5.6 Hz), 3.70 (2H, s), 2.35 (3H, s), 2.24 (2H, m); 13C NMR (100
MHz, CDCl3 + CD3OD) δ 174.8, 153.2, 153.0, 152.9, 137.6,
134.1, 131.4, 129.1, 127.6, 124.0, 115.8, 115.4, 112.6, 111.9,
107.7, 101.8, 70.6, 65.4, 65.3, 31.0, 29.5, 21.0; IR (KBr) 3454,
2933, 2880, 1509, 1241, 1193, 1066, 824 cm-1; HRMS-ESI
[M+H]+ calcd for C27H27NO5: 446.1962, found: 446.1976.
155.2, 137.5, 137.1, 133.9, 129.7, 128.9, 127.4, 122.2, 121.9,
118.9, 109.4, 107.8, 107.0, 101.7, 95.6, 69.8, 64.9, 64.5, 48.0,
29.2, 20.5; IR (neat) 3357, 2918, 1694, 1601, 1458, 1260, 1176,
1152, 1063, 804 cm-1; HRMS-ESI [M+H]+ calcd for C27H27NO5:
446.1962, found: 446.1967.
(6-{3-[3-(4-Chlorobenzyloxy)phenoxy]propoxy}-1H-indol-3-
yl)acetic acid (58): Ivory solid; Rf=0.13 (CHCl3/MeOH 8:1); 1H
NMR (400 MHz, CD3OD) δ 7.33-7.41 (5H, m), 7.14 (1H, t, J =
8.0 Hz), 7.03 (1H, s), 6.90 (1H, d, J = 2.0 Hz), 6.71 (1H, dd, J =
8.4, 2.0 Hz), 6.54-6.56 (3H, s), 4.99 (2H, s), 4.15 (4H, dd, J =
6.4, 6.0 Hz), 3.67 (2H, s), 2.21 (2H, m); 13C NMR (100 MHz,
CD3OD + CDCl3) δ175.4, 160.1, 159.6, 155.3, 137.0, 135.5,
133.5, 129.8, 128.7, 128.5, 122.3, 121.9, 119.1, 109.5, 107.7,
107.3, 107.0, 101.8, 95.7, 69.1, 64.9, 64.6, 31.3, 29.2; IR (neat)
3363, 2955, 2925, 1694, 1603, 1493, 1262, 1180 cm-1; HRMS-
ESI [M+H]+ calcd for C26H24ClNO5: 466.1416, found: 466.1426.
(5-{3-[4-(4-Chlorobenzyloxy)phenoxy]propoxy}-1H-indol-3-
yl)acetic acid (53): White solid; Rf=0.29 (CHCl3/MeOH 8:1); 1H
NMR (400 MHz, CDCl3 + CD3OD) δ 7.38 (2H, d, J = 8.4 Hz),
7.34 (2H, d, J = 8.4 Hz), 7.26 (1H, d, J = 8.8 Hz), 7.16 (1H, s),
7.09 (1H, s), 6.89 (4H, s), 6.83 (1H, d, J = 8.8 Hz), 5.00 (2H, s),
4.21 (2H, t, J = 6.0 Hz), 4.16 (2H, t, J = 6.0 Hz), 3.71 (2H, s),
2.25 (2H, m); 13C NMR (100 MHz, CDCl3 + CD3OD) δ 174.9,
153.3, 152.8, 152.5, 135.7, 133.4, 131.5, 128.7, 128.5, 127.4,
124.1, 115.8, 115.4, 112.3, 111.9, 107.4, 101.7, 69.8, 65.3, 65.2,
31.0, 29.4; IR (KBr) 3451, 2930, 2882, 1728, 1509, 1241, 1195
cm-1; HRMS-ESI [M+H]+ calcd for C26H24ClNO5: 466.1416,
found: 466.1416.
(1-Benzyl-6-{3-[3-(4-methylbenzyloxy)phenoxy]propoxy}-1H-
indol-3-yl)acetic acid (59): Ivory solid; Rf=0.33 (CHCl3/MeOH
1
(1-Benzyl-5-{3-[4-(4-methylbenzyloxy)phenoxy]propoxy}-1H-
indol-3-yl)acetic acid (54): White solid; Rf=0.48 (CHCl3/MeOH
8:1); H NMR (400 MHz, CDCl3) δ 7.47 (1H, d, J = 8.8 Hz),
7.24-7.31 (5H, m), 7.09-7.19 (5H, m), 6.98 (1H, s), 6.80 (1H, dd,
J = 8.8, 2.0 Hz), 6.73 (1H, d, J = 2.0 Hz), 6.50-6.57 (3H, m), 5.19
(2H, s), 4.97 (2H, s), 4.12 (4H, t, J = 6.0 Hz), 3.76 (2H, s), 2.35
(3H, s), 2.22 (2H, m); 13C NMR (100 MHz, CDCl3) δ 176.9,
160.1, 155.8, 137.7, 137.3, 133.9, 129.8, 129.2, 128.8, 127.6,
126.8, 126.2, 119.7, 109.9, 107.1, 101.8, 94.5, 69.9, 65.1, 64.5,
49.9, 31.0, 29.3, 21.2; IR (KBr) 3431, 2922, 1715, 1620, 1493,
1232, 1182, 1157 cm-1; HRMS-ESI [M+H]+ calcd for
C34H33NO5: 536.2431, found: 536.2441.
