H, SCH 2 ), 6.39 (s, 1H, H- 4 pyrazole), 6.77 (t, 2H, arom.), 6.84 (d, J = 7.3 Hz, 2H, arom.), 7.00 (t, 1H, arom.), 7.38 (t, 1H, arom.), 7.42 (s, 1H, H-3), 7.51−7.54 (m, 2H, H-6, arom.), 7.60 (d, J = 7.9 Hz, 1H, arom.), 7.70 (s, 1H, arom.), 8.04 (s, 1H, NH), 8.96 (s, 1H, NH) ppm. 13 C NMR (125 MHz, DMSO- Hz, 1H, arom.), 7.44−7.46 (m, 2H, arom., H-3), 7.54 (s, 1H, H-6), 7.91 (s, 1H, H-3 pyrazole), 8.11 (s, 1H, NH), 9.09 (s, 1H, NH) ppm;
13. HRMS (ESI-TOF) open in new tab
14. M+H + ] 531.0477, found 531.0428. Anal. (C 24 H 20 Cl 2 N 4 O 2 S 2 ) C, H, N. 4.1.1.16. N'-{4-Chloro-2-[(2-chlorophenyl)methylthio]-5-methylbenzenesulfonyl}-1-(3- MeCN (0.128 g, 47%): m.p. 135−138 °C; IR (KBr): 3463, 3349 (NH), 1638 (NH), 1558, 1521, 1472, 1446 (C=C, C=N), 1291, 1134 (SO 2 ) cm -1 ; 1 H NMR (500 open in new tab
15. MHz, DMSO-d 6 ): δ 2.29 (s, 6H, 2×CH 3 ), 4.35 (s, 2H, SCH 2 ), 6.38 (s, 1H, H-4 pyrazole), 6.78 (t, 2H, arom.), 6,93 (d, J = 7.3 Hz, 2H, arom.), 6.99 (t, 1H, arom.), 7.20−7.26 (m, 2H, arom.), 7.35 (d, J = 7.3 Hz, 1H, arom.), 7.44−7.46 (m, 2H, arom., H-3), 7.54 (s, 1H, H-6), 7.96 (s, 1H, NH), 8.89 (s, 1H, NH) ppm;
16. HRMS (ESI-TOF) open in new tab
17. C, H, N. 4.1.1.17. N'-{4-Chloro-2-[(3-chlorophenyl)methylthio]-5-methylbenzenesulfonyl}-1-(5- MeCN (0.113 g, 42%): m.p. 124−127 °C; IR (KBr): 3417 (NH), 1655 open in new tab
18. (NH), 1541, 1462, 1425 (C=C, C=N), 1289, 1133 (SO 2 ) cm -1 ; 1 H NMR (500 MHz, DMSO- d 6 ): δ 2.28 (s, 3H, CH 3 ), 4.27 (s, 2H, SCH 2 ), 6.59 (s, 1H, H-4 pyrazole), 6.85 (t, 2H, arom.), 6.96 (d, J = 7.3 Hz, 2H, arom.), 7.04 (t, 1H, arom.), 7.19−7.28 (m, 3H, arom.), 7.40 (s, 1H, arom.), 7.46 (s, 1H, H-3), 7.49 (s, 1H, H-6), 7.91 (s, 1H, H-3 pyrazole), 8.19 (s, 1H, NH), 9.17 (s, 1H, NH) ppm;
