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4.32.1. 4-[(5-Chloro-2-{[(4-chlorophenyl)sulfonyl]ami-
no}phenoxy)methyl]benzoic acid (11). Yield 97%; TLC
Rf = 0.43 (MeOH/CHCl3, 3:17); 1H NMR (200
MHz, DMSO-d6) d 9.89 (br s, 1H), 7.93 (d, J = 8.0
Hz, 2H), 7.60 (d, J = 8.5Hz, 2H), 7.42 (d, J = 8.5 Hz,
2H), 7.34 (d, J = 8.0 Hz, 2H), 7.29 (d, J = 8.0 Hz,
1H), 7.06 (d, J = 2.0 Hz, 1H), 7.01 (dd, J = 8.0,
2.0 Hz, 1H), 4.98 (s, 2H); IR (KBr) 3331, 2877,
1689, 1595, 1498, 1424, 1395, 1353, 1252, 1172,
1123, 1095 cmꢀ1; MS (APCI, Neg.) m/e 450 (MꢀH)ꢀ.
4.32.7. 4-({4-Methyl-2-[(phenylsulfonyl)amino]phenolxy}-
methyl)benzoic acid (19). Yield 82%; TLC Rf = 0.43
(EtOAc/hexane/AcOH, 7:12:1); 1H NMR (200 MHz,
DMSO-d6) d 7.89 (d, J = 8.0 Hz, 2H), 7.66 (d, J =
7.0 Hz, 2H), 7.60–7.48 (m, 1H), 7.41 (d, J = 8.0 Hz, 2H),
7.35 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 2.0 Hz, 1H), 6.90
(dd, J = 8.0, 2.0 Hz, 1H), 6.76 (d, J = 8.0 Hz, 1H), 4.88 (s,
2H), 2.19 (s, 3H); IR (KBr) 3289, 2919, 1687, 1615, 1579,
1511, 1458, 1424, 1390, 1335, 1295, 1222, 1175, 1127,
1092, 1035, 1018 cmꢀ1; MS (FAB, Pos.) m/e 398 (M+H)+.
4.32.2.
4-({5-Chloro-2-[(phenylsulfonyl)amino]pheno-
4.32.8.
4-{[2-[Ethyl(phenylsulfonyl)amino]-5-(trifluoro-
lxy}methyl)benzoic acid (12). Yield 89%; TLC Rf = 0.39
(MeOH/CHCl3, 1:4); 1H NMR (200 MHz, DMSO-d6) d
12.98 (s, 1H), 9.78 (s, 1H), 7.92 (d, J = 8.0 Hz, 2H), 7.65
(d, J = 8.5 Hz, 2H), 7.55 (t, J = 8.5 Hz, 1H), 7.41 (t,
J = 8.5 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 7.28 (d,
J = 8.5 Hz, 1H), 7.04 (d, J = 2.0 Hz, 1H), 6.98 (dd,
J = 8.5, 2.0 Hz, 1H), 4.98 (s, 2H); IR (KBr) 3260, 2996,
methyl)phenoxy]methyl}benzoic acid (20). Yield 76%;
TLC Rf = 0.43 (MeOH/CHCl3, 1:9); 1H NMR
(200 MHz, CDCl3) d 8.09 (d, J = 7.4 Hz, 2H), 7.70–
7.60 (m, 2H), 7.50–7.20 (m, 7H), 7.15 (d, J = 1.6 Hz,
1H), 4.94 (s, 2H), 3.69 (q, J = 7.4 Hz, 2H), 1.11 (t,
J = 7.4 Hz, 3H); IR (KBr) 2981, 2360, 1694, 1614,
1510, 1429, 1332, 1219, 1172, 1127, 1087, 1019 cmꢀ1
;
2887, 1687, 1598, 1426, 1339, 1290, 1265, 1168 cmꢀ1
;
MS (FAB, Pos.) m/e 480 (M+H)+.
