G. Wang et al. / Bioorg. Med. Chem. 22 (2014) 2060–2079
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5.1.4.5. (E)-1-(5-Methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(1-
(methoxymethyl)-1H-indol-3-yl)prop-2-en-1-one (7). The
J = 6.8 Hz), 5.63 (d, 1H, J = 10.0 Hz), 6.52 (d, 1H, J = 8.0 Hz), 6.71
(d, 1H, J = 10.0 Hz), 7.22 (d, 1H, J = 8.0 Hz), 7.29 (t, 1H, J = 8.0 Hz),
7.36 (d, 1H, J = 8.0 Hz), 7.46 (s, 1H), 7.75–7.78 (m, 2H), 7.99 (d,
1H, J = 15.6 Hz), 8.06 (d, 1H, J = 8.0 Hz); 13C NMR (CDCl3,
100 MHz) d: 18.1, 25.7, 27.9, 27.9, 44.4, 55.8, 76.9, 103.3, 110.3,
110.5, 113.4, 116.9, 118.7, 121.1, 122.3, 122.8, 126.5, 128.8,
131.8, 133.0, 136.4, 137.6, 138.0, 153.4, 158.0, 190.1; HRMS (ESI)
calcd for [M+H]+ C28H30NO3: 428.2226, found: 428.2221.
reaction was carried out following the general procedure B with
7a (189 mg, 1 mmol) to give 7 as a yellow solid (149 mg, 37%).
1H NMR (CDCl3, 400 MHz) d: 1.53 (s, 6H), 3.28 (s, 3H), 3.89 (s,
3H), 5.47 (s, 2H), 5.64 (d, 1H, J = 10.0 Hz), 6.52 (d, 1H, J = 8.8 Hz),
6.71 (d, 1H, J = 10.0 Hz), 7.28 (d, 1H, J = 8.0 Hz), 7.34 (t, 1H,
J = 8.0 Hz), 7.51 (s, 1H), 7.52 (d, 1H, J = 8.0 Hz), 7.60 (d, 1H,
J = 8.0 Hz), 7.81 (d, 1H, J = 16.0 Hz), 7.97 (d, 1H, J = 16.0 Hz), 8.08
(d, 1H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz) d: 28.0, 28.0, 55.8,
56.2, 77.0, 77.8, 103.4, 110.5, 110.8, 114.6, 116.9, 121.2, 121.7,
122.2, 123.5, 123.8, 126.7, 128.8, 131.8, 133.2, 135.4, 137.6,
153.5, 158.1, 190.1; HRMS (ESI) calcd for [M+H]+ C25H26NO4:
404.1862, found: 404.1858.
5.1.4.10. (E)-1-(5-Methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(1-
(2-morpholinoethyl)-1H-indol-3-yl)prop-2-en-1-one (12). The
reaction was carried out following the general procedure B with
12a (189 mg, 1 mmol) to give 12 as a yellow solid (111 mg, 26%).
1H NMR (400 MHz, CDCl3) d: 1.53 (s, 6H), 2.49 (t, 4H, J = 4.4 Hz),
2.77 (t, 2H, J = 6.4 Hz), 3.70 (t, 4H, J = 4.4 Hz), 3.89 (s, 3H), 4.25 (t,
2H, J = 6.4 Hz), 5.64 (d, 1H, J = 10.0 Hz), 6.52 (d, 1H, J = 8.8 Hz),
6.71 (d, 1H, J = 10.0 Hz), 7.22 (d, 1H, J = 8.0 Hz), 7.30 (t, 1H,
J = 8.0 Hz), 7.38 (d, 1H, J = 8.0 Hz), 7.52 (s, 1H), 7.75 (d, 1H,
J = 8.8 Hz), 7.76 (d, 1H, J = 15.6 Hz), 7.98 (d, 1H, J = 15.6 Hz), 8.07
(d, 1H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz) d: 28.0, 28.0, 44.1,
53.8, 53.8, 55.8, 55.8, 57.8, 66.9, 76.9, 103.4, 110.0, 110.5, 113.6,
116.9, 121.1, 121.3, 122.4, 122.7, 122.9, 126.2, 128.8, 131.8, 133.9,
136.0, 137.5, 153.4, 158.0, 190.1; HRMS (ESI) calcd for [M+H]+
C29H33N2O4: 473.2440, found: 473.2445.