19. HRMS (ESI-TOF) open in new tab
20. C, H, N.
21. 1.1.18. N'-{4-Chloro-2-[(3-chlorophenyl)methylthio]-5-methylbenzenesulfonyl}-1-(3- MeCN (0.096 g, 35%): m.p. 108−111 °C; IR (KBr): 3463, 3349 (NH), 1638 (NH), 1558, 1521, 1472, 1446 (C=C, C=N), 1291, 1134 (SO 2 ) cm -1 ; 1 H NMR (500 open in new tab
22. MHz, DMSO-d 6 ): δ 2.27 (s, 3H, CH 3 ), 2.29 (s, 3H, CH 3 ), 4.29 (s, 2H, SCH 2 ), 6.40 (s, 1H, H-4
23. pyrazole), 6.81 (t, 2H, arom.), 6,91 (d, J = 7.3 Hz, 2H, arom.), 7.02 (t, 1H, arom.), 7.20−7.25 (m, 2H, arom.), 7.28 (d, J = 7.3 Hz, 1H, arom.), 7.39 (s, 1H, arom.), 7.43 (s, 1H, H-3), 7.51 (s, 1H, H-6), 8.03 (s, 1H, NH), 8.96 (s, 1H, NH) ppm;
24. HRMS (ESI-TOF) m/z calcd for C 25 H 22 Cl 2 N 4 O 2 S 2 [M+H + ] 545.0634, found 545.0606. Anal. (C 25 H 22 Cl 2 N 4 O 2 S 2 ) C, H, N. 4.1.1.19. N'-{4-Chloro-2-[(4-chlorophenyl)methylthio]-5-methylbenzenesulfonyl}-1-(5- MeCN (0.089 g, 33%): m.p. 147−150 °C; IR (KBr): 3446, 3331 (NH), 1648 (NH), 1534, 1491, 1461, 1427 (C=C, C=N), 1291, 1137 (SO 2 ) cm -1 ; 1 H NMR (500
25. MHz, DMSO-d 6 ): δ 2.28 (s, 3H, CH 3 ), 4.26 (s, 2H, SCH 2 ), 6.59 (s, 1H, H-4 pyrazole), 6.87 (t, 2H, arom.), 6.95 (d, J = 7.3 Hz, 2H, arom.), 7.05 (t, 1H, arom.), 7.23 (d, J = 8.3 Hz, 2H, arom.), 7.31 (d, J = 8.3 Hz, 2H, arom.), 7.46 (s, 1H, H-3), 7.50 (s, 1H, H-6), 7.93 (s, 1H, H-3 pyrazole), 8.18 (s, 1H, NH), 9.17 (s, 1H, NH) ppm;
26. HRMS (ESI-TOF) m/z calcd for C 24 H 20 Cl 2 N 4 O 2 S 2 [M+H + ] 531.0477, found 531.0454. Anal. (C 24 H 20 Cl 2 N 4 O 2 S 2 ) C, H, N. 4.1.1.20. N'-{4-Chloro-2-[(4-chlorophenyl)methylthio]-5-methylbenzenesulfonyl}-1-(3- MeCN (0.109 g, 40%): m.p. 135−138 °C; IR (KBr): 3457, 3343 (NH), 1648 (NH), 1532, 1508, 1491, 1446, 1422 (C=C, C=N), 1284, 1135 (SO 2 ) cm -1 ; 1 H NMR (500 MHz, DMSO-d 6 ): δ 2.27 (s, 3H, CH 3 ), 2.30 (s, 3H, CH 3 ), 4.27 (s, 2H, SCH 2 ), 6.41 (s, 1H, H-4 pyrazole), 6.83 (t, 2H, arom.), 6,91 (d, J = 7.8 Hz, 2H, arom.), 7.03 (t, 1H, arom.), 7.22 (d, J = 8.3 Hz, 2H, arom.), 7.32 (d, J = 8.3 Hz, 2H, arom.), 7.43 (s, 1H, H-3), 7.52 (s, 1H, H-6), 8.01 (s, 1H, NH), 8.97 (s, 1H, NH) ppm; open in new tab
27. HRMS (ESI-TOF) m/z calcd for C 25 H 22 Cl 2 N 4 O 2 S 2 [M+H + ] 545.0634, found 545.0613. Anal. (C 25 H 22 Cl 2 N 4 O 2 S 2 ) C, H, N. 4.1.1.21. N'-[4-Chloro-5-methyl-2-(naphthalene-1-ylmethylthio)benzenesulfonyl]-1-(5- EtOH (0.148 g, 54%): m.p. 155−158 °C; IR (KBr): 3404, 3309 (NH), 1646 (NH), 1539, 1462, 1427 (C=C, C=N), 1288, 1129 (SO 2 ) cm -1 ; 1 H NMR (500 MHz, DMSO-d 6 ): δ 2.29 (s, 3H, CH 3 ), 4.73 (s, 2H, SCH 2 ), 6.53 (s, 1H, H-4 pyrazole), 6.74 (t, 2H, arom.), 6.83 (d, J = 7.4 Hz, 2H, arom.), 6.97 (t, 1H, arom.), 7.38−7.43 (m, 3H, arom.), 7.46 (s, 1H, H-3), 7.55 (d, J = 7.3 Hz, 1H, arom.), 7.67 (s, 1H, H-6), 7.80 (d, J = 8.3 Hz, 1H, arom.), open in new tab
28. HRMS (ESI-TOF) m/z calcd for C 28 H 23 ClN 4 O 2 S 2 [M+H + ] 547.1024, found 545.1030. Anal. (C 28 H 23 ClN 4 O 2 S 2 ) C, H, N. 4.1.1.22. N'-[4-Chloro-5-methyl-2-(naphthalene-1-ylmethylthio)benzenesulfonyl]-1-(3- EtOH (0.152 g, 54%): m.p. 131−135 °C; IR (KBr): 3424, 3318 (NH), 1643 (NH), 1533, 1507, 1446, 1424 (C=C, C=N), 1287, 1132 (SO 2 ) cm -1 ; 1 H NMR (500
29. MHz, DMSO-d 6 ): δ 2.29 (s, 6H, 2×CH 3 ), 4.75 (s, 2H, SCH 2 ), 6.32 (s, 1H, H-4 pyrazole), 6.69 (t, 2H, arom.), 6,75 (d, J = 7.8 Hz, 2H, arom.), 6.95 (t, 1H, arom.), 7.37−7.44 (m, 4H, arom.
