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Publikacja w czasopiśmie

Typ:

artykuł w czasopiśmie wyróżnionym w JCR

Opublikowano w:

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES nr 19, wydanie 5, strony 1482 - 1505,
ISSN: 1661-6596

Język:

angielski

Rok wydania:

2018

Opis bibliograficzny:

Żołnowska B., Sławiński J., Brzozowski Z., Kawiak A., Belka M., Zielińska J., Bączek T., Chojnacki J.: Synthesis, Molecular Structure, Anticancer Activity, and QSAR Study of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)Benzenesulfonamide Derivatives// INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. -Vol. 19, iss. 5 (2018), s.1482-1505

DOI:

Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.3390/ijms19051482

Bibliografia: test

1. (C=N, C=C), 1342 (SO 2 asym ), 1158 (SO 2 sym ) cm −1 ; anal. C 47.04, H 3.29, N 18.29% calcd. for C 12 H 10 N 4 O 2 S 2 , C 46.77, H 2.96, N 17.91%.
2. General Procedures for the Synthesis of N-(aryl/heteroaryl)-4-(1-H-pyrrol-1-yl) otwiera się w nowej karcie
3. Benzenesulfonamides (23-40)
4. Method A. A mixture of 2,5-dimethoxytetrahydrofuran (198 mg, 1.5 mmol), p-dioxane (1.5 mL), glacial acetic acid (0.75 mL), and the corresponding 4-amino-N-(aryl/heteroaryl)benzenesulfonamide (13-19, I, II) (1.45 mmol) was stirred at reflux for 24 h. After cooling to room temperature, the mixture was evaporated in vacuum to dryness, and a residue was dissolved in boiling ethanol. After standing overnight, the precipitate was collected by filtration, washed with ethanol (2 × 2 mL), and dried at 105 • C. Method B. A mixture of 2,5-dimethoxytetrahydrofuran (198 mg, 1.5 mmol), p-dioxane (1 mL), glacial acetic acid (2 mL), and the corresponding 4-amino-N-(heteroaryl)benzenesulfonamide (20, 21, VII) (1.4 mmol) was stirred at reflux for 24 h. After cooling to room temperature and standing overnight, the precipitate was collected by filtration, washed successively with p-dioxane (3 × 1.5 mL), water (4 × 2 mL) and ethanol (3 × 1.5 mL), and dried at temperatures gradually increasing to 105 • C. Method C. A mixture of 2,5-dimethoxytetrahydrofuran (203 mg, 1.54 mmol), p-dioxane (2 mL), glacial acetic acid (1 mL), and the corresponding 4-amino-N-(heteroaryl)benzenesulfonamide (22, III-VI) (1.45 mmol) was stirred at reflux for 26 h. After cooling to room temperature and standing overnight, the precipitate was collected by filtration, washed successively with p-dioxane (2 × 2 mL), water (4 × 2 mL), and ethanol (3 × 3 mL), and dried at temperatures gradually increasing to 110 • C. otwiera się w nowej karcie
