6278 Journal of Medicinal Chemistry, 2004, Vol. 47, No. 25
Coowar et al.
NMR (200 MHz): δ 1.31 (s br, 8H, H-12 to 15), 1.48 (m, 2H,
H-16), 1.61 (m, 2H, H-11), 2.30 (q, J ) 6.9 Hz, 2H, H-10), 3.46
(t, J ) 6.4 Hz, 2H, H-17), 3.77 (s, 3H, -OCH3), 3.82 (s, 3H,
-OCH3), 4.50 (s, 2H, H-18), 5.80 (dt, J ) 11.3 Hz, J ) 6.9 Hz,
1H, H-9), 6.34 (d, J ) 11.3 Hz, 1H, H-8), 6.85 (d, J ) 8.9 Hz,
2H, H-3′′,5′′), 6.89-6.94 (m, 2H, H-4,6), 7.33 (m, 5H, H-2′′′ to
6′′′), 7.45 (s, 1H, H-2), 7.78 (d, J ) 8.9 Hz, 2H, H-2′′,6′′), 7.87
(d, J ) 9.6 Hz, 1H, H-7). 13C NMR (50 MHz): δ 26.2 (C-10),
29.5-29.8 (C-11 to 16), 55.7 (-OCH3), 70.6 (C-17), 72.9 (C-
18), 102.0 (C-4), 113.9 (C-6), 114.4 (C-3′′,5′′), 114.6 (C-3), 117.6
(C-7), 119.4 (C-3′), 124.3 (C-2), 127.5 (C-8), 127.7 (C-2′′′,6′′′),
128.4 (C-3′′′,5′′′), 129.0 (C-2′′,6′′), 129.2 (C-4′′′), 129.6 (C-7′),
131.9 (C-1′′), 134.9 (C-9), 138.5 (C-1′′′), 156.4 (C-5), 163.7 (C-
4′′).
3-(10-Benzyloxy-dec-1-enyl)-6-methoxy-1-(4-methoxy-
benzenesulfonyl)-1H-indole (11d, n ) 10). Yield: 91%. 1H
NMR (300 MHz): δ 1.31 (s br, 8H, H-12 to 15), 1.48 (m, 2H,
H-16), 1.61 (m, 2H, H-11), 2.30 (q, J ) 6.7 Hz, 2H, H-10), 3.46
(t, J ) 6.6 Hz, 2H, H-17), 3.78 (s, 3H, -OCH3), 3.88 (s, 3H,
-OCH3), 4.50 (s, 2H, H-18), 5.79 (dt, J ) 11.5 Hz, J ) 6.7 Hz,
1H, H-9), 6.35 (d, J ) 11.5 Hz, 1H, H-8), 6.87 (d, J ) 8.9 Hz,
2H, H-3′′,5′′), 6.88 (m, 1H, H-5), 7.33 (m, 6H, H-4, H-2′′′ to
6′′′), 7.39 (s, 1H, H-2), 7.52 (d, J ) 2.0 Hz, 1H, H-7), 7.80 (d, J
) 8.9 Hz, 2H, H-2′′,6′′). 13C NMR (75 MHz): δ 26.2 (C-10),
29.3-29.8 (C-11 to 16), 55.6, 55.8 (-OCH3), 70.5 (C-17), 72.8
(C-18), 97.9 (C-7), 112.3 (C-5), 114.4 (C-3′′,5′′), 117.5 (C-4),
119.2 (C-3), 120.0 (C-2), 122.2 (C-8), 124.7 (C-3′), 127.4-128.9
(C-2′′,6′′, C-2′′′ to 6′′′), 129.6 (C-1′′), 134.7 (C-9), 135.6 (C-7′),
138.7 (C-1′′′), 158.1 (C-6), 163.7 (C-4′′). IR (CsI): 2925, 2853
(s, C-H), 1642, 1595 (m, CdC), 1497 (m, C-H), 1264 (m,
C-O), 1095 (m, C-O), 676 (m, C-H).
(-OCH3), 70.5 (C-23), 72.8 (C-24), 97.4 (C-7), 100.9 (C-4), 114.3
(C-3′′,5′′), 117.6 (C-2), 119.6 (C-3), 122.2 (C-8), 123.8 (C-3′),
127.6-128.8 (C-2′′,6′′,2′′′ to 6′′′), 29.0 (C-7′), 129.6 (C-1′′), 134.8
(C-9), 138.7 (C-1′′′), 147.1 (C-6); 148.2 (C-5), 163.7 (C-4′′). Anal.