MS (APCI, Neg.) m/e 416 (MꢀH)ꢀ.
4.32.9. {[2-[(Phenylsulfonyl)(propyl)amino]-5-(trifluoro-
methyl)phenoxy]methyl}benzoic acid (21). Yield 70%;
TLC Rf = 0.50 (MeOH/CHCl3, 1:9); 1H NMR
(200 MHz, CDCl3) d 8.09 (d, J = 8.2 Hz, 2H), 7.70–
7.60 (m, 2H), 7.50–7.20 (m, 7H), 7.14 (s, 1H), 4.92 (s,
2H), 3.59 (t, J = 7.4 Hz, 2H), 1.60–1.40 (m, 2H), 0.88
(t, J = 7.4 Hz, 3H); IR (KBr) 2970, 1694, 1614,
150,1428, 1332, 1171, 1127, 1087, 1018 cmꢀ1; MS
(FAB, Pos.) m/e 494 (M+H)+.
4.32.3.
4-({5-Fluoro-2-[(phenylsulfonyl)amino]pheno-
lxy}methyl)benzoic acid (15). Yield 85%; TLC Rf = 0.42
(EtOAc/hexane/AcOH, 6:13:1); 1H NMR (200 MHz,
DMSO-d6) d 12.95 (br s, 1H), 9.65 (br s, 1H), 7.91 (d,
J = 8.5 Hz, 2H), 7.60 (d, J = 7.0 Hz, 2H), 7.52 (t,
J = 7.0 Hz, 1H), 7.39 (d, J = 7.5 Hz, 2H), 7.35 (d,
J = 7.5 Hz, 2H), 7.26 (dd, J = 7.0, 6.5 Hz, 1H), 6.84
(dd, J = 11.0, 2.5 Hz, 1H), 6.75 (dt, J = 8.5, 2.5 Hz,
1H), 4.90 (s, 2H); IR (KBr) 3267, 1686, 1616, 1459,
1449, 1398, 1336, 1284, 1163, 1093, 1041, 1019 cmꢀ1
;
4.32.10. {[2-[Isopropyl(phenylsulfonyl)amino]-5-(trifluoro-
methyl)phenoxy]methyl}benzoic acid (22). Yield 78%; TC
Rf = 0.44 (MeOH/CHCl3/AcOH, 5:100:1); 1H NMR
(200 MHz, CDCl3) d 8.15 (d, J = 8.6 Hz, 2H), 7.81 (m,
2H), 7.52 (m, 3H), 7.38 (m, 2H), 7.24 (m 3H), 5.13 (s, 2H),
4.4 0 (sept, J = 6.8 Hz, 1H9, 1.06 (d, J = 6.8 Hz, 6H); IR
(KBr) 3423, 2982, 1698, 1426, 1332, 1294, 1218, 1172, 1127,
1088, 1034 cmꢀ1, MS (FAB, Pos.) m/e 494 (M+H)+, 353.
MS (FAB, Pos.) m/e 402 (M+H)+.
4.32.4. 4-({5-Methyl-2-[(phenylsulfonyl)amino]phenolxy}-
methyl)benzoic acid (16). Yield 86%; TLC Rf = 0.43
(EtOAc/hexane/AcOH, 7:12:1); 1H NMR (200 MHz,
DMSO-d6) d 7.91 (d, J = 8.5 Hz, 2H), 7.62 (d, J =
7.0 Hz, 2H), 7.57–7.45 (m, 1H), 7.44–7.30 (m, 4H),
7.14 (d, J = 8.0 Hz, 1H), 6.75 (s, 2H), 6.71 (d,
J = 8.0 Hz, 1H), 4.89 (s, 2H), 2.21 (s, 3H); IR (KBr)
3266, 2867, 1685, 1614, 1579, 1510, 1449, 1415, 1337,
1286, 1160, 1122, 1093, 1048, 1020 cmꢀ1; MS (FAB,
Pos.) m/e 398 (M+H)+.
