Int. J. Mol. Sci. 2020, 21, 2560
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18. 4-(3-(2-(([1,10-biphenyl]-4-ylmethyl)amino)ethyl)ureido) benzenesulfonamide (25): White
solid, yield 37%; mp 197–198 ◦C; TLC Rf 0.13 (MeOH/DCM 10% v/v); δH (400 MHz, DMSO-d6) 2.66
(2H, t, J 6.1), 3.24 (2H, q, J 6.1), 3.79 (2H, brs), 6.41 (1H, brt, J 6.1, exchange with D2O, NH), 7.18 (2H, s,
exchange with D2O, SO2NH2), 7.38 (1H, t, J 7.4), 7.49 (4H, m), 7.56 (2H, d, J 8.8), 7.63-7.70 (6H, m), 9.07
(1H, s, exchange with D2O, NH); δC (100 MHz, DMSO-d6) 39.6, 49.3, 53.3, 117.7, 127.4, 127.5, 127.7,
128.2, 129.5, 129.8, 136.9, 139.4, 141.0, 141.1, 144.7, 155.9; m/z (ESI positive) 425.1 [M+H]+.
19. 3-(3-(2-(benzylamino)ethyl)ureido)benzenesulfonamide (26): Pale yellow solid, yield 16%; mp
109–110 ◦C; TLC Rf 0.12 (MeOH/DCM 10% v/v); δH (400 MHz, DMSO-d6) 2.63 (2H, t, J 6), 3.22 (2H,
q, J 6), 3.75 (2H, brs), 6.29 (1H, t, J 6, exchange with D2O, NH), 7.25 (1H, t, J 7), 7.32-7.44 (8H, m, 2H
exchange with D2O, SO2NH2), 7.54 (1H, d, J 7.9), 8.00 (1H, brt, J 1.6), 8.97 (1H, s, exchange with D2O,
NH); δC (100 MHz, DMSO-d6) 39.8, 49.3, 53.6, 115.3, 118.8, 121.2, 127.5, 128.9, 129.0, 130.1, 141.7, 142.0,
145.5, 156.0; m/z (ESI positive) 349.1 [M+H]+.
20. 3-(3-(2-((4-chlorobenzyl)amino)ethyl)ureido) benzenesulfonamide (27): Pale yellow solid,
yield 10%; mp 102–103 ◦C; TLC Rf 0.11 (MeOH/DCM 10% v/v); δH (400 MHz, DMSO-d6) 2.67 (2H, t, J
6), 3.24 (2H, q, J 6), 3.79 (2H, brs), 6.32 (1H, t, J 6, exchange with D2O, NH), 7.32 (2H, s, exchange with
D2O, SO2NH2), 7.36-7.44 (6H, m), 7.54 (1H, d, J 7.8), 8.00 (1H, s), 8.98 (1H, s, exchange with D2O, NH);
δC (100 MHz, DMSO-d6) 39.7, 49.2, 52.5, 115.5, 119.0, 121.4, 129.1, 130.2, 131.0, 132.4, 139.8, 142.0, 145.6,
156.2; m/z (ESI positive) 383.1 [M+H]+.
21. 3-(3-(2-((4-fluorobenzyl)amino)ethyl)ureido) benzenesulfonamide (28): Pale yellow solid,
yield 35%; mp 104–105 ◦C; TLC Rf 0.11 (MeOH/DCM 10% v/v); δH (400 MHz, DMSO-d6) 2.68 (2H, t,
J 6), 3.25 (2H, q, J 6), 3.80 (2H, brs), 6.38 (1H, t, J 6, exchange with D2O, NH), 7.18 (2H, m), 7.33 (2H,
s, exchange with D2O, SO2NH2), 7.37-7.47 (4H, m), 7.55 (1H, d, J 8.0), 8.02 (1H, d, J 1.8), 9.05 (1H, s,
exchange with D2O, NH); δC (100 MHz, DMSO-d6) 39.6, 49.1, 52.4, 115.4, 115.8 (d, 2JC-F 23), 118.9, 121.3,
130.2, 131.1 (d, 3JC-F 8), 136.8, 142.0, 145.5, 156.1, 162.2 (d, 1JC-F 240); δF (376 MHz, DMSO-d6) -116.1 (1F,
s); m/z (ESI positive) 367.1 [M+H]+.