Calcd C: 71.08 H: 7.90 N: 2.07. Found C: 71.20 H: 8.07 N: 2.16.
IR (CsI): 2925, 2853 (s, C-H), 1648, 1596 (m, CdC), 1486 (m,
C-H), 1263 (m, C-O), 1094 (m, C-O), 675 (m, C-H).
5-Methoxy-1-(4-methoxy-benzenesulfonyl)-3-pentadec-
1-enyl-1H-indole (11h). Yield: 76%. 1H NMR (300 MHz): δ
0.87 (t, J ) 6.7 Hz, 3H, H-22), 1.25 (s br, 20H, H-12 to 21),
1.47 (m, 2H, H-11), 2.30 (q, J ) 4.4 Hz, 2H, H-10), 3.77 (s, 3H,
-OCH3), 3.82 (s, 3H, -OCH3), 5.80 (dt, J ) 11.4 Hz, J ) 6.9
Hz, 1H, H-9), 6.35 (d, J ) 11.4 Hz, 1H, H-8), 6.86 (d, J ) 9.0
Hz, 2H, H-3′′,5′′), 6.89-6.94 (m, 2H, H-4,6), 7.45 (s, 1H, H-2),
7.77 (d, J ) 9.0 Hz, 2H, H-2′′,6′′), 7.87 (d, J ) 9.6 Hz, 1H,
H-7). 13C NMR (50 MHz): δ 14.6 (C-22), 26.2 (C-10), 29.3-
29.8 (C-11 to 21), 55.6 (-OCH3), 56.2 (-OCH3), 102.1 (C-4),
113.9 (C-6), 114.4 (C-3′′,5′′), 114.6 (C-3), 117.5 (C-7), 119.4 (C-
3′), 124.2 (C-2), 127.5 (C-8), 128.9 (C-2′′,6′′), 129.8 (C-7′), 131.9
(C-1′′), 134.7 (C-9), 156.4 (C-5), 163.6 (C-4′′). Anal. Calcd C:
70.82 H: 8.24 N: 2.66. Found C: 70.93 H: 8.31 N: 2.70.
10-[4-Methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-
3-yl]decan-1-ol (12b, n ) 10). To a solution of alkene 11b
(n ) 10) (350 mg, 0.62 mmol, 1 equiv) in ethanol (6 mL) was
added palladium on charcoal (5%, 35 mg, 10% w/w). The
mixture was stirred under 1 atm of hydrogen for 4 h at room
temperature. The mixture was then filtered on Celite and then
concentrated. The residue was purified by flash chromatog-
raphy using hexane-AcOEt (70-30) to give a white solid (277
mg, 93%). 1H NMR (300 MHz): δ 1.27 (s br, 12H, H-10 to 15),
1.59 (m, 4H, H-9,16), 2.76 (t, J ) 7.3 Hz, 2H, H-8), 3.64 (t, J
) 6.2 Hz, 2H, H-17), 3.78 (s, 3H, -OCH3), 3.85 (s, 3H, -OCH3),
6.61 (d, J ) 8.2 Hz, 1H, H-5), 6.85 (d, J ) 8.9 Hz, 2H, H-3′′,5′′),
7.15 (s, 1H, H-2), 7.18 (t, J ) 8.2 Hz, 1H, H-6), 7.56 (d, J )
8.2 Hz, 1H, H-7), 7.77 (d, J ) 8.9 Hz, 2H, H-2′′,6′′). 13C NMR
(75 MHz): δ 25.7 (C-15), 26.9 (C-9), 29.3-29.8 (C-8,10 to 14),
32.8 (C-16), 55.2, 55.6 (-OCH3), 63.1 (C-17), 103.6 (C-5), 106.6
(C-7), 114.3 (C-3′′,5′′), 120.6 (C-3), 121.2 (C-6), 124.1 (C-3′),
125.3 (C-2), 128.9 (C-2′′,6′′), 129.8 (C-1′′), 137.0 (C-7′), 154.6
(C-4), 163.5 (C-4′′).