5. N-(4-Chlorophenyl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (23). A mixture of 2,5-dimethoxytetrahydrofuran (198 mg, 1.5 mmol), p-dioxane (1 mL), glacial acetic acid (2 mL), and 4-amino-N-(4-chlorophenyl)benzenesulfonamide 12 (410 mg, 1.4 mmol) was stirred at reflux for 24 h. After cooling to room temperature and standing overnight, the small amount (8 mg) of insoluble side products was filtered out, and the filtrate was concentrated in vacuum. To the residue water, 5 mL was added and stirred at room temperature for 6 h. The precipitate was collected by filtration, washed successively with water (6 × 1 mL) and ethanol (3 × 1 mL), and dried at temperatures gradually increasing to 105 • C. Yield for 23 (434 mg, 90%): m.p. 141-142 • C; IR (KBr) 3255 (NH), 1596 (NH def ), 1507, 1489, 1436 (C=N, C=C), 1333 (SO 2 asym ), 1157 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 6.30 (t, 2H, H-3 and H-4, pyrrole), 7.11 (d, J = 8.8 Hz, 2H, H-3 and H-5, 4-ClPh), 7.30 (d, J = 8.8 Hz, 2H, H-2 and H-6, 4-ClPh), 7.47 (t, 2H, H-2 and H-5, pyrrole), 7.77 (s, 4H, PhSO 2 ), 10.43 (s, 1H, SO 2 NH) ppm; 13 C NMR (125 MHz, DMSO-d 6 ) δ 112.4, 119.7, 119.8, 122.4, 129.0, 129.2, 129.9, 135.6, 137.4, 143.6 ppm; anal. C 57.74, H 3.93, N 8.41% calcd. for C 16 H 13 ClN 2 O 2 S, C 57.80, H 4.02, N 8.43%. otwiera się w nowej karcie
6. N-(2-(Phenylthio)phenyl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (24). Method A. Starting from 4-amino- N-[2-(phenylthio)phenyl]benzenesulfonamide 13 (517 mg), the title compound 24 was obtained (413 mg, 70%): m.p. 121.8-125.0 • C; IR (KBr) 3231 (NH), 1596 (NH def ), 1509, 1475, 1440 (C=N, C=C), 1337 (SO 2 asym ), 1168 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 6.32 (t, 2H, H-3 and H-4, pyrrole), 7.02-7.07 (m, 3H, arom.), 7.15-7.18 (m, 2H, arom.), 7.21-7.25 (m, 4H, arom.), 7.48 (t, 2H, H-2 and H-5, pyrrole), 7.73 (s, 4H, PhSO 2 ), 9.86 (s, 1H, SO 2 NH) ppm; anal. C 65.00, H 4.46, N 6.89% calcd. otwiera się w nowej karcie
7. N-(2-Phenoxyphenyl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (25). Method A. Starting from 4-amino- N-(2-phenoxyphenyl)benzenesulfonamide 14 (554 mg), the title compound 25 was obtained (396 mg, 70%): m.p. 146 • C; IR (KBr) 3309 (NH), 1598 (NH def ), 1510, 1491, 1421 (C=N, C=C), 1338 (SO 2 asym ), 1168 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 6.31 (t, 2H, H-3 and H-4, pyrrole), 6.63 (d, J = 7.8 Hz, 2H, arom.), 6.70 (d, J = 7.3 Hz, 1H, arom.), 7.00 (t, 1H, arom.), 7.06-7.13 (m, 2H, arom.), 7.19 (t, 2H, arom.), 7.40 (d, J = 7.3 Hz, 1H, arom.), 7.44 (t, 2H, H-2 and H-5, pyrrole), 7.66 (d, J = 8.8 Hz, 2H, PhSO 2 ), 7.72 (d, J = 8.8 Hz, 2H, PhSO 2 ), 9.96 (s, 1H, SO 2 NH); 13 C NMR (125 MHz, DMSO-d 6 ) otwiera się w nowej karcie
