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7.29 (m, 1H, Ar), 6.61 (brs, 1H, NH), 3.68 (m, 4H,
CH2), 3.34 (s, 2H, CH2); 13C NMR (DMSO-d6): d
168.8, 155.7, 148.6, 135.2, 128.5, 116.5, 114.7, 113.2, 47.3,
44.8, 38.2. ESIMS: (m/z): 279.0 [M+Na]+, 257.0 [M+1]+.
115.3, 112.8, 51.3, 44.7, 41.8, 35.5, 34.2, 30.4, 24.6.
ESIMS: (m/z): 337.1 [M+2+Na]+, 336.1 [M+1+Na]+,
335.1 [M+Na]+, 315.1 [M+3]+, 314.1 [M+2]+, 213.1
[M+1]+.
4.3.3. 5-{3-[3-(2-Chloroethyl)ureido]phenyl}pentanoic acid
(4e). Compound 4e was synthesized from 13e. The crude
product was purified by flash chromatography (CH2Cl2/
EtOH (95/5)). Yield: 37%; IR (NaCl): m 3274, 1651,
4.3.8. 6-{3-[3-(2-Chloroethyl)ureido]phenyl}hexanoic acid
methyl ester (5f). Compound 5f was synthesized from
14f. The crude product was purified by flash chromato-
graphy (CH2Cl2/EtOH (97/3)). Yield: 32%; IR (NaCl): m
1
1593, 1244 cmꢁ1
;
1H NMR (acetone-d6): d 7.57 (brs,
3323, 1702, 1631, 1251 cmꢁ1; H NMR (CDCl3): d 8.11
1H, NH), 7.36 (m, 2H, Ar), 7.07 (m, 1H, Ar), 6.87 (d,
1H, J = 7.0, Ar), 6.74 (brs, 1H, NH), 3.66 (m, 4H,
CH2), 3.46 (m, 4H, CH2), 2.59 (m, 2H, CH2), 1.63 (m,
2H, CH2); 13C NMR (acetone-d6): d 174.6, 155.1,
143.7, 129.2, 123.9, 122.2, 118.9, 116.2, 49.7, 44.6,
41.2, 36.1, 30.2, 29.8. ESIMS: (m/z): 297.1 [Mꢁ1]+.
(brs, 1H, NH), 7,48 (m, 2H, Ar), 6.51 (m, 2H, Ar), 6.38
(brs, 1H, NH), 3.81 (s, 3H, CH3), 3.57 (m, 6H, CH2),
2.51 (m, 2H, CH2), 2.17 (m, 4H, CH2), 1.78 (m, 2H,
CH2); 13C NMR (CDCl3): d 174.1, 155.3, 138.3, 131.7,
129.3, 124.2, 121.1, 116.8, 51.4, 44.6, 41.9, 35.9, 34.1,
32.6, 30.8, 23.6. ESIMS: (m/z): 351.1 [M+2+Na]+,
350.1 [M+1+Na]+, 349.1 [M+Na]+, 329.1 [M+3]+,
328.2 [M+2]+, 227.1 [M+1]+.
4.3.4. 6-{3-[3-(2-Chloroethyl)ureido]phenyl}hexanoic acid
(4f). Compound 4f was synthesized from 13f. The crude
product was purified by flash chromatography (CH2Cl2/
EtOH (90/10)). Yield: 31%; mp 128–130 ꢁC; IR (KBr): m
4.3.9. 3-[3-(2-Chloroethyl)ureido]benzoic acid ethyl ester
(6a). Compound 6a was synthesized from 15a. The
crude product was purified by flash chromatography
(CH2Cl2/EtOH (98/2)). Yield: 88%; mp 128–130 ꢁC; IR
1
3306, 1690, 1633, 1241 cmꢁ1; H NMR (acetone-d6): d
8.17 (brs, 1H, NH), 7.31 (m, 1H Ar), 7.12 (m, 2H,
Ar), 6.79 (d, 1H, J = 7,5, Ar), 6.23 (brs, 1H, NH), 3.64
(m, 2H, CH2), 3.54 (m, 2H, CH2), 2.55 (m, 2H, CH2),
2.20 (m, 2H, CH2), 1.71 (m, 4H, CH2), 1.22 (m, 2H,
CH2); 13C NMR (acetone-d6): d 174.1, 156.1, 143.9,
141.1, 129.2, 122.6, 119.2, 116.8, 44.9, 42.5, 36.3, 34.1, 31.8,
30.6, 25.4. ESIMS: (m/z): 335.1 [M+Na]+, 313.1 [M+1]+.
(KBr): m 3335, 1730, 1642, 1238 cmꢁ1
;
1H NMR
(CDCl3): d 8.22 (brs, 1H, NH), 7.93 (s, 1H, Ar), 7.63
(d, 1H, J = 8.0, Ar), 7.57 (d, 1H, J = 7.0, Ar), 7.30 (m,
1H, Ar), 6.35 (brs, 1H, NH), 4.31 (q, 2H, J = 7.0,
CH2), 3.57 (m, 4H, CH2), 1.34 (t, 3H, J = 7.0, CH3);
13C NMR (CDCl3): d 166.7, 156.0, 139.1, 131.0, 129.1,
124.3, 124.1, 120.5, 61.2, 44.5, 42.0, 14.2. ESIMS: (m/z):
293.0 [M+Na]+, 271.0 [M+1]+.
