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(s), 130.3 (s), 132.9 (s), 133.6 (s), 151.7 (s), 154.3 (s), 165.8 (s). Anal. Calcd. for C23H18N2OS C=C (74.57%)
H (4.90%) N (7.56%) found C (74.85%) H (4.63%) N (7.73%).
5-Bromo-1-methyl-3-[2-(naphthalen-2-yl)-1,3-thiazol-4-yl]-1H-indole (4b)
Conditions: reflux for 1 h; cycloexane/ethyl acetate 7:3; light brown solid; yield 72%; mp:
124–125 ◦C; 1H NMR (200 MHz, DMSO-d6)
δ: 3.90 (s, 3H, CH3), 7.40 (dd, 1H, J = 1.8, 8.7 Hz, H-6”),
7.50 (d, 1H, J = 8.7, H-7”), 7.60 (m, 2H, ArH), 7.97–8.03 (m, 2H, H-4”, H-2”), 8.08–8.12 (m, 3H, ArH),
8.20 (dd, 1H, J = 1.8, 9.6 Hz, ArH), 8.40 (d, 1H, J = 1.8 Hz; ArH), 8.60 (s, 1H, H-5); 13C NMR (50 MHz,
DMSO-d6) δ: 32.9 (q), 109.6 (s), 111.0 (d), 112.4 (d), 112.9 (s), 112.5 (d), 116.4 (s), 123.5 (d), 124.2 (d),
125.4 (d), 126.5 (s), 127.0 (d), 127.2 (d), 127.8 (d), 128.5 (d), 128.9 (d), 130.6 (d), 132.9 (s), 133.6 (s), 135.7
(s), 150.8 (s), 166.2 (s). Anal. Calcd. for C22H15BrN2S C (63.01%) H (3.61%) N (6.68%) found C (62.89%)
H (3.85%) N (6.44%).
5-Fluoro-1-methyl-3-[2-(naphthalen-2-yl)-1,3-thiazol-4-yl]-1H-indole (4c)
◦
◦
Conditions: 60 C for 12 h; cycloexane/ethyl acetate 7:3; brown solid; yield 48%; mp: 151–152 C;
1H NMR (200 MHz, DMSO-d6)
: 3.90 (s, 3H, CH3), 7.15 (td, 1H, J = 2.4, 9.1 Hz, H-6”), 7.53–7.65
(m, 3H, ArH, H-7”, H-4”), 7.93 (s, 1H, H-2”), 7.98–8.04 (m, 2H, ArH), 8.07–8.15 (m, 3H, ArH), 8.22
(dd, 1H, J = 1.6, 8.6 Hz, ArH ), 8.61 (s, 1H, H-5); 13C NMR (50 MHz, DMSO-d6)
: 32.9 (q), 105.2 (d,
C-4”-F = 23.9 Hz), 109.6 (d), 110.1 (d), 110.4 (d), 111.4 (d), 111.6 (d), 123.6 (d), 125.0 (s), 125.1 (s), 125.3
δ
δ
J
(d), 127.0 (d), 127.5 (d JC-6”-F = 29.4 Hz), 128.7 (d, JC-7”-F = 16.3 Hz), 131.0 (d), 130.6 (s), 132.9 (s), 133.6
(s), 133.8 (s), 151.1 (s), 166.0 (s). Anal. Calcd. for C22H15FN2S C (73.72%) H (4.22%) N (7.82%) found C
(73.98%) H (4.56%) N (7.631%).
