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CH3); 13C NMR (68 MHz; d6-DMSO) dC 171.6 (C@O), 170.9 (C@O),
155.7 (C@O), 151.9 (Ar-C), 147.5 (Ar-C), 143.2 (Ar-C), 134.3 (Ar-
C), 131.1 (Ar-C), 127.8 (Ar-C), 121.9 (Ar-C), 119.1 (Ar-C), 115.3
(Ar-C), 112.5 (Ar-C), 108.5 (Ar-C), 102.0 (Ar-C), 101.4 (CH2O), 78.5
(C(CH3)3), 50.8 (CHCH3), 36.9 (CH2), 28.8 (C(CH3)3), 26.5 (CH2),
18.8 (CHCH3).
(C(CH3)3), 56.8 (CHNH), 52.7 (CH3), 50.7 (CHCH3), 35.4 (CH2), 28.6
(C(CH3)3), 26.5 (CH2), 18.8 (CHCH3).
7.1.4.1.7. 3-(5-Amino-2-hydroxyphenyl)-N-(4-pyridylmethyl)pro-
panamide; Boc
L-alanine derivative 16h. Compound 16h was syn-
thesized from compound 11h (0.27 g, 1.00 mmol), Boc-
L-alanine
(0.20 g, 1.05 mmol), N-methylmorpholine (0.10 g, 1.00 mmol) and
IBCF (0.14 g, 1.00 mmol) in dry THF/DMF (20 mL, 3:1). No further
purification was required. Yield: (0.30 g, 68%) as a pale pink pow-
der, mp 115–117 °C. LRMS (ES) for C23H30N4O5. Calculated mass
of molecular ion 465.50 [M+Na]+. Measured mass: 465.16; IR mmax
cmÀ1 3294, 3200–2550, 1644, 1505, 1232, 1193, 1111; 1H NMR
(400 MHz; d6-DMSO) dH 9.61 (1H, s, NH), 9.18 (1H, br, s, OH),
8.46–8.41 (3H, m, NHCH2, 2Â Ar-H), 7.31–7.26 (2H, m, Ar-H),
7.12 (2H, d, J = 6.0 Hz, Ar-H), 6.99 (1H, d, J = 7.3 Hz, NHCH), 6.71
(1H, d, J = 9.2 Hz, Ar-H), 4.27 (2H, d, J = 6.0 Hz, CH2NH), 4.07 (1H,
p, J = 6.9 Hz, CH), 2.75 (2H, t, J = 7.6 Hz, CH2), 2.44 (2H, t,
J = 7.8 Hz, CH2), 1.37 (9H, s, 3Â CH3), 1.22 (3H, d, J = 7.3 Hz, CHCH3);
13C NMR (101 MHz; d6-DMSO) dC 172.5 (C@O), 171.5 (C@O), 155.6
(C@O), 151.6 (Ar-C), 150.0 (2Â Ar-C), 149.1 (Ar-C), 131.3 (Ar-C),
127.7 (Ar-C), 122.5 (2Â Ar-C), 121.9 (Ar-C), 119.0 (Ar-C), 115.3
(Ar-C) 78.5 (C(CH3)3), 50.7 (CHCH3), 41.5 (CH2NH), 35.8 (CH2),
28.7 (C(CH3)3) 26.7 (CH2), 18.8 (CH3).
7.1.4.1.4. 3-(5-Amino-2-hydroxyphenyl)-N-(3,4-dimethoxyphenyl)
propanamide; Boc
L-alanine derivative 16d. Compound 16d was
synthesized from compound 11d (0.32 g, 1.00 mmol), Boc-
L
-ala-
nine (0.20 g, 1.05 mmol), N-methylmorpholine (0.10 g, 1.00 mmol)
and IBCF (0.14 g, 1.00 mmol) in dry THF (20 mL). No further purifi-
cation was required. Yield: (0.40 g, 81%) of light brown crystals, mp
86–88 °C. HRMS (NSI) for C25H33N3O7. Calculated mass of molecu-
lar ion 488.2391 [M+H]+. Measured mass: 488.2391; IR mmax cmÀ1
3281, 3250–2800, 1660, 1510, 1229, 1161, 1023; 1H NMR
(400 MHz; d6-DMSO) dH 9.77 (1H, s, NH), 9.61 (1H, s, br, OH),
9.21 (1H, s, NH), 7.36–7.23 (3H, m, Ar-H, NH), 7.08 (1H, dd,
J = 8.7 and 1.8 Hz, Ar-H), 6.98 (1H, d, J = 7.3 Hz, Ar-H), 6.86 (1H, d,
J = 8.7 Hz, Ar-H), 6.72 (1H, d, J = 8.7 Hz, Ar-H), 4.03 (1H, p,
J = 6.6 Hz, CH), 3.68 (2Â 3H, d, J = 4.6 Hz, 2Â CH3), 2.79 (2H, t,
J = 7.8 Hz, CH2), 2.51 (2H, m, CH2), 1.38 (9H, s, 3Â CH3), 1.22 (3H,
t, J = 6.9 Hz, CH3); 13C NMR (101 MHz; d6-DMSO) dC 171.6 (C@O),
170.8 (C@O), 155.6 (C@O), 151.6 (Ar-C), 149.0 (Ar-C), 145.1 (Ar-
C), 133.5 (Ar-C), 131.2 (Ar-C), 127.8 (Ar-C), 121.9 (Ar-C), 119.1
(Ar-C), 115.2 (Ar-C), 112.5 (Ar-C), 111.5 (Ar-C), 104.9 (Ar-C), 78.5
(C(CH3)3), 56.2 (CH3O), 55.8 (CH3O), 50.7 (CHCH3), 36.9 (CH2),
28.7 (C(CH3)3), 26.5 (CH2), 18.8 (CHCH3).