3-(16-Benzyloxy-hexadec-1-enyl)-7-methoxy-1-(4-meth-
oxy-benzenesulfonyl)-1H-indole (11e, n ) 16). Yield: 77%.
1H NMR (300 MHz): δ 1.25 (s br, 20H, H-12 to 21), 1.51 (m,
2H, H-22), 1.60 (m, 2H, H-11), 2.37 (q, J ) 6.9 Hz, 2H, H-10),
3.46 (t, J ) 6.6 Hz, 2H, H-23), 3.73 (s, 3H, -OCH3), 3.83 (s,
3H, -OCH3), 4.50 (s, 2H, H-24), 5.82 (dt, J ) 11.3 Hz, J ) 6.9
Hz, 1H, H-9), 6.41 (d, J ) 11.3 Hz, 1H, H-8), 6.70 (d, J ) 6.7
Hz, 1H, H-6), 6.92 (d, J ) 8.9 Hz, 2H, H-3′′,5′′), 7.15 (d, J )
6.7 Hz, 1H, H-4), 7.28-7.33 (m, 5H, H-2′′′ to 6′′′), 7.35 (s, 1H,
H-2), 7.79 (m, 1H, H-5), 7.80 (d, J ) 8.9 Hz, 2H, H-2′′,6′′). 13
C
yield, %
NMR (75 MHz): δ 26.2 (C-10), 29.4-29.8 (C-11 to 22), 55.6
(-OCH3), 70.5 (C-23), 72.8 (C-24), 107.1 (C-6), 112.1 (C-4),
113.9 (C-3′′,5′′), 117.5 (C-5), 123.8 (C-8), 126.0 (C-3), 127.4 (C-
4′′′), 127.6 (C-2′′′,6′′′), 128.3 (C-2′′,6′′), 129.6 (C-3′′′,5′′′), 131.7
(C-1′′), 132.6 (C-7′), 133.7 (C-3′), 134.4 (C-9), 138.7 (C-1′′′),
147.4 (C-7), 163.2 (C-4′′). Anal. Calcd C: 72.52 H: 7.96 N: 2.17.
Found C: 72.13 H: 7.81 N: 2.06.
n
12a
12b
12c
12d
12f
12g
10
12
14
16
18
92
92
93
92
46
93
94
57
47
50
91
83
91
91
94
80
85
92
47
85
89
93
94
90
3-(16-Benzyloxy-hexadec-1-enyl)-4,5-dimethoxy-1-(4-
methoxy-benzenesulfonyl)-1H-indole (11f, n ) 16). Yield:
81%. 1H NMR (300 MHz): δ 1.25 (s br, 20H, H-12 to 21), 1.47
(m, 2H, H-22), 1.58 (m, 2H, H-11), 2.30 (q, J ) 6.9 Hz, 2H,
H-10), 3.46 (t, J ) 6.6 Hz, 2H, H-23), 3.79 (s, 3H, -OCH3),
3.82 (s, 3H, -OCH3), 3.87 (s, 3H, -OCH3), 4.50 (s, 2H, H-24),
5.73 (dt, J ) 11.6 Hz, J ) 6.9 Hz, 1H, H-9), 6.74 (d, J ) 11.6
Hz, 1H, H-8), 6.86 (d, J ) 8.9 Hz, 2H, H-3′′,5′′), 6.95 (d, J )
8.9 Hz, 1H, H-6), 7.28-7.36 (m, 6H, H-2, 2′′′ to 6′′′), 7.65 (d, J
) 8.9 Hz, 1H, H-7), 7.78 (d, J ) 8.9 Hz, 2H, H-2′′,6′′). 13C NMR
(75 MHz): δ 26.2 (C-10), 29.5-29.7 (C-11 to 22), 55.6 (-OCH3),
57.1 (-OCH3), 61.3 (-OCH3), 70.5 (C-23), 72.8 (C-24), 109.0
(C-3,6), 111.9 (C-7), 114.4 (C-3′′,5′′), 119.7 (C-2), 124.3 (C-3′),
127.4-129.3 (C-7′,8,2′′,6′′,2′′′ to 6′′′), 130.8 (C-1′′), 133.3 (C-9),
138.7 (C-1′′′), 143.0 (C-4), 148.6 (C-5), 163.7 (C-4′′).