1
8:1); H NMR (400 MHz, CDCl3) δ 7.34 (2H, d, J = 4.0 Hz),
7.28 (2H, d, J = 7.2 Hz), 7.15-7.23 (5H, m), 7.11 (2H, s), 6.99
(2H, d, J = 4.0 Hz), 6.84 (2H, d, J = 8.8 Hz), 6.79 (2H, d, J = 8.8
Hz), 6.77-6.80 (1H, m), 5.06 (2H, s), 4.91 (2H, s), 4.08 (2H, t,
J = 5.6 Hz), 4.04 (2H, t, J = 6.0 Hz), 3.65 (2H, s), 2.33 (3H, s),
2.16 (2H, m); 13C NMR (100 MHz, CDCl3) δ 153.2, 153.0,
137.6, 134.2, 131.8, 129.2, 128.7, 128.5, 128.0, 127.6, 127.0,
126.7, 115.8, 115.4, 112.6, 102.0, 70.6, 65.3, 65.3, 50.1, 39.3,
29.5, 21.2; IR (KBr) 3427, 3029, 2931, 1701, 1509, 1230 cm-1;
HRMS-ESI [M+H]+ calcd for C34H33NO5: 536.2431, found:
536.2451.
(1-Benzyl-6-{3-[3-(4-chlorobenzyloxy)phenoxy]propoxy}-1H-
indol-3-yl)acetic acid (60): Ivory solid; Rf=0.27 (CHCl3/MeOH
1
8:1); H NMR (400 MHz, CDCl3) δ 7.44 (1H, d, J = 8.4 Hz),
(1-Benzyl-5-{3-[4-(4-chlorobenzyloxy)phenoxy]propoxy}-1H-
indol-3-yl)acetic acid (55): White solid; Rf=0.52 (CHCl3/MeOH
8:1); H NMR (400 MHz, CDCl3) δ 7.36 (1H, d, J = 8.4 Hz),
7.33 (4H, s), 7.21-7.25 (3H, m), 7.15 (1H, dd, J = 9.2, 7.6 Hz),
7.06 (2H, d, J = 6.8 Hz), 6.94 (1H, s), 6.77 (1H, d, J = 8.8 Hz),
6.69 (1H, s), 6.52-6.53 (3H, m), 5.13 (2H, s), 4.96 (2H, s) 4.11
(2H, t, J = 6.0 Hz), 4.09 (2H, t, J = 6.4 Hz), 3.71 (2H, s), 2.20
(2H, m); 13C NMR (100 MHz, CDCl3) δ 160.1, 159.7, 155.7,
137.3, 135.5, 129.9, 128.8, 128.7, 127.6, 126.8, 107.0, 101.8,
94.5, 69.1, 65.0, 64.6, 51.1, 29.3, 22.3; IR (KBr) 3427, 3030,
2925, 1716, 1618, 1493, 1232, 1181, 1156 cm-1; HRMS-ESI
[M+H]+ calcd for C33H30ClNO5: 556.1885, found: 556.1898.
1
7.32 (4H, s), 7.21-7.25 (3H, m), 7.01-7.07 (4H, m), 6.78-6.85
(5H, m), 5.11 (2H, s), 4.92 (2H, s), 4.12 (2H, dd, J = 6.0, 5.6 Hz),
4.06 (2H, dd, J = 6.0, 5.4 Hz), 3.68 (2H, s), 2.18 (2H, m); 13C
NMR (100 MHz, CDCl3) δ 153.4, 153.3, 152.6, 137.4, 135.8,
133.6, 128.8, 128.7, 127.5, 126.7, 115.8, 115.4, 112.6, 110.6,
105.0, 102.0, 69.9, 65.2, 52.0, 50.2, 29.5; IR (KBr) 3434, 3030,
2022, 2864, 1704, 1508, 1492, 1231 cm-1; HRMS-ESI [M+H]+
calcd for C33H30ClNO5: 556.1885, found: 556.1886.