4.3.5. 3-[3-(2-Chloroethyl)ureido]benzoic acid methyl
ester (5a). Compound 5a was synthesized from 14a.
The crude product was purified by flash chromatogra-
phy (CH2Cl2/EtOH (98/2)). Yield: 77%; mp 103–
4.3.10. 3-[3-(2-Chloroethyl)ureido]phenyl acetic acid ethyl
ester (6b). Compound 6b was synthesized from 15b. The
crude product was purified by flash chromatography
(CH2Cl2/EtOH (98/2)). Yield: 52%; mp 95–97 ꢁC; IR
105 ꢁC; IR (KBr): m 3309, 1709,1638, 1235 cmꢁ1
;
1H
NMR (CDCl3): d 8.21 (brs, 1H, NH), 7.87 (s, 1H, Ar),
7.61 (d, 1H, J = 7,0, Ar), 7.58 (d, 1H, J = 7,0, Ar),
7.21 (m, 1H, Ar), 5.89 (brs, 1H, NH), 3.76 (s, 3H,
CH3), 3.57 (m, 4H, CH2); 13C NMR (CDCl3): d 167.1,
156.2, 139.3, 131.1, 129.0, 125.0, 123.9, 120.4, 52.2,
46.4, 42.0. ESIMS: (m/z): 257.0 [M+1]+.
(KBr): m 3341, 1727, 1595, 1230 cmꢁ1
;
1H NMR
(CDCl3): d 7.89 (brs, NH, 1H), 7.17 (s, 1H, Ar), 7.08
(m, 2H, Ar), 6.81 (d, 1H, J = 8.0, Ar), 6.54 (brs, 1H,
NH), 4.09 (q, 2H, J = 7,0, CH2), 3.46 (m, 6H, CH2),
1.21 (t, 3H, J = 7,0, CH3); 13C NMR (CDCl3): d
172.1, 156.2, 139.2, 134.9, 129.7, 123.8, 120.8, 118.6,
61.1, 44.4, 42.0, 41.8, 14.1. ESIMS: (m/z): 307.0
[M+Na]+, 285.0 [M+1]+.
4.3.6. 3-[3-(2-Chloroethyl)ureido]phenyl acetic acid methyl
ester (5b). Compound 5b was synthesized from 14b. The
crude product was purified by flash chromatography
(CH2Cl2/EtOH (98/2)). Yield: 61%; mp 96–97 ꢁC; IR
4.3.11. 5-{3-[3-(2-Chloroethyl)ureido]phenyl}pentanoic acid
ethyl ester (6e). Compound 6e was synthesized from
15e. The crude product was purified by flash chroma-
tography (hexanes/ethyl acetate (6/4)). Yield: 87%; mp
(KBr): m 3330, 1732, 1650, 1234 cmꢁ1
;
1H NMR
(CDCl3): d 7.57 (brs, 1H, NH), 7.21 (m, 3H, Ar), 6.79
(m, 1H, Ar), 5.91 (brs, 1H, NH), 3.57 (m, 9H, CH2,
CH3); 13C NMR (CDCl3): d 172.5, 156.0, 139.1, 134.7,
129.2, 124.0, 120.9, 118.8, 52.1, 44.4, 40.9, 40.3. ESIMS:
(m/z): 293.0 [M+Na]+, 271.0 [M+1]+.
> 310 ꢁC; IR (KBr): m 3311, 1728, 1636, 1184 cmꢁ1
;
1H NMR (CDCl3): d 7.23 (m, 4H, Ar, NH), 6.89
(m, 1H, Ar), 5.63 (brs, 1H, NH), 4.31 (q, 2H,
J = 7.0, CH2), 3.63 (m, 4H, CH2), 2.56 (m, 2H,
CH2), 2.39 (m, 2H, CH2), 1.81 (m, 4H, CH2), 1.23
(t, 3H, J = 7.0, CH3); 13C NMR (CDCl3): d 175.1,
155.8, 143.6, 138.3, 129.3, 124.2, 121.1, 118.6, 60.3,
44.8, 42.0, 35.5, 34.2, 30.9, 25.3, 14.2. ESIMS: (m/z):
349.1 [M+Na]+, 327.1 [M+1]+.
4.3.7. 5-{3-[3-(2-Chloroethyl)ureido]phenyl}pentanoic acid
methyl ester (5e). Compound 5e was synthesized from
14e. The crude product was purified by flash chromato-
graphy (CH2Cl2/EtOH (97/3)). Yield: 19%; IR (NaCl): m
1
3326, 1702,1629, 1212 cmꢁ1; H NMR (CDCl3): d 8.21
(brs, 1 H, NH), 7.07 (m, 1H Ar), 6.57 (m, 3H, Ar),
6.17 (brs, 1H, NH), 3.66, (s, 3H, CH3), 3.51 (m, 4H,
CH2), 2.58 (m, 2H, CH2), 2.33 (t, 2H, J = 7.0, CH2),
1.65 (m, 2H, CH2), 1.25 (m, 2H, CH2); 13C NMR
(CDCl3): d 174.1, 155.3, 146.3, 143.4, 129.2, 118.8,
4.3.12. 6-{3-[3-(2-Chloroethyl)ureido]phenyl}hexanoic acid
ethyl ester (6f). Compound 6f was synthesized from 15f.
The crude product was purified by flash chromatogra-
phy (CH2Cl2/EtOH (98/2)). Yield: 81%; mp 72–74 ꢁC;