94 R. V. S. Nirogi et al.
J Enzyme Inhib Med Chem, 2015; 30(1): 85–97
N0-[5-(5-bromo indole-1-sulfonyl)-2-ethyl phenyl]-N,
N-dimethyl ethane-1,2-diamine (9m)
CDCl3): ꢁ 1.16–1.20 (3H, t, J ¼ 7.45 Hz), 2.22 (6H, s), 2.39–
2.45 (2H, q, J ¼ 7.49 Hz), 2.55–2.57 (2H, t, J ¼ 5.67 Hz), 3.06–
3.10 (2H, q, J ¼ 5.08 Hz), 4.67 (1H, bs), 6.56–6.57 (1H, d,
J ¼ 3.69 Hz), 6.91 (1H, d, J ¼ 1.89 Hz), 7.05–7.07 (1H, d,
J ¼ 7.90 Hz), 7.12–7.15 (1H, dd, J ¼ 7.9, 1.96 Hz), 7.23–7.24
(1H, d, J ¼ 2.04 Hz), 7.49–7.52 (1H, dd, J ¼ 9.89, 1.99 Hz), 7.58–
7.59 (1H, d, J ¼ 3.66 Hz), 7.92–7.94 (1H, d, J ¼ 8.8 Hz); HRMS:
[M + H]+ C20H25ClN3O2S calc. 406.1356, found. 406.1354.
HPLC (%): 98.66; IR (cmꢂ1): 3388, 1571, 1369, 1170; ESI-MS
(m/z): 450.6, 452.6 (M + H)+; 1H-NMR (400 MHz, CDCl3): ꢁ
1.15–1.18 (3H, t, J ¼ 7.48 Hz), 2.23 (6H, s), 2.39–2.45 (2H, q,
J ¼ 7.48 Hz), 2.55–2.58 (2H, t, J ¼ 5.64 Hz), 3.07–3.11 (2H, q,
t ¼ 5.16 Hz), 4.69 (1H, bs), 6.56–6.57 (1H, d, J ¼ 3.69 Hz), 6.90–
6.91 (1H, d, J ¼ 1.9 Hz), 7.05–7.07 (1H, d, J ¼ 7.91 Hz), 7.12–
7.15 (1H, dd, J ¼ 7.88, 1.92 Hz), 7.37–7.39 (1H, dd, J ¼ 8.80,
1.92 Hz), 7.56–7.57 (1H, d, J ¼ 3.36 Hz), 7.65 (1H, d,
J ¼ 1.83 Hz), 7.87–7.89 (1H, d, J ¼ 8.82 Hz); HRMS: [M + H]+
C20H25BrN3O2S calc. 450.0851, found. 450.0849.
N0-[3-(5-bromo indole-1-sulfonyl) phenyl]-N, N-dimethyl
ethane-1,2-diamine (9s)
HPLC (%): 97.54; IR (cmꢂ1): 3311, 1600, 1369, 1172; ESI-MS
(m/z): 422.5, 424.5 (M + H)+; 1H-NMR (400 MHz, CDCl3):
ꢁ 2.28 (6H, s), 2.58–2.61 (2H, t, J ¼ 5.87 Hz), 3.10–3.13 (2H,
t, J ¼ 5.57 Hz), 4.96 (1H, bs), 6.58–6.59 (1H, d, J ¼ 3.60 Hz),
6.70–6.73 (1H, m), 6.96–6.97 (1H, t, J ¼ 2.08 Hz), 7.08–7.11 (1H,
m), 7.15–7.19 (1H, dt, J ¼ 7.88 Hz), 7.38–7.40 (1H, dd, J ¼ 8.81,
1.9 Hz), 7.55 (1H, d, J ¼ 3.64 Hz), 7.66 (1H, d, J ¼ 1.8 Hz), 7.85–
7.87 (1H, d, J ¼ 8.81 Hz); HRMS: [M + H]+ C18H21BrN3O2S
calc. 422.0538, found. 422.0536.
N0-[3-(4-chloro-3-methyl indole-1-sulfonyl) phenyl]-N,
N-dimethyl ethane-1,2-diamine (9n)
HPLC (%): 95.06; IR (cmꢂ1): 3390, 1600, 1367, 1174; ESI-MS
(m/z): 392.3, 394.3 (M + H)+; 1H-NMR (400 MHz, CDCl3): ꢁ
2.24 (6H, s), 2.46 (3H, s), 2.53–2.55 (2H, t, J ¼ 5.64 Hz), 3.06–
3.10 (2H, t, J ¼ 5.63 Hz), 4.71 (1H, bs), 6.72 (1H, m), 6.97–6.98
(1H, dt, J ¼ 2.1 Hz), 7.08–7.11 (1H, m), 7.13–7.19 (3H, m), 7.30
(1H, d, J ¼ 1.22 Hz), 7.86–7.89 (1H, dd, J ¼ 9.17, 2.53 Hz);
HRMS: [M + H]+ C19H23ClN3O2S calc. 392.1199, found.
