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3.5.23. N-(4-(bis(5-bromo-1H-indol-3-yl)methyl)phenyl)-4-chloro-3-
nitrobenzene sulfonamide (4h)
(d, J = 2.0 Hz, 2H), 6.79 (d, J = 1.6 Hz, 1H), 5.78 (s, 1H), 5.74 (s,
1H); 13C NMR (125 MHz, MeOD-d4): d 141.19, 140.16, 138.22,
138.22, 136.42, 135.54, 129.43, 129.43, 129.02, 129.02, 128.42,
128.42, 126.78, 126.78, 125.71, 125.71, 125.21, 125.21, 123.81,
123.81, 117.98, 117.98, 116.71, 116.71, 114.03, 114.03, 110.11,
Brown solid; Yield 78.3%; m.p. 238–240 °C; 1H NMR (300 MHz,
DMSO-d6): d 11.03 (s, 2H), 10.44 (s, 1H), 8.37 (s, 1H), 7.91 (s, 1H),
7.32 (d, J = 11.7 Hz, 2H), 7.29 (d, J = 8.4 Hz, 2H), 7.20 (d,
J = 8.4 Hz, 1H), 7.11 (d, J = 8.7 Hz, 2H), 7.03 (d, J = 8.4 Hz, 1H),
6.97 (t, J = 8.1 Hz, 1H), 6.80 (d, J = 1.5 Hz, 2H), 6.49 (d, J = 8.1 Hz,
1H), 5.77 (s, 1H), 5.62 (s, 1H); 13C NMR (125 MHz, MeOD-d4): d
146.52, 140.73, 139.17, 139.17, 136.43, 135.64, 135.45, 132.86,
128.31, 128.31, 127.68, 127.68, 125.81, 125.81, 125.39, 125.39,
124.08, 124.08, 123.81, 123.81, 117.85, 117.85, 116.87, 116.87,
114.16, 114.16, 110.26, 110.26, 37.26; Anal. Calcd for C29H19Br2
ClN4O4S: C = 48.73; H, 2.68; N, 7.84; Found: C = 48.74; H, 2.69;
N = 7.86; EI MS m/z (% rel. abund.): 714.1 (M+, 34.2%), 714.3 (M
+2, 12.6%).
110.11, 37.51; Anal. Calcd for
C29H20Br2ClN3O2S: C = 52.00;
H = 3.01; N = 6.27; Found: C = 52.01; H = 3.02; N = 6.29; EI MS m/
z (% rel. abund.): 669.1 (M+, 57.2%), 671.1 (M+2, 19.9%).
3.5.28. N-(4-(bis(5-bromo-1H-indol-3-yl)methyl)phenyl)-5-
(dimethylamino) naphthalene-1-sulfonamide (4m)
Yellow solid; Yield 83.7%; m.p. 267–268 °C; 1H NMR (300 MHz,
DMSO-d6): d 10.99 (s, 2H), 10.43 (s, 1H), 8.42 (d, J = 8.7 Hz, 1H),
8.30 (d, J = 8.4 Hz, 1H), 8.12 (d, J = 7.2 Hz, 1H), 7.57 (d, J = 7.2 Hz,
1H), 7.51 (d, J = 7.5 Hz, 1H), 7.30 (s, 3H), 7.27 (m, 1H), 7.21 (d,
J = 7.2 Hz, 1H), 7.10 (dd, J = 6.3 Hz, 2H), 7.08 (d, J = 6.9 Hz, 2H),
6.91 (d, J = 8.4 Hz, 2H), 6.73 (d, J = 1.8 Hz, 2H), 5.68 (s, 1H), 2.80
(s, 6H); 13C NMR (125 MHz, MeOD-d4): d 144.49, 139.19, 139.19,
136.52, 135.67, 135.28, 132.89, 131.81, 128.92, 128.64, 128.11,
128.11, 127.65, 127.65, 125.41, 125.41, 125.13, 125.13, 124.61,
124.61, 123.84, 123.42, 117.68, 117.68, 116.95, 116.95, 116.67,
114.13, 114.13, 112.86, 109.82, 109.82, 41.68, 41.68, 37.40; Anal.
Calcd for C35H28Br2N4O2S: C = 57.70; H = 3.87; N = 7.69; Found:
C = 57.68; H = 3.89; N = 7.71; EI MS m/z (% rel. abund.): 728.1
(M+, 62.8%).