8. N-[2-(Phenylthio)pyridin-3-y]-4-(1H-pyrrol-1-yl)benzenesulfonamide (26). Method A. Starting from 4-amino-N-[2-(phenylthio)pyridin-3-y]benzenesulfonamide 15 (518 mg), the title compound 26 was obtained (236 mg, 40%): m.p. 113.4-113.8 • C; IR (KBr) 3253 (NH), 1598 (NH def ), 1510, 1475, 1439 (C=N, C=C), 1337 (SO 2 asym ), 1160 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 6.33 (t, 2H, H-3 and H-4, pyrrole), 7.15 (dd, J = 8.1, 4.7 Hz, 1H, arom.), 7.20 (d, J = 7.8 Hz, 2H, arom.), 7.27-7.32 (m, 3H, arom.), 7.39 (d, J = 8.3 Hz, 1H, arom.), 7.51 (t, 2H, H-2 and H-5, pyrrole), 7.76 (d, J = 8.8 Hz, 2H, PhSO 2 ), 7.81 (d, J = 8.8 Hz, 2H, PhSO 2 ), 8.17 (d, J = 4.9 Hz, 1H, arom.), 10.19 (s, 1H, SO 2 NH) ppm; anal. C 61.89, H 4.20, N 10.31% calcd. for C 21 H 17 N 3 O 2 S 2 , C 61.71, H 4.13, N 10.23%. otwiera się w nowej karcie
9. N-(2-Phenoxypyridin-3-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (27). otwiera się w nowej karcie
10. Method A. Starting from 4-amino-N-(2-phenoxypyridin-3-yl)benzenesulfonamide 16 (495 mg), the title compound 27 was obtained (369 mg, 65%): m.p. 163.7-165.8 • C; IR (KBr) 3295 (NH), 1598 (NH def ), 1512, 1489, 1451 (C=N, C=C), 1336 (SO 2 asym ), 1167 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 6.33 (t, 2H, H-3 and H-4, pyrrole), 6.72 (d, J = 7.8 Hz, 2H, arom.), 7.07-7.13 (m, 2H, arom.), 7.23 (t, 2H, arom.), 7.46 (t, 2H, H-2 and H-5, pyrrole), 7.73-7.80 (m, 5H, arom.), 7.86 (dd, J = 4.9, 1.5 Hz, 1H, arom.), 10.23 (s, 1H, SO 2 NH);
11. C NMR (125 MHz, DMSO-d 6 ) δ 112.1, 119.5, 119.6, 119.7, 121.6, 121.6, 124.9, 129.0, 129.7, 135.4, 136.4, 143.4, 144.2, 153.7, 156.7 ppm; anal. C 64.43, H 4.38, N 10.73% calcd. for C 21 H 17 N 3 O 3 S, C 64.09, H 4.41, N 10.66%. otwiera się w nowej karcie
12. -(1H-Pyrrol-1-yl)-N-(quinolin-8-yl)benzenesulfonamide (28). otwiera się w nowej karcie
13. Method A. Starting from 4-amino- N-(quinolin-8-yl)benzenesulfonamide 17 (434 mg), the title compound 28 was obtained (258 mg, 51%): m.p. 151.9-153.0 • C dec.; IR (KBr) 3254 (NH), 1597 (NH def ), 1505, 1471 (C=N, C=C), 1335 (SO 2 asym ), 1163 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 6.26 (t, 2H, H-3 and H-4, pyrrole), 7.41 (t, 2H, H-2 and H-5, pyrrole), 7.53 (t, 1H, arom.), 7.56 (dd, J = 8.3, 3.9 Hz, 1H, arom.), 7.66 (d, J = 8.3 Hz, 1H, arom.), 7.69 (d, J = 8.8 Hz, 2H, PhSO 2 ), 7.72 (d, J = 7.9 Hz, 1H, arom.), 7.96 (d, J = 8.8 Hz, 2H, PhSO 2 ), 8.33 (dd, J = 8.3, 2 Hz, 1H, arom.), 8.86 (dd, J = 4.4, 1.9 Hz, 1H, arom.), 10.06 (s, 1H, SO 2 NH); 13 C NMR (125 MHz, DMSO-d 6 ) δ 112.9, 117.3, 119.3, 119.5, 122.8, 123.6, 127.2, 128.6, 129.3, 134.1, 135.7, 136.0, 139.3, 143.4, 149.9 ppm; anal. C 65.31, H 4.33, N 12.03% calcd. for C 19 H 15 N 3 O 2 S, C 65.07, H 4.20, N 12.00%. otwiera się w nowej karcie
14. N-(2-Methylquinolin-8-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (29). otwiera się w nowej karcie