392.1202.
N0-[3-(4-chloro indole-1-sulfonyl) phenyl]-N, N-dimethyl
ethane-1,2-diamine (9t)
HPLC (%): 96.30; IR (cmꢂ1): 3371, 1600, 1371, 1166; ESI-MS
(m/z): 378.5, 380.5 (M + H)+; 1H-NMR (400 MHz, CDCl3): ꢁ
2.29 (6H, s), 2.60–2.63 (2H, t, J ¼ 5.64 Hz), 3.11–3.14 (2H,
t, J ¼ 5.56 Hz), 5.29 (1H, bs), 6.69–6.72 (1H, m), 6.75–6.76
(1H, d, J ¼ 3.72 Hz), 6.95–6.96 (1H, t, J ¼ 2.09 Hz), 7.10–7.12
(1H, m), 7.15–7.19 (1H, t, J ¼ 7.84 Hz), 7.20–7.22 (2H, m), 7.58–
7.59 (1H, d, J ¼ 3.7 Hz), 7.86–7.90 (1H, m); HRMS: [M + H]+
C18H21ClN3O2S calc. 378.1043, found. 378.1045.
N0-[2-ethyl-5-(5-fluoro-3-methyl indole-1-sulfonyl)
phenyl]-N, N-dimethyl ethane-1,2-diamine (9o)
HPLC (%): 98.52; MR (ꢁC): 105.4–108.2; IR (cmꢂ1): 3404, 1595,
1359, 1178; ESI-MS (m/z): 404.4 (M + H)+; 1H-NMR (400 MHz,
CDCl3): ꢁ 1.16–1.19 (3H, t, J ¼ 7.45 Hz), 2.19–2.20 (3H, s), 2.22
(6H, s), 2.39–2.44 (2H, q, J ¼ 7.49 Hz), 2.54–2.57 (2H, t,
J ¼ 5.67 Hz), 3.06–3.10 (2H, q, J ¼ 4.89 Hz), 4.64 (1H, bs), 6.92
(1H, d, J ¼ 1.85 Hz), 7.01–7.12 (4H, m), 7.33 (1H, d,
J ¼ 0.92 Hz), 7.92–7.95 (1H, dd, J ¼ 4.38 Hz); HRMS: [M + H]+
C21H27FN3O2S calc. 404.1808, found. 404.1806.
N0-[5-(5-bromo-3-methyl indole-1-sulfonyl)-2-ethyl
phenyl]-N, N-dimethyl ethane-1,2-diamine (9u)
N0-[3-(5-isopropoxy-3-methyl indole-1-sulfonyl) phenyl]-
N, N-dimethyl ethane-1,2-diamine (9p)
HPLC (%): 99.25; MR (ꢁC): 105.4–108.2; IR (cmꢂ1): 3373, 1597,
1367, 1166; ESI-MS (m/z): 464.7, 466.7 (M + H)+; 1H-NMR
(400 MHz, CDCl3): ꢁ 1.15–1.19 (3H, t, J ¼ 7.44 Hz), 2.20 (3H, s),
2.28 (6H, s), 2.61–2.64 (2H, t, J ¼ 5.97 Hz), 2.96–3.02 (2H, q,
J ¼ 7.3 Hz), 3.13–3.16 (2H, t, J ¼ 5.65 Hz), 4.75 (1H, bs), 6.89–
6.90 (1H, d, J ¼ 1.85 Hz), 7.04–7.06 (1H, d, J ¼ 7.93 Hz), 7.10–
7.12 (1H, dd, J ¼ 7.88, 1.89 Hz), 7.37–7.39 (1H, dd, J ¼ 8.78,
1.91 Hz), 7.57 (1H, s), 7.76–7.78 (1H, d, J ¼ 8.3 Hz), 7.87–7.89
(1H, d, J ¼ 8.82 Hz); HRMS: [M + H]+ C21H27BrN3O2S calc.
464.1007, found. 464.1009.