3.5.24. N-(4-(bis(5-bromo-1H-indol-3-yl)methyl)phenyl)-2-methyl-5-
nitrobenzenesulfonamide (4i)
Yellow solid; Yield 74.4%; m.p. 251–253 °C; 1H NMR (300 MHz,
DMSO-d6): d 11.03 (s, 2H), 10.55 (s, 1H), 8.54 (d, J = 2.4 Hz, 1H),
8.30 (dd, J = 2.1 Hz, 8.1 Hz, 1H), 7.63 (d, J = 8.4 Hz, 1H), 7.31 (s,
2H), 7.28 (d, J = 8.7 Hz, 2H), 7.17 (d, J = 8.4 Hz, 2H), 7.11 (dd,
J = 1.8 Hz, 8.4 Hz, 2H), 6.97 (d, J = 8.4 Hz, 2H), 6.76 (d, J = 2.1 Hz,
2H), 5.74 (s, 1H), 2.60 (s, 3H); 13C NMR (125 MHz, MeOD-d4): d
144.72, 143.51, 139.58, 139.58, 138.12, 136.17, 135.59, 132.12,
128.59, 128.59, 127.89, 127.89, 126.38, 125.85, 125.85, 125.27,
125.27, 123.76, 123.76, 122.47, 117.82, 117.82, 116.51, 116.51,
114.13, 114.13, 110.29, 110.29, 37.24, 20.69; Anal. Calcd for C30
H22Br2N4O4S: C = 51.89; H = 3.19; N = 8.07; Found: C = 51.89;
H = 3.19; N = 8.07; EI MS m/z (% rel. abund.): 693.0 (M+, 44.5%).
3.5.29. N-(4-(bis(5-bromo-1H-indol-3-yl)methyl)phenyl)butane-1-
sulfonamide (4n)
Brown solid; Yield 87.2%; m.p. 237–239 °C; 1H NMR (400 MHz,
DMSO-d6): d 11.05 (s, 2H), 9.65 (s, 1H), 7.39 (d, J = 1.6 Hz, 2H), 7.31
(d, J = 8.4 Hz, 2H), 7.27 (d, J = 8.8 Hz, 2H), 7.14 (dd, J = 8.0 Hz, 1.6 Hz,
2H), 7.11 (d, J = 8.0 Hz, 2H), 6.87 (d, J = 2.0 Hz, 2H), 5.80 (s, 1H), 3.01
(t, J = 7.6, 2H), 1.60 (q, J = 8.0 Hz, 2H), 1.31 (sextet, J = 7.2 Hz, 2H),
0.79 (t, J = 7.6 Hz, 3H); 13C NMR (125 MHz, MeOD-d4): d 139.17,
139.17, 136.93, 135.71, 127.73, 127.73, 126.92, 126.92, 125.76,
125.76, 123.89, 123.89, 123.36, 123.36, 117.81, 117.81, 116.76,
116.76, 114.04, 114.04, 110.12, 110.12, 52.60, 37.30, 26.65, 21.00,
3.5.25. N-(4-(bis(5-bromo-1H-indol-3-yl)methyl)phenyl)-5-bromo-2-
methoxybenzene sulfonamide (4j)
Orange solid; Yield 63.5%; m.p. 246–248 °C; 1H NMR (300 MHz,
DMSO-d6): d 11.03 (s, 2H), 9.99 (s, 1H), 7.69–7.79 (m, 3H), 7.32 (d,
J = 1.8 Hz, 2H), 7.28 (d, J = 8.7 Hz, 2H), 7.10–7.17 (m, 4H), 6.97 (d,
J = 8.4 Hz, 2H), 6.76 (d, J = 1.8 Hz, 2H), 5.73 (s, 1H), 3.80 (s, 3H); 13
C
NMR (125 MHz, MeOD-d4): d 160.73, 138.12, 138.12, 135.47,
134.91, 134.68, 133.78, 128.62, 128.62, 127.71, 127.71, 126.18,
125.61, 125.61, 125.36, 125.36, 123.82, 123.82, 117.76, 117.76,
116.85, 116.85, 115.28, 114.01, 114.01, 112.37, 110.26, 110.26,
56.74, 37.45; Anal. Calcd for C30H22Br3N3O3S: C = 48.41; H = 2.98;
N = 5.65; Found: C = 48.42; H = 2.97; N = 5.66; EI MS m/z (% rel.
abund.): 745.1 (M+, 92.6%).
14.01; Anal. Calcd for C27H25Br2N3O2S: C = 52.70; H = 4.09;
N = 6.83; Found: C = 52.71; H = 4.11; N = 6.81; EI MS m/z (% rel.
abund.): 615.1 (M+, 39.6%).