15. Method A. Starting from 4-amino-N-(2-methylquinolin-8-yl)benzenesulfonamide 18 (454 mg), the title compound 29 was obtained (316 mg, 60%): m.p. 167.6-168.7 • C; IR (KBr) 3225 (NH), 1596 (NH def ), 1506, 1472 (C=N, C=C), 1327 (SO 2 asym ), 1166 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 2.66 (s, 3H, CH 3 ), 6.27 (t, 2H, H-3 and H-4, pyrrole), 7.40-7.46 (m, 4H, arom. and H-2 and H-5, pyrrole), 7.60 (d, J = 7.8 Hz, 1H, arom.), 7.64 (d, J = 7.3 Hz, 1H, arom.), 7.69 (d, J = 8.8 Hz, 2H, PhSO 2 ), 7.94 (d, J = 8.8 Hz, 2H, PhSO 2 ), 8.20 (d, J = 8.8 Hz, 1H, arom.), 9.83 (s, 1H, SO 2 NH) ppm; anal. C 66.10, H 4.71, N 11.56% calcd. for C 20 H 17 N 3 O 2 S, C 66.02, H 4.69, N 11.56%. otwiera się w nowej karcie
16. N-(7-Methylquinolin-8-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (30). otwiera się w nowej karcie
17. Method A. Starting from 4-amino-N-(7-methylquinolin-8-yl)benzenesulfonamide 19 (454 mg), the title compound 30 was obtained (343 mg, 65%): m.p. 142-145 • C; IR (KBr) 3235 (NH), 1599 (NH def ), 1516, 1503, 1466 (C=N, C=C), 1335 (SO 2 asym ), 1167 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 2.59 (s, 3H, CH 3 ), 6.29 (t, 2H, H-3 and H-4, pyrrole), 7.29 (dd, J = 8.3, 3.9 Hz, 1H, arom.), 7.41 (t, 2H, H-2 and H-5, pyrrole), 7.53 (d, J = 8.3 Hz, 1H, arom.), 7.56 (br. s, 4H, arom.), 7.78 (d, J = 8.3 Hz, 1H, arom.), 8.21 (d, J = 8.3 Hz, 1H, arom.), 8.39 (d, J = 3.9 Hz, 1H, arom.), 9.74 (s, 1H, SO 2 NH); 13 C NMR (125 MHz, DMSO-d 6 ) δ 19.9, 111.9, 118.5, 119.5, 121.1, 127.0, 127.1, 129.3, 130.3, 131.5, 136.2, 137.3, 138.9, 142.5, 144.5, 149.7 ppm; anal. C 66.10, H 4.71, N 11.56% calcd. for C 20 H 17 N 3 O 2 S, C 65.82, H 4.68, N 11.51%. otwiera się w nowej karcie
18. N-(2-Methylquinolin-6-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (31). otwiera się w nowej karcie
19. Method B. Starting from 4-amino-N-(2-methylquinolin-6-yl)benzenesulfonamide 20 (439 mg), the title compound 31 was obtained (280 mg, 55%): m.p. 286-288 • C; IR (KBr) 3265, 3140 (SO 2 NH), 1596 (NH def ), 1510, 1475 (C=N, C=C), 1340 (SO 2 asym ), 1160 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 2.57 (s, 3H, CH 3 ), 6.26 (br. s, 2H, H-3 and H-4, pyrrole), 7.33 (d, J = 6.8 Hz, 1H, H-3, quinoline), 7.42-7.46 (m, 3H, arom.), 7.59 (s, 1H, H-5, quinoline), 7.73-7.96 (m, 5H, arom.), 8.14 (d, J = 6.4 Hz, 1H, H-8, quinoline), 10.58 (s, 1H, SO 2 NH) ppm; 13 C NMR (125 MHz, DMSO-d 6 ) δ 24.7, 111,9, 116.3, 119.3, 122.9, 124.0, 126.7, 128.8, 129.6, 135.4, 143.1, 144.7, 158.0 ppm; anal. C 66.09, H 4.71, N 11.56% calcd. for C 20 H 17 N 3 O 2 S, C 66.12, H 4.81, N 11.55%. otwiera się w nowej karcie
20. -(1H-pyrrol-1-yl)-N-(4H-1,2,4-triazol-4-yl)benzenesulfonamide (32). otwiera się w nowej karcie