1-Methyl-3-[2-(naphthalen-2-yl)-1,3-thiazol-4-yl]-1H-indole (4d)
Conditions: reflux for 1 h; cycloexane/ethyl acetate 7:3; brown solid; yield 75%; mp: 174–175 ◦C;
1H NMR (200 MHz, DMSO-d6)
δ
: 3.90 (s, 3H, CH3), 7.19–7.32 (m, 2H, H-6”, H-7”), 7.52–7.65 (m, 2H,
H-4”, ArH), 7.88 (s, 1H, H-2”), 7.98–8.15 (m, 4H, ArH), 8.20–8.28 (m, 2H, ArH), 8.61 (s, 1H, H-5);
13C NMR (50 MHz, DMSO-d6)
: 109.9 (s), 110.2 (d), 110.3 (d), 120.0 (d), 120.3 (d), 121.7(d), 124.9 (s),
δ
125.3 (d), 126.7 (d), 127.0 (d), 127.1 (d), 127.8 (d), 128.6 (d), 128.9 (d), 129.2 (d), 130.7 (s), 132.9 (s), 133.6
(s), 137.0 (s), 151.6 (s), 165.9 (s). Anal. Calcd. for C22H16N2S C (77.62%) H (4.74%) N (8.23%) found C
(77.45%) H (4.79%) N (7.98%).
5-Methoxy-3-[2-(naphthalen-2-yl)-1,3-thiazol-4-yl]-1-(phenylsulfonyl)-1H-indole (4e)
Conditions: reflux for 1 h; cycloexane/ethyl acetate 9:1; white solid; yield 90%; mp: 168–169 ◦C;
IR: 1451, 1526 (SO2) cm−1; 1H NMR (200 MHz, DMSO-d6)
δ: 3.89 (s, 3H, CH3), 7.06 (dd, 1H, J = 2.5,
9.0 Hz, H-6”), 7.56–7.75 (m, 5H, H-7”, ArH), 7.82 (d; 1H, J = 2.5 Hz, H-4”), 7.92–8.14 (m, 6H, ArH), 8.23
(dd, 1H, J = 1.7, 8.6 Hz, ArH), 8.33 (s, 1H, H-2”), 8.44 (s, 1H, H-5), 8.64 (m, 1H, ArH); 13C NMR (50 MHz,
DMSO-d6) δ: 55.43 (q), 104.3 (d), 110.3 (s), 114.1 (d), 114.2 (d), 115.5 (d), 117.6 (s), 123.5 (d), 125.5 (d),
125.6 (d), 126.7 (d), 127.1 (dx2), 127.3 (d), 127.8 (d), 128.6 (d), 128.9 (d), 129.2 (s), 129.9 (dx2), 130.3 (s),
132.9 (s), 133.7 (s), 134.7 (d), 136.7 (s), 148.6 (s), 156.5 (s), 166.8 (s). Anal. Calcd. for C28H20N2O3S2 C
(67.72%) H (4.06%) N (5.64%) found C (67.55%) H (4.23%) N (5.77%).
5-Bromo-3-[2-(naphthalen-2-yl)-1,3-thiazol-4-yl]-1-(phenylsulfonyl)-1H-indole (4f)
Conditions: reflux for 6 h; cycloexane/ethyl acetate 8:2; white solid; yield 70%; mp: 216–217 ◦C;
IR: 1451, 1526 (SO2) cm−1; 1H NMR (200 MHz, DMSO-d6)
δ
: 7.57–7.78 (m, 6H, ArH), 7.96–8.04 (m, 2H,
ArH), 8.08–8.14 (m, 4H, ArH), 8.20 (dd, 1H, J = 1.8, 8.1 Hz, ArH), 8.38 (s, 1H, H-2”), 8.52 (d, 1H, J = 1.8,
ArH), 8.56 (s, 1H, H-5), 8.62 (s, 1H, ArH); 13C NMR (50 MHz, DMSO-d6)
: 115.3 (d),116.1 (d), 116.8 (s),
δ
117.0 (s), 123.5 (d), 124.2 (d), 125.7 (d), 126.1 (d), 126.8 (d), 127.1 (dx2), 127.4 (d), 127.8 (d), 128.0 (d),
128.6 (d), 129.0 (d), 129.6 (s), 130.0 (dx2), 130.2 (s), 132.9 (s), 133.5 (s), 133.7 (s), 135.0 (d), 136.5 (s), 147.9