HPLC (%): 96.13; MR (ꢁC): 86.24; IR (cmꢂ1): 3387, 2978, 1602,
1359, 1176; ESI-MS (m/z): 416.3 (M + H)+; 1H-NMR (400 MHz,
CDCl3): ꢁ 1.32–1.33 (6H, d, J ¼ 6.0 Hz), 2.18 (3H, s), 2.23 (6H,
s), 2.51–2.54 (2H, t, J ¼ 5.65 Hz), 3.05–3.07 (2H, q, J ¼ 4.98 Hz),
4.50–4.56 (1H, sept, J ¼ 6.0Hz), 4.64 (1H, bs), 6.66–6.69 (1H, m),
6.88–6.90 (2H, m), 6.98–6.99 (1H, t, J ¼ 3.04 Hz), 7.07–7.09 (1H,
m), 7.12–7.16 (1H, t, J ¼ 7.84 Hz), 7.23 (1H, s), 7.84–7.86 (1H,
dd, J ¼ 7.8, 1.8 Hz); HRMS: [M + H]+ C22H30N3O3S calc.
416.2008, found. 416.2010.
N0-[3-(5-ethoxy-3-methyl indole-1-sulfonyl) phenyl]-
N,N-dimethyl ethane-1,2-diamine (9v)
N0-[3-(5-isopropoxy indole-1-sulfonyl) phenyl]-N,
N-dimethyl ethane-1,2-diamine (9q)
HPLC (%): 97.12; IR (cmꢂ1): 3390, 1602, 1363, 1172; ESI-MS
1
(m/z): 402.5 (M + H)+; H-NMR (400 MHz, CDCl3): ꢁ 1.40–1.43
HPLC (%): 97.46; IR (cmꢂ1): 3387, 2974, 1600, 1367, 1174; ESI-
MS (m/z): 402.3 (M + H)+; 1H-NMR (400 MHz, CDCl3): ꢁ 1.31–
1.33 (6H, d, J ¼ 6.0 Hz), 2.22 (6H, s), 2.50–2.53 (2H, t,
J ¼ 5.64 Hz), 3.03–3.07 (2H, t, J ¼ 5.04 Hz), 4.47–4.53 (1H, m),
4.61(1H, bs), 6.54–6.55 (1H, d, J ¼ 3.6 Hz), 6.70 (1H, m), 6.88–
6.91 (1H, dd, J ¼ 8.96, 2.44 Hz), 6.97 (1H, d, J ¼ 2.36 Hz), 6.98–
6.99 (1H, t, J ¼ 1.96 Hz), 7.11 (1H, m), 7.14–7.16 (1H, dt,
J ¼ 7.92 Hz), 7.48–7.49 (1H, d, J ¼ 3.64 Hz), 7.85–7.87 (1H, d,
J ¼ 9.0 Hz); HRMS: [M + H]+ C21H28N3O3S calc. 402.1851,
found. 402.1849.
(3H, t, J ¼ 6.99 Hz), 2.19 (3H, s), 2.22 (6H, s), 2.49–2.52 (2H, t,
J ¼ 5.98 Hz), 3.03–3.07 (2H, q, J ¼ 5.01 Hz), 4.02–4.07 (2H, q,
J ¼ 6.98 Hz), 4.56–4.58 (1H, bs), 6.66–6.68 (1H, m), 6.86 (1H, d,
J ¼ 2.38 Hz), 6.89–6.92 (1H, dd, J ¼ 8.92, 2.46 Hz), 6.98–6.99
(1H, t, J ¼ 2.07 Hz), 7.06–7.09 (1H, m), 7.12–7.16 (1H, dt,
J ¼ 7.84 Hz), 7.24 (1H, s), 7.85–7.87 (1H, d, J ¼ 8.95 Hz); HRMS:
[M + H]+ C21H28N3O3S calc. 402.1851, found. 402.1848.
N0-[3-(5-chloro-3-methyl indole-1-sulfonyl)-2-ethyl
phenyl]-N, N-dimethyl ethane-1,2-diamine (9w)
N0-[2-ethyl-5-(5-chloro indole-1-sulfonyl) phenyl]-
N,N-dimethyl ethane-1,2-diamine (9r)
HPLC (%): 98.28; IR (cmꢂ1): 3390, 1597, 1367, 1168; ESI-MS
(m/z): 420.2, 422.2 (M + H)+; 1H-NMR (400 MHz, CDCl3):
ꢁ 1.16–1.19 (3H, t, J ¼ 7.48 Hz), 2.20 (3H, s), 2.23 (6H, s),
2.39–2.44 (2H, q, J ¼ 7.48 Hz), 2.55–2.57 (2H, t, J ¼ 5.66 Hz),
HPLC (%): 99.34; IR (cmꢂ1): 3390, 1597, 1369, 1168;
ESI-MS (m/z): 406.3, 408.3 (M + H)+; 1H-NMR (400 MHz,