21. Method B. Starting from 4-amino-N-(4H-1,2,4-triazol-4-yl)benzenesulfonamide 21 (335 mg), the title compound 32 was obtained (219 mg, 54%): m.p. 251-252 • C dec.; IR (KBr) 3150 (NH), 1595 (NH def ), 1515, 1475, 1425 (C=N, C=C), 1340 (SO 2 asym ), 1165 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 6.35 (br. s, 2H, H-3 and H-4, pyrrole), 7.57 (br. s, 2H, H-2 and H-5, pyrrole), 7.70 (d, J = 8.3 Hz, 2H, H-3 and H-5, PhSO 2 ), 7.88 (d, J = 8.3 Hz, 2H, H-2 and H-6, PhSO 2 ), 8.37 (s, 2H, H-3 and H-5, 1,2,4-triazole), 11.90 (br. s, 1H, SO 2 NH) ppm; 13 C NMR (DMSO-d 6 ) δ 112.7, 119.9, 120.0, 130.4, 143.5, 144.7 ppm; anal. C 49.82, H 3.83, N 24.20% calcd. for C 12 H 11 N 5 O 2 S, C 49.80, H 3.93, N 24.19%.
22. N-(Benzo-2,1,3-thiadiazol-4-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (33). Method C. Starting from 4-amino-N-(benzo-2,1,3-thiadiazol-4-yl)benzenesulfonamide 22 (444 mg), the title compound 33 was obtained (336 mg, 65%): m.p. 325-327 • C dec.; IR (KBr) 3320, 3225 (NH), 1595 (NH def ), 1540, 1510, 1495 (C=N, C=C), 1340 (SO 2 asym ), 1170 (SO 2 sym ) cm −1 ; 1 H NMR (220 MHz, DMSO-d 6 ) δ 6.30 (br. s, 2H, H-3 and H-4, pyrrole), 7.46 (br. s, 2H, H-2 and H-5, pyrrole), 7.64 (t, J = 7.8 Hz, 1H, H-6, benzothiadizole), 7.68-7.80 (m, 4H, H-3 and H-5, PhSO 2 and H-5 and H-7 benzothiadiazole), 7.90 (d, J = 8.0 Hz, 2H, H-2 and H-6 PhSO 2 ), 11.0 (br. s, 1H, SO 2 NH) ppm; 13 C NMR (DMSO-d 6 ) δ 111.9, 117.2, 118.1, 119.2, 119.4, 129.0, 129.7, 130.7, 136.0, 143.2, 149.0, 155.1 ppm; anal. C 53.91, H 3.39, N 15.72% calcd. for C 16 H 12 N 4 O 2 S 2 , C 54.02, H 3.48, N 15.81%. otwiera się w nowej karcie
23. N-(5-Methylisoxazol-3-yl)-4-(1H-pyrrol-1-yl)-benzenesulfonamide (34). otwiera się w nowej karcie
24. Method A. Starting from 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide I (367 mg), the title compound 34 was obtained (387 mg, 88%): m.p. 203-204.8 • C; IR (KBr) 3235 (NH), 1599 (NH def ), 1516, 1503, 1466 (C=N, C=C), 1337 (SO 2 asym ), 1168 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 2.29 (s, 3H, CH 3 ), 6.17 (s, 1H, arom.), 6.32 (s, 2H, H-3 and H-4, pyrrole), 7.49 (s, 2H, H-2 and H-5, pyrrole), 7.82 (d, J = 8.8 Hz, 2H, H-2 and H-6 PhSO 2 ), 7.89 (d, J = 8.8 Hz, 2H, H-2 and H-6 PhSO 2 .), 11.46 (s, 1H, SO 2 NH); 13 C NMR
25. MHz, DMSO-d 6 ) δ 12.7, 96.1, 112.4, 119.8, 119.9, 129.3, 135.9, 143.9, 158.2, 171.2 ppm; anal. C 55.43, H 4.32, N 13.85% calcd. for C 14 H 13 N 3 O 3 S, C 54.96, H 4.24, N 13.75%.