{5-[3-(3-Phenoxyphenoxy)propoxy]-1H-indol-3-yl}acetic acid
1
(61): Brown liquid; Rf=0.29 (CHCl3/MeOH 8:1); H NMR (400
(6-{3-[2-(4-Methylbenzyloxy)phenoxy]propoxy}-1H-indol-3-
yl)acetic acid (56): White solid; Rf=0.24 (CHCl3/MeOH 8:1); 1H
NMR (400 MHz, CDCl3) δ 7.81 (NH, br s), 7.43 (1H, d, J = 8.4
Hz), 7.31 (2H, d, J = 8.0 Hz), 7.10 (2H, d, J = 8.0 Hz), 7.01 (1H,
d, J = 2.4 Hz), 6.78-6.96 (8H, m), 5.07 (2H, s), 4.23 (2H, t, J =
6.4 Hz), 4.20 (2H, t, J = 6.0 Hz), 3.75 (2H, s), 2.31 (3H, s), 2.31
(2H, m); 13C NMR (100 MHz, CDCl3) δ 176.6, 155.9, 149.2,
148.8, 137.4, 136.8, 134.4, 129.1, 127.3, 121.9, 121.7, 121.5,
121.3, 119.4, 115.2, 114.3, 110.5, 107.7, 95.6, 71.1, 65.9, 65.1,
29.4, 27.0, 21.1; IR (neat) 3398, 2955, 2873, 1710, 1630, 1503,
1254, 1171, 1123, 1052, 801 cm-1; HRMS-ESI [M+H]+ calcd for
C27H27NO5: 446.1962, found: 446.1970.
MHz, CDCl3) δ 7.97 (NH, br s), 7.31 (2H, dd, J = 8.4, 8.0 Hz),
7.21 (1H, d, J = 8.8 Hz), 7.20 (1H, dd, J = 8.4, 8.0 Hz), 7.00-7.11
(4H, m), 6.85 (1H, dd, J = 8.8, 2.4 Hz), 6.66 (1H, dd, J = 8.0, 2.4
Hz), 6.56-6.60 (2H, m), 4.17 (2H, t, J = 5.6 Hz), 4.13 (2H, t, J =
6.0 Hz), 3.73 (2H, s), 2.24 (2H, m); 13C NMR (100 MHz, CDCl3
+ CD3OD) δ 160.4, 158.5, 157.0, 152.7, 131.9, 129.9, 129.4,
127.6, 124.0, 123.1, 118.7, 112.0, 111.6, 110.5, 109.8, 107.4,
105.1, 101.5, 65.0, 64.5, 48.2, 48.0, 29.2; IR (neat) 3418, 2929,
1707, 1585, 1487, 1214, 1139 cm-1; HRMS-ESI [M+H]+ calcd for
C25H23NO5: 418.1649, found: 418.1649.
{5-[3-(3-p-Tolyloxyphenoxy)propoxy]-1H-indol-3-yl}acetic
acid (62): Pale yellow oil; Rf=0.13 (CHCl3/MeOH 8:1); 1H NMR
(400 MHz, CDCl3) δ 7.96 (NH, br s), 7.21 (1H, d, J = 8.8 Hz),
7.17 (1H, dd, J = 8.0, 7.6 Hz), 7.12 (2H, d, J = 8.4 Hz), 7.11-7.13
(1H, m), 6.82 (2H, d, J = 8.4 Hz), 6.85 (1H, d, J = 8.8 Hz), 6.63
(1H, dd, J = 8.0, 1.6 Hz), 6.53-6.56 (2H, m), 4.16 (2H, t, J = 6.0
Hz), 4.12 (2H, t, J = 6.0 Hz), 3.73 (3H, s), 2.32 (3H, s), 2.23 (2H,
m); 13C NMR (100 MHz, CDCl3) δ 160.2, 159.0, 153.4, 133.1,
131.3, 130.2, 130.0, 124.0, 119.3, 113.0, 112.0, 110.4, 109.0,
107.5, 104.9, 101.7, 100.0, 65.1, 64.7, 31.1, 29.4, 20.7; IR (neat)
(6-{3-[3-(4-Methylbenzyloxy)phenoxy]propoxy}-1H-indol-3-
yl)acetic acid (57): Ivory solid; Rf=0.17 (CHCl3/MeOH 8:1); 1H
NMR (400 MHz, CDCl3) δ 7.91 (NH, br s), 7.46 (1H, d, J = 8.4
Hz), 7.31 (2H, d, J = 8.0 Hz), 7.18 (2H, d, J = 8.0 Hz), 7.14-7.18
(1H, m), 7.06 (1H, s), 6.86 (1H, d, J = 2.0 Hz), 6.81 (1H, dd, J =
8.4, 2.0 Hz), 6.25~6.57 (3H, m), 4.98 (2H, s), 4.18 (2H, t, J = 6.0
Hz), 4.15 (2H, t, J = 6.0 Hz), 3.77 (2H, s), 2.35 (3H, s), 2.26 (2H,
m); 13C NMR (100 MHz, CDCl3 +CD3OD) δ 176.4, 160.1, 159.9,