22. 3-(3-(2-((2-fluorobenzyl)amino)ethyl)ureido) benzenesulfonamide (29): Pale yellow solid,
yield 15%; mp 155–156 ◦C; TLC Rf 0.12 (MeOH/DCM 10% v/v); δH (400 MHz, DMSO-d6) 2.72 (2H, t, J
6), 3.27 (2H, q, J 6), 3.87 (2H, brs), 6.34 (1H, t, J 6, exchange with D2O, NH), 7.22 (2H, m), 7.32 (2H, s,
exchange with D2O, SO2NH2), 7.34-7.45 (3H, m), 7.55 (2H, m), 8.01 (1H, brt, J 1.8), 9.00 (1H, s, exchange
with D2O, NH); δC (100 MHz, DMSO-d6) 39.5, 46.2 (d, J 3.4), 49.2, 115.5, 116.0 (d, J 22), 119.0, 121.4,
125.3 (d, JC-F 3.6), 126.9 (d, J 14.7), 130.1 (d, J 8), 130.2, 131.7 (d, J 5), 142.0, 145.5, 156.2, 161.3 (d, J 243); δF
(395 MHz, DMSO-d6) -118.7 (1F, s); m/z (ESI positive) 367.1 [M+H]+.
23. 3-(3-(2-((4-hydroxybenzyl)amino)ethyl)ureido) benzenesulfonamide (30): Orange solid, yield
15%; mp 133–134 ◦C; TLC Rf 0.10 (MeOH/DCM 10% v/v); δH (400 MHz, DMSO-d6) 2.59 (2H, t, J 6), 3.20
(2H, q, J 6), 3.61 (2H, brs), 6.36 (1H, brt, J 6, exchange with D2O, NH), 6.72 (2H, d, J 8.4), 7.15 (2H, d, J
8.4), 7.34-7.44 (3H, m, 2H exchange with D2O, SO2NH2), 7.42 (1H, t, J 7.9), 7.53 (1H, d, J 7.9), 8.01 (1H,
brt, J 1.8), 9.06 (1H, s, exchange with D2O, NH), 9.27 (1H, s, exchange with D2O, OH); δC (100 MHz,
DMSO-d6) 39.2, 49.5, 53.5, 116.5, 116.7, 120.3, 123.0, 131.3, 132.0, 142.2, 145.6, 157.3, 157.4; m/z (ESI
positive) 365.1 [M+H]+.
24. 3-(3-(2-((4-nitrobenzyl)amino)ethyl)ureido) benzenesulfonamide (31): Pale yellow solid,
yield 10%; mp 109–110 ◦C; TLC Rf 0.11 (MeOH/DCM 10% v/v); δH (400 MHz, DMSO-d6) 2.62 (2H, t, J
6), 3.24 (2H, q, J 6), 3.91 (2H, brs), 6.33 (1H, t, J 6, exchange with D2O, NH), 7.33-7.45 (4H, m, 2H, s,
exchange with D2O, SO2NH2), 7.54 (1H, d, J 8.0), 7.68 (2H, d, J 8.6), 8.01 (1H, t, J 2), 8.23 (2H, d, J 8.6),
8.99 (1H, s, exchange with D2O, NH); δC (100 MHz, DMSO-d6) 39.8, 49.4, 52.8, 115.6, 119.3, 121.7, 124.5,
130.3, 130.5, 142.0, 145.5. 147.6, 149.9, 156.3; m/z (ESI positive) 394.0 [M+H]+.
25. 3-(3-(2-((4-(dimethylamino)benzyl)amino)ethyl)ureido) benzenesulfonamide (32): Pale brown
solid, yield 10%; mp 101–103 ◦C; TLC Rf 0.13 (MeOH/DCM 10% v/v); δH (400 MHz, DMSO-d6) 2.64
(2H, t, J 5.8), 2.89 (6H, s), 3.23 (2H, q, J 5.8), 3.66 (2H, brs), 6.31 (1H, t, J 5.8, exchange with D2O, NH),
6.71 (2H, d, J 8.6), 7.19 (2H, d, J 8.6), 7.32-7.38 (3H, m, 2H exchange with D2O, SO2NH2), 7.43 (1H, t, J
7.8), 7.54 (1H, d, J 7.8), 8.00 (1H, t, J 1.8), 9.00 (1H, s, exchange with D2O, NH); δC (100 MHz, DMSO-d6)