26. N-(Pyridin-2-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (35). Method A. Starting from 4-amino-N- (pyridin-2-yl)benzenesulfonamide II (361 mg), the title compound 35 was obtained (391 mg, 90%): m.p. 244-246.4 • C; IR (KBr) 3138 (NH), 1634 (NH def ), 1535, 1512, 1466 (C=N, C=C), 1359 (SO 2 asym ), 1142 (SO 2 sym ) cm −1 ; 1 H NMR (500 MHz, DMSO-d 6 ) δ 6.29 (s, 2H, H-3 and H-4, pyrrole), 6.86 (t, 1H, arom.), 7.17 (d, 1H, arom.), 7.45 (s, 2H, H-2 and H-5, pyrrole), 7.71 (d, 1H, arom.), 7.74 (d, J = 8.8 Hz, 2H, H-2 and H-6 PhSO 2 ), 7.90 (d, J = 8.8 Hz, 2H, H-2 and H-6 PhSO 2 .), 8.00 (d, 1H, arom.), 12.06 (s, 1H, SO 2 NH); 13 C NMR (125 MHz, DMSO-d 6 ) δ 112.2, 114.6, 116.1, 119.6, 119.8, 129.0, 138.8, 141.4, 143.0, 153.9 ppm; anal. C 60.18, H 4.38, N 14.04% calcd. for C 15 H 13 N 3 O 2 S, C 60.00, H 4.19, N 13.88%. N-(Pyrimidin-2-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (36). Method C. Starting from 4-amino-N -(pyrimidin-2-yl)benzenesulfonamide III (363 mg), the title compound 36 was obtained (379 mg, 87%): m.p. 260-261 • C dec.; IR (KBr) 3150 (NH), 1600 (NH def ), 1585, 1510, 1445 (C=N, C=C), 1345 otwiera się w nowej karcie
27. (SO 2 asym ), 1160 (SO 2 sym ) cm −1 ; 1 H NMR (200 MHz, DMSO-d 6 ) δ 6.30 (br. s, 2H, H-3 and H-4, pyrrole), 7.04 (t, J = 4.9 Hz, 1H, H-5, pyrimidine), 7.48 (br. s, 2H, H-2 and H-5, pyrrole), 7.85 (d, J = 8.8 Hz, 2H, H-3 and H-5, PhSO 2 ), 8.01 (d, J = 8.8 Hz, 2H, H-2 and H-6, PhSO 2 ), 8.50 (d, J = 4.9 Hz, 2H, H-4 and H-6, (pyrimidine), 11.88 (br. s, 1H, SO 2 NH) ppm; 13 C NMR (50 MHz, DMSO-d 6 ) δ 112.3, 119.4, 119.8, 130.1, 136.9, 143.5, 157.5, 159.0 ppm; anal. C 55.99, H 4.02, N 18.65% calcd. for C 14 H 12 N 4 O 2 S, C 56.20, H 4.22, N 18.72%. otwiera się w nowej karcie
28. N-(4-Methylpyrimidin-2-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (37). otwiera się w nowej karcie
29. Method C. Starting from 4-amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamide IV (383 mg) the title compound 37 was obtained (392 mg, 86%): m.p. 256-257 • C dec.; IR (KBr) 3235 (NH), 1600 (NH def ), 1565, 1510, 1405 (C=N, C=C), 1345 (SO 2 asym ), 1150 (SO 2 sym ) cm −1 ; 1 H NMR (200 MHz, DMSO-d 6 ) δ 2.31 (s, 3H CH 3 ), 6.30 (br. s, 2H, H-3 and H-4, pyrrole), 6.90 (d, J = 4.9 Hz, 1H, H-5, pyrimidine), 7.47 (br. s, 2H, H-2 and H-5, pyrrole), 7.77 (d, J = 8.3 Hz, 2H, H-3 and H-5, PhSO 2 ), 8.01 (d, J = 8.3 Hz, 2H, H-2 and H-6, PhSO 2 ), 8.32 (d, J = 4.9 Hz, 1H, H-6, pyrimidine), 11.82 (br. s, 1H, SO 2 NH) ppm; 13 C NMR (50 MHz, DMSO-d 6 ) δ 23.9, 112.3, 119.2, 119.8, 130.3, 137.2, 143.4, 157.2 ppm; anal. C 57.31, H 4.49, N 17.82% otwiera się w nowej karcie
30. N-(4,6-Dimethylpyrimidin-2-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (38). Method C. Starting from 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide V (404 mg), the title compound 38 was obtained (376 mg, 79%): m.p. 224-227 • C dec.; IR (KBr) 3245 (NH), 1600 (NH def ), 1585, 1510, 1475 (C=N, C=C), 1335 (SO 2 asym ), 1160 (SO 2 sym ) cm −1 ; 1 H NMR (200 MHz, DMSO-d 6 ) δ 2.24 (s, 6H, 2 × CH 3 ), 6.29 (br. s, 2H, H-3 and H-4, pyrrole), 6.74 (s, 1H, H-5, pyrimidine), 7.46 (br. s, 2H, H-2 and H-5, pyrrole), 7.76 (d, J = 8.3 Hz, 2H, H-3 and H-5, PhSO 2 ), 8.02 (d, J = 8.3 Hz, 2H, H-2 and H-6, PhSO 2 ), 11.86 (br. s, 1H, SO 2 NH) ppm; 13 C NMR (50 MHz, DMSO-d 6 ) δ 23.5, 112.2, 119.0, 119.8, 130.5, 143.2, 156.8 ppm; anal. C 58.51, H 4.91, N 17.06% calcd. for C 16 H 16 N 4 O 2 S, C 58.85, H 5.30, N 17.52%. N-(2,6-Dimethoxypirimidin-4-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (39). Method C. Starting from 4-amino-N-(2,6-dimethoxypirimidin-4-yl)benzenesulfonamide VI (450 mg) the title compound 39 was obtained (423 mg, 81%): m.p. 162-163 • C dec.; IR (KBr) 3240, 3150 (NH), 1595 (NH def ), 1510, 1490, 1455 (C=N, C=C), 1335 (SO 2 asym ), 1160 (SO 2 sym ) cm −1 ; 1 H NMR (200 MHz, DMSO-d 6 ) δ 3.78 (s, 3H CH 3 O, pyrimidine), 3.81 (s, 3H, CH 3 O-2, pyrimidine), 5.99 (s, 1H, H-5, pyrimidine), 6.34 (br. s, 2H, H-3 and H-4, pyrrole), 7.51 (br. s, 2H, H-2 and H-5, pyrrole), 7.84 (d, J = 8.4 Hz, 2H, H-3 and H-5, PhSO 2 ), 8.00 (d, J = 8.4 Hz, 2H, H-2 and H-6, PhSO 2 ), 11.86 (br. s, 1H, SO 2 NH) ppm; 13 C NMR otwiera się w nowej karcie
31. MHz, DMSO-d 6 ) δ 54.1, 54.8, 85.0, 112.0, 119.3, 119.5, 129.3, 136.0, 143.4, 160.1, 164.2, 171.9 ppm; anal. C 53.32, H 4.47, N 15.54% calcd. for C 16 H 16 N 4 O 4 S, C 53.48, H 4.60, N 15.70%. otwiera się w nowej karcie
32. N-(6-Methoxypyridazin-3-yl)-4-(1H-pyrrol-1-yl)benzenesulfonamide (40). otwiera się w nowej karcie
33. Method B. Starting from 4-amino-N-(6-methoxypyridazin-3-yl)benzenesulfonamide VII (392 mg), the title compound 40 was obtained (241 mg, 52%): 191-192 • C; IR (KBr) 3215 (NH), 1645 (NH def ), 1525, 1510, 1470 (C=N, C=C), 1335 (SO 2 asym ), 1145 (SO 2 sym ) cm −1 ; 1 H NMR (200 MHz, DMSO-d 6 ) δ 3.83 (s, 3H, CH 3 O), 6.30 (br. s, 2H, H-3 and H-4, pyrrole), 7.37 (d, J = 7.9 Hz, 1H, H-5, pyridazine), 7.48 (br. s, 2H, H-2 and H-5, pyrrole), 7.72-7.81 (m, 3H, H-3 and H-5, PhSO 2 , and H-4, pyridazine), 7.87 (d, J = 8.6 Hz, 2H, H-2 and H-6, PhSO 2 ), 13.00 (br. s, 1H, SO 2 NH) ppm; 13 C NMR (50 MHz, DMSO-d 6 ) δ 53.54, 110.9, 117.8, 118.5, 119.2, 125.0, 128.2, 140.5, 144.3, 158.7, 159.9 ppm; anal. C 54.53, H 4.27, N 16.96% calcd. for C 15 H 14 N 4 O 3 S, C 54.52, H 4.30, N 16.95%. otwiera się w nowej karcie
34. X-ray Structure Determination X-Ray diffraction data were collected on the IPDS 2T dual-beam diffractometer (STOE & Cie GmbH, Darmstadt, Germany) at 120.0(2) K with Cu-Kα radiation of a microfocus X-ray source (GeniX 3D Cu High Flux, Xenocs, Sassenage, France, 50 kV, 0.6 mA, λ = 154.186 pm). During the experiment, the crystal was kept in nitrogen stream at 120 K using CryoStream-800 device (Oxford CryoSystem, Oxford, UK). Control of data collection and data reduction was performed by X-Area 1.75 otwiera się w nowej karcie
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