3.5.30. N-(4-(bis(5-bromo-1H-indol-3-yl)methyl)phenyl)methane
sulfonamide (4o)
Red solid; Yield 72.9%; m.p. 219–221 °C; 1H NMR (300 MHz,
DMSO-d6): d 11.04 (s, 2H), 9.58 (s, 1H), 7.40 (d, J = 1.2 Hz, 2H),
7.32 (d, J = 8.7 Hz, 2H), 7.28 (d, J = 9.6 Hz, 2H), 7.11–7.15 (m,
4H), 6.88 (d, J = 1.8 Hz, 2H), 5.81 (s, 1H), 2.94 (s, 3H); 13C NMR
(125 MHz, MeOD-d4): d 139.17, 139.17, 137.61, 135.21, 127.83,
127.83, 126.17, 126.17, 125.76, 125.76, 123.81, 123.81, 122.39,
122.39, 117.78, 117.78, 116.81, 116.81, 114.15, 114.15, 110.18,
110.18, 42.15, 37.35; Anal. Calcd for C24H19Br2N3O2S: C = 50.28;
H = 3.34; N = 7.33; Found: C = 50.29; H = 3.32; N = 7.34; EI MS
m/z (% rel. abund.): 573.2 (M+, 49.3%).
3.5.26. N-(4-(bis(5-bromo-1H-indol-3-yl)methyl)phenyl)-3,5-
dichloro-2-hydroxybenzene sulfonamide (4k)
Orange solid; Yield 89.2%; m.p. 238–240 °C; 1H NMR (300 MHz,
DMSO-d6): d 11.03 (s, 2H), 10.10 (s, 1H), 7.78 (d, J = 2.4 Hz, 1H),
7.55 (d, J = 2.7 Hz, 1H), 7.33 (d, J = 5.1 Hz, 2H), 7.29 (d, J = 8.7 Hz,
2H), 7.17 (d, J = 9.0 Hz, 2H), 7.12 (d, J = 8.7 Hz, 2H), 7.10 (d,
J = 8.7 Hz, 2H), 7.00 (d, J = 8.4 Hz, 1H), 6.76 (s, 2H), 5.74 (s, 1H);
13C NMR (125 MHz, MeOD-d4): d 157.17, 139.12, 139.12, 136.47,
135.58, 134.14, 128.60, 128.60, 128.21, 127.78, 127.78, 127.40,
125.81, 125.81, 125.31, 125.31, 124.20, 123.86, 123.86, 121.39,
117.88, 117.88, 116.91, 116.91, 114.06, 114.06, 110.16, 110.16,
37.30; Anal. Calcd for C29H19Br2Cl2N3O3S: C = 48.36; H = 2.66;
N = 5.83; Found: C = 48.37; H = 2.64; N = 5.81; EI MS m/z (% rel.
abund.): 720.2 (M+, 38.5%), 722.3 (M+2, 14.3%).
3.5.31. N-(4-(bis(5-chloro-1H-indol-3-yl)methyl)phenyl)benzene
sulfonamide (5a)
Orange solid; Yield 79.3%; m.p. 223–225 °C; 1H NMR (400 MHz,
DMSO-d6): d 11.02 (s, 2H), 10.10 (s, 1H), 7.68 (d, J = 7.6 Hz, 2H),
7.57 (t, J = 7.2 Hz, 1H), 7.49 (t, J = 7.2 Hz, 2H), 7.34 (d, J = 8.8 Hz,
2H), 7.17 (s, 2H), 7.15 (d, J = 9.6 Hz, 2H), 7.02 (dd, J = 1.6 Hz,
8.4 Hz, 2H), 6.98 (d, J = 8.4 Hz, 2H), 6.79 (d, J = 2.0 Hz, 2H), 5.72
(s, 1H); 13C NMR (125 MHz, MeOD-d4): d 140.65, 137.93, 137.93,
136.37, 135.48, 134.09, 128.81, 128.81, 128.34, 128.34, 127.84,
127.84, 127.49, 127.49, 127.18, 127.18, 125.21, 125.21, 123.38,
123.38, 120.71, 120.71, 117.72, 117.72, 114.84, 114.84, 110.12,
3.5.27. N-(4-(bis(5-bromo-1H-indol-3-yl)methyl)phenyl)-4-
chlorobenzene sulfonamide (4l)
White solid; Yield 86.1%; m.p. 264–266 °C; 1H NMR (400 MHz,
DMSO-d6): d 11.04 (s, 2H), 10.19 (s, 1H), 7.67 (d, J = 8.4 Hz, 1H),
7.56 (d, J = 8.4 Hz, 1H), 7.39 (s, 1H), 7.32 (s, 2H), 7.30 (d,
J = 8.8 Hz, 1H), 7.13–7.21 (m, 5H), 6.97 (d, J = 8.4 Hz, 1H), 6.86
110.12, 37.41; Anal. Calcd for
C29H21Cl2N3O2S: C = 63.74;