3-(16-Benzyloxy-hexadec-1-enyl)-5,6-dimethoxy-1-(4-
methoxy-benzenesulfonyl)-1H-indole (11g, n ) 16). Yield:
49%. 1H NMR (300 MHz): δ 1.26 (s br, 20H, H-12 to 21), 1.48
(m, 2H, H-22), 1.61 (m, 2H, H-11), 2.29 (q, J ) 6.9 Hz, 2H,
H-10), 3.46 (t, J ) 6.6 Hz, 2H, H-23), 3.78 (s, 3H, -OCH3),
3.89 (s, 3H, -OCH3), 3.97 (s, 3H, -OCH3), 4.50 (s, 2H, H-24),
5.79 (dt, J ) 11.3 Hz, J ) 6.9 Hz, 1H, H-9), 6.32 (d, J ) 11.3
Hz, 1H, H-8), 6.85 (d, J ) 8.9 Hz, 2H, H-3′′,5′′), 6.90 (s, 1H,
H-7), 7.25-7.35 (m, 6H, H-2, H-2′′′ to 6′′′), 7.55 (s, 1H, H-4),
7.77 (d, J ) 8.9 Hz, 2H, H-2′′,6′′). 13C NMR (75 MHz): δ 26.2
(C-10), 29.4-29.7 (C-11 to 22), 55.6 (-OCH3), 56.1, 56.4
10-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-yl]decan-
1-ol (12a, n ) 10). Yield: 92%. 1H NMR (200 MHz): δ 1.29 (s
br, 12H, H-10 to 15), 1.62 (m, 4H, H-9,16), 2.63 (t, J ) 7.4 Hz,
2H, H-8), 3.64 (t, J ) 6.4 Hz, 2H, H-17), 3.77 (s, 3H, -OCH3),
6.85 (d, J ) 9.1 Hz, 2H, H-3′′,5′′), 7.21-7.33 (m, 3H, H-2,5,6),
7.47 (d, J ) 6.9 Hz, 1H, H-4), 7.78 (d, J ) 9.1 Hz, 2H, H-2′′,6′′),
7.97 (d, J ) 7.6 Hz, 1H, H-7). 13C NMR (50 MHz): δ 24.9 (C-
15), 25.8 (C-9), 28.9 (C-8), 29.7 (C-10 to 14), 32.8 (C-16), 55.6
(-OCH3), 63.1 (C-17), 113.8 (C-7), 114.4 (C-9), 119.6 (C-3′′,5′′),
122.7 (C-4), 122.9 (C-6), 123.7 (C-3), 124.5 (C-5), 129.0 (C-
2′′,6′′), 131.3 (C-7′), 134.9 (C-1′′), 135.4 (C-2), 163.6 (C-4′′).
10-[5-Methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-
3-yl]decan-1-ol (12c, n ) 10). Yield: 91%. 1H NMR (200
MHz): δ 1.29 (s br, 12H, H-10 to 15), 1.60 (m, 4H, H-9,16),
2.58 (t, J ) 7.4 Hz, 2H, H-8), 3.64 (t, J ) 6.4 Hz, 2H, H-17),
3.77 (s, 3H, -OCH3), 3.82 (s, 3H, -OCH3), 6.83 (d, J ) 8.9
Hz, 2H, H-3′′,5′′), 6.88-6.93 (m, 2H, H-4,6), 7.24 (s, 1H, H-2),
7.75 (d, J ) 8.9 Hz, 2H, H-2′′,6′′), 7.86 (d, J ) 9.6 Hz, 1H,
H-7). 13C NMR (50 MHz): δ 24.9 (C-15), 25.8 (C-9), 28.7 (C-8),
29.4-29.6 (C-10 to 14), 32.9 (C-16), 55.6, 55.8 (-OCH3), 63.1
(C-17), 102.3 (C-4), 113.2 (C-6), 114.3 (C-3′′,5′′), 114.7 (C-7),
123.6 (C-2), 124.0 (C-3), 128.9 (C-2′′,6′′), 129.9 (C-7′), 130.2 (C-
3′), 132.4 (C-1′′), 156.3 (C-5), 163.6 (C-4′′).
10-[6-Methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-
3-yl]decan-1-ol (12d, n ) 10). Yield: 80%. 1H NMR (300