30. H-3), 7.55 (d, J = 6.9 Hz, 1H, arom.), 7.70 (s, 1H, H-6), 7.79 (d, J = 8.3 Hz, 1H, arom.), 7.82 (d, J = 7.3 Hz, 1H, arom.), 7.92 (s, 1H, NH), 8.14 (d, J = 7.8 Hz, 1H, arom.), 8.79 (s, 1H, NH) ppm; open in new tab
31. HRMS (ESI-TOF) m/z calcd for C 29 H 25 ClN 4 O 2 S 2 [M+H + ] 561.1180, found 561.1187. Anal. (C 29 H 25 ClN 4 O 2 S 2 ) C, H, N. open in new tab
32. 1.1.23. N'-{4-Chloro-2-[(6-chlorobenzo[d][1,3]dioxol-5-yl)methylthio]-5- methylbenzenesulfonyl}-1-(5-phenyl-1H-pyrazol-1-yl)MeCN (0.157 g, 54%): m.p. 149−152 °C; IR (KBr): 3402, 3307, 3278 open in new tab
33. H NMR (200 MHz, DMSO-d 6 ): δ 2.31 (s, 3H, CH 3 ), 4.25 (s, 2H, SCH 2 ), 5.98 (s, 2H, OCH 2 O), 6.58 (d, J = 1.7 Hz, 1H, H-4 pyrazole), 6.78−6.87 (m, 2H, arom.), 6.94−7.08 (m, 5H, arom.)7.47 (s, 1H, H-3), 7.57 (s, 1H, H-6), 7.90 (d, J = 1.7 Hz, 1H, H-3 pyrazole), 8.10 (s, 1H, NH), 9.07 (s, 1H, NH) ppm; open in new tab
34. HRMS (ESI-TOF) open in new tab
35. M+H + ] 575.0376, found 575.0379. Anal. (C 25 H 20 Cl 2 N 4 O 4 S 2 ) C, H, N. open in new tab
36. 1.1.24. N'-{4-Chloro-2-[(6-chlorobenzo[d][1,3]dioxol-5-yl)methylthio]-5- methylbenzenesulfonyl}-1-(3-methyl-5-phenyl-1H-pyrazol-1-yl)amidine (60) MeCN (0.065 g, 22%): m.p. 158−161 °C; IR (KBr): 3442, 3332 (NH), 1642 (NH), 1569, 1534, 1504, 1475, 1449, 1431 (C=C, C=N), 1286, 1134 (SO 2 ) cm -1 ; 1 H NMR (200 MHz, DMSO-d 6 ): δ 2.29 (s, 6H, 2×CH 3 ), 4.26 (s, 2H, SCH 2 ), 5.97 (s, 2H, OCH 2 O), 6.40 (s, 1H, H-4 pyrazole), 6.76−6.83 (m, 2H, arom.), 6.94−7.06 (m, 5H, arom.), 7.44 (s, 1H, H-3), 7.58 (s, 1H, H-6), 7.96 (s, 1H, NH), 8.88 (s, 1H, NH) ppm;
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92. HCT-116 and HeLa cell lines were the most susceptible for tested compounds. Four compounds display 4-fold higher activity against HeLa than HaCaT cells. Active compounds cause DNA fragmentation in HCT-116 and HeLa cells. open in new tab

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Gdańsk University of Technology