5.1.4.6. (E)-1-(5-Methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(1-
methyl-1H-indol-3-yl)prop-2-en-1-one (8). The reaction was
carried out following the general procedure B with 8a (189 mg,
1 mmol) to give 8 as a yellow solid (153 mg, 41%). 1H NMR
(400 MHz, CDCl3) d: 1.52 (s, 6H), 3.83 (s, 3H), 3.89 (s, 3H), 5.63
(d, 1H, J = 10.0 Hz), 6.51 (d, 1H, J = 8.8 Hz), 6.71 (d, 1H,
J = 10.0 Hz), 7.23 (d, 1H, J = 7.2 Hz), 7.30–7.37 (m, 2H), 7.39 (s,
1H), 7.74 (d, 1H, J = 8.8 Hz), 7.75 (d, 1H, J = 16.0 Hz), 7.97 (d, 1H,
J = 16.0 Hz), 8.07 (d, 1H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz) d:
28.0, 28.0, 33.2, 55.8, 76.9, 103.3, 110.0, 110.5, 113.5, 116.9,
121.1, 121.1, 122.4, 122.7, 122.9, 126.2, 128.8, 131.7, 134.2,
135.9, 138.2, 153.4, 158.0, 190.2; HRMS (ESI) calcd for [M+H]+
C24H24NO3: 374.1756, found: 374.1752.
5.1.4.11.
(E)-3-(1-Benzyl-1H-indol-3-yl)-1-(5-methoxy-2,2-
dimethyl-2H-chromen-8-yl)prop-2-en-1-one (13). The reac-
tion was carried out following the general procedure B with 13a
(189 mg, 1 mmol) to give 13 as a yellow solid (189 mg, 42%). 1H
NMR (400 MHz, CDCl3) d: 1.51 (s, 6H), 3.88 (s, 3H), 5.32 (s, 2H),
5.63 (d, 1H, J = 10.0 Hz), 6.51 (d, 1H, J = 8.8 Hz), 6.70 (d, 1H,
J = 10.0 Hz), 7.15–7.16 (m, 2H), 7.22–7.25 (m, 2H), 7.27–7.32 (m,
4H), 7.44 (s, 1H), 7.74 (d, 1H, J = 8.8 Hz), 7.97 (d, 1H, J = 16.0 Hz),
8.08 (d, 1H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz) d: 28.0, 28.0,
50.5, 55.8, 76.9, 103.4, 110.5, 110.5, 114.0, 116.9, 121.2, 121.3,
122.3, 123.0, 123.1, 126.4, 127.0, 127.0, 128.1, 128.8, 129.0,
129.0, 131.8, 133.5, 135.9, 136.2, 137.8, 153.4, 158.0, 190.1; HRMS
(ESI) calcd for [M+H]+ C30H28NO3: 450.2069, found: 450.2061.
5.1.4.7.
(E)-3-(1-Ethyl-1H-indol-3-yl)-1-(5-methoxy-2,2-
dimethyl-2H-chromen-8-yl)prop-2-en-1-one (9). The reaction
was carried out following the general procedure B with 9a
(189 mg, 1 mmol) to give 9 as a yellow solid (154 mg, 40%). 1H
NMR (400 MHz, CDCl3) d: 1.21 (t, 3H, J = 7.2 Hz), 1.52 (s, 6H),
3.45 (q, 2H, J = 7.2 Hz), 3.88 (s, 3H), 3.63 (d, 1H, J = 10.0 Hz), 6.51
(d, 1H, J = 8.8 Hz), 6.71 (d, 1H, J = 10.0 Hz), 7.22 (d, 1H, J = 8.0 Hz),
7.30 (t, 1H, J = 8.0 Hz), 7.37 (d, 1H, J = 8.0 Hz), 7.45 (s, 1H), 7.75
(d, 1H, J = 8.8 Hz), 7.76 (d, 1H, J = 15.6 Hz), 7.98 (d, 1H,
J = 15.6 Hz), 8.07 (d, 1H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz) d:
15.2, 28.0, 28.0, 41.4, 55.8, 76.9, 103.3, 110.1, 110.5, 113.5, 116.9,
121.0, 121.2, 122.4, 122.6, 122.8, 126.3, 128.8, 131.7, 132.6,
136.1, 137.3, 153.4, 158.0, 190.2; HRMS (ESI) calcd for [M+H]+
C25H26NO3: 388.1913, found: 388.1907.
5.1.4.12. (E)-3-(1-(2-Fluorobenzyl)-1H-indol-3-yl)-1-(5-methoxy-
2,2-dimethyl-2H-chromen-8-yl)prop-2-en-1-one
(14). The
reaction was carried out following the general procedure B with
14a (189 mg, 1 mmol) to give 14 as a yellow solid (215 mg, 46%).