4.32.11. {[2-[Isobutyl(phenylsulfonyl)amino]-5-(trifluoro-
methyl)phenoxy]methyl}benzoic acid (23). Yield 80%;
TLC Rf = 0.53 (MeOH/CHCl3, 1:9); 1H NMR
(200 MHz, CDCl3) d 8.10 (d, J = 8.4 Hz, 2H), 7.70–
7.60 (m, 2H), 7.50–7.20 (m, 7H), 7.11 (d, J = 1.6 Hz,
1H), 5.00–4.80 (m, 2H), 3.44 (d, J = 7.4 Hz, 2H), 1.70–
1.50 (m, 1H), 0.90 (d, J = 6.6 Hz, 6H); IR (KBr) 2963,
1694, 1510, 1448, 1427, 1331, 1289, 1257, 1213, 1169,
1127, 1086, 1019 cmꢀ1; MS (FAB, Pos.) m/e 508 (M+H)+.
4.32.5. 4-({5-Methoxy-2-[(phenylsulfonyl)amino]phenolxy}-
methyl)benzoic acid (17). Yield 89%; TLC Rf = 0.40
1
(MeOH/CHCl3, 1:4); H NMR (200 MHz, DMSO-d6) d
7.90 (d, J = 8.5 Hz, 2H), 7.59 (d, J = 8.0 Hz, 1H), 7.51
(t, J = 8.0 Hz, 1H), 7.44–7.28 (m, 4H), 7.15 (d, J = 8.5
Hz, 1H), 6.54–6.47 (m, 2H), 4.86 (s, 2H), 3.69 (s, 3H);
IR (KBr) 3293, 3006, 1686, 1614, 1510, 1450, 1398, 1337,
1200, 1166 cmꢀ1; MS (APCI, Neg.) m/e 412 (MꢀH)ꢀ.
4.32.12. {[2-[Neopentyl (phenylsulfonyl)amino]-5-(trifluo-
romethyl)phenoxy]methyl}benzoic acid (24). Yield 80%;
TLC Rf = 0.50 (MeOH/CHCl3, 1:9); 1H NMR
(200 MHz, CDCl3) d 8.12 (d, J = 8.0 Hz, 2H), 7.60–7.40
(m, 4H), 7.40–7.20 (m, 5H), 7.09 (d, J = 1.8 Hz, 1H),
5.02 (d, J = 12.4 Hz, 1H), 4.72 (d, J = 12.4 Hz, 1H), 3.53
8s, 2H), 0.86 (s, 9H); IR (KBr) 2961, 1694, 1614, 1581,
1510, 1478, 1448, 1427, 1329, 1279, 1234, 1201, 1168,
1129, 100, 1019 cmꢀ1; MS (EI, Pos.) m/e 521 (M+).
4.32.6.
4-{[2-[(Phenylsulfonyl)amino]-5-(trifluorometh-
yl)phenoxy]methyl}benzoic acid (18). Yield 99%; TLC
Rf = 0.52 (MeOH/CHCl3/AcOH, 5:100:1); 1H NMR
(200 MHz, DMSO-d6) d 12.95 (s, 1H), 10.10 (br s,
1H), 7.93 (d, J = 8.0 Hz, 2H), 7.75 (m, 2H), 7.59 (m,
1H), 7.53–7.40 (m, 5H), 7.27 (m, 2H), 5.14 (s, 2H); IR
(KBr) 3379, 3297, 3072, 2671, 1694, 1415, 1522, 1443,
1353, 1334, 1286, 1169, 1123, 1090, 1011 cmꢀ1; MS
(FAB, Pos.) m/e 452 (M+H)+.
4.32.13. {[2-[(Cyclopentylmethyl)(phenylsulfonyl)amino]-
5-(trifluoromethyl)phenoxy]methyl}benzoic acid (25).
Yield 100%; TLC Rf = 0.40 (MeOH/CHCl3/H2O,