1H NMR (400 MHz, CDCl3) d: 1.52 (s, 6H), 3.88 (s, 3H), 5.37 (s, 2H),
5.63 (d, 1H, J = 10.0 Hz), 6.51 (d, 1H, J = 8.8 Hz), 6.70 (d, 1H,
J = 10.0 Hz), 6.98 (t, 1H, J = 7.2 Hz), 7.05 (t, 1H, J = 7.2 Hz), 7.10 (t,
1H, J = 8.8 Hz), 7.23–7.30 (m, 3H), 7.37 (d, 1H, J = 7.2 Hz), 7.50 (s,
1H), 7.75 (d, 1H, J = 8.8 Hz), 7.77 (d, 1H, J = 16.0 Hz), 7.98 (d, 1H,
J = 16.0 Hz), 8.07 (d, 1H, J = 7.2 Hz); 13C NMR (CDCl3, 100 MHz) d:
28.0, 28.0, 44.2, 55.8, 76.9, 103.4, 110.3, 110.5, 114.2, 115.6, 115.8,
116.9, 121.2, 121.3, 122.2, 123.1, 123.2, 124.7, 126.4, 128.8, 129.2,
130.0, 130.1, 131.8, 133.4, 135.8, 137.6, 153.5, 158.1, 190.0; HRMS
(ESI) calcd for [M+H]+ C30H27FNO3: 468.1975, found: 468.1976.
5.1.4.8.
(E)-3-(1-Isopropyl-1H-indol-3-yl)-1-(5-methoxy-2,2-
dimethyl-2H-chromen-8-yl)prop-2-en-1-one (10). The reac-
tion was carried out following the general procedure B with 10a
(189 mg, 1 mmol) to give 10 as a yellow solid (132 mg, 33%). 1H
NMR (400 MHz, CDCl3) d: 1.63 (s, 6H), 1.55 (d, 6H, J = 6.8 Hz),
3.88 (s, 3H), 4.67 (heptet, 1H, J = 6.8 Hz), 5.63 (d, 1H, J = 10.0 Hz),
6.51 (d, 1H, J = 8.8 Hz), 6.71 (d, 1H, J = 10.0 Hz), 7.22 (d, 1H,
J = 8.0 Hz), 7.29 (t, 1H, J = 8.0 Hz), 7.55 (s, 1H), 7.75 (d, 1H,
J = 8.8 Hz), 7.76 (d, 1H, J = 15.6 Hz), 7.99 (d, 1H, J = 15.6 Hz), 8.07
(d, 1H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz) d: 22.7, 22.7, 27.9,
27.9, 47.5, 55.8, 76.9, 103.3, 110.2, 110.5, 113.7, 116.9, 121.1,
121.2, 122.5, 122.5, 122.7, 126.3, 128.8, 129.5, 131.7, 136.2,
137.2, 153.4, 157.9, 190.1; HRMS (ESI) calcd for [M+H]+
C26H28NO3: 402.2069, found: 402.2066.
5.1.4.13. (E)-3-(1-(3-Fluorobenzyl)-1H-indol-3-yl)-1-(5-methoxy-
2,2-dimethyl-2H-chromen-8-yl)prop-2-en-1-one (15). The reac-
tion was carried out following the general procedure B with 15a
(189 mg, 1 mmol) to give 15 as a yellow solid (187 mg, 40%). 1H
NMR (400 MHz, CDCl3) d: 1.52 (s, 6H), 3.88 (s, 3H), 5.32 (s, 2H),
5.63 (d, 1H, J = 10.0 Hz), 6.51 (d, 1H, J = 8.8 Hz), 6.71 (d, 1H,
J = 10.0 Hz), 6.82 (d, 1H, J = 8.0 Hz), 6.91 (d, 1H, J = 8.0 Hz), 6.96 (t,
1H, J = 8.0 Hz), 7.27–7.31 (m, 4H), 7.45 (s, 1H), 7.75 (d, 1H,
J = 8.8 Hz), 7.79 (d, 1H, J = 15.6 Hz), 7.98 (d, 1H, J = 15.6 Hz), 8.09 (d,
1H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz) d: 28.0, 28.0, 49.9, 55.8,
76.9, 103.4, 110.4, 110.5, 113.8, 114.0, 114.2, 114.9, 115.1, 116.9,
5.1.4.9. (E)-1-(5-Methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(1-
(3-methylbut-2-en-1-yl)-1H-indol-3-yl)prop-2-en-1-one
(11). The reaction was carried out following the general proce-
dure B with 11a (189 mg, 1 mmol) to give 11 as a yellow solid
(167 mg, 39%). 1H NMR (400 MHz, CDCl3) d: 1.52 (s, 6H), 1.80 (s,
3H), 1.83 (s, 3H), 3.89 (s, 3H), 4.69 (d, 2H, J = 6.8 Hz), 5.40 (t, 1H,