7.1.4.1.8. 3-(5-Amino-2-hydroxyphenyl)-N-(3-imidazol-1-ylpro-
pyl)propanamide; Boc
L-alanine derivative 16i. Compound 16i
was synthesized from compound 11i (0.29 g, 1.00 mmol), Boc-
L-
alanine (0.20 g, 1.05 mmol), N-methylmorpholine (0.10 g,
1.00 mmol) and IBCF (0.14 g, 1.00 mmol) in dry THF/DMF (20 mL,
1:1). No further purification was required. Yield: (0.35 g, 76%) of
an orange wax. LRMS (ES) for C23H33N5O5. Calculated mass of
molecular ion 460.54 [M+H]+. Measured mass: 460.24; IR mmax
cmÀ1 3241, 3200–2600, 1650, 1547, 1505, 1232, 1162, 745; 1H
NMR (400 MHz; d6-DMSO) dH 9.60 (1H, br, s, OH), 7.91 (1H, t,
J = 5.7 Hz, NHCH2), 7.60 (1H, s, Ar-H), 7.28 (1H, s, Ar-H), 7.23 (1H,
dd, J = 8.7 and 2.8 Hz, Ar-H), 7.15 (1H, s, Ar-H), 7.08 (1H, d,
J = 7.8 Hz, NH), 6.99 (1H, d, J = 7.3 Hz, NH), 6.88 (1H, s, Ar-H), 6.70
(1H, d, J = 8.7 Hz, Ar-H), 4.06 (1H, p, J = 7.1 Hz, CH), 3.89 (2H, t,
J = 6.9 Hz, CH2CH2CH2NH), 2.98 (2H, q, J = 6.4 Hz, CH2CH2CH2NH),
2.70 (2H, t, J = 7.8 Hz, CH2), 2.33 (2H, t, J = 7.8 Hz, CH2), 1.79 (2H,
p, J = 6.9 Hz, CH2CH2CH2NH) 1.38 (9H, s, 3Â CH3), 1.22 (3H, d,
J = 7.3 Hz, CH3); 13C NMR (101 MHz; d6-DMSO) dC 175.2 (C@O),
172.4 (C@O), 155.8 (C@O), 151.5 (Ar-C), 137.8 (Ar-C), 131.2 (Ar-
C), 128.8 (Ar-C), 127.9 (Ar-C), 121.8 (Ar-C), 119.9 (Ar-C), 119.0
(Ar-C), 115.3 (Ar-C), 78.4 (C(CH3)3), 50.7 (CHCH3), 44.1 (CH2),
36.1 (CH2), 36.0 (CH2), 31.2 (CH2), 28.7 (C(CH3)3), 26.6 (CH2), 18.8
(CH3).
7.1.4.1.9. Ethyl 3-(5-amino-2-hydroxyphenyl)propanoate; Boc b-
alanine derivative 17a. Compound 17a was synthesized from
compound 11a (0.21 g, 1.00 mmol), Boc-b-alanine (0.20 g,
1.05 mmol), N-methylmorpholine (0.10 g, 1.00 mmol) and IBCF
(0.14 g, 1.00 mmol) in dry THF (20 mL). No further purification
was required. Yield: (0.30 g, 79%) as a brown solid, mp 91–93 °C.
HRMS (NSI) for C19H28N2O6. Calculated mass of molecular ion
381.2020 [M+H]+. Measured mass: 381.2023; IR mmax cmÀ1 3296,
3163, 2982, 1734, 1687, 1549, 1440, 1364, 1284, 1247, 1161; 1H
NMR (400 MHz; d6-DMSO) dH 9.64 (1H, s, NH), 9.21 (1H, s, br,
OH), 7.27 (1H, d, J = 2.3 Hz, Ar-H), 7.29 (1H, dd, J = 8.7 and
2.52 Hz, Ar-H), 6.86 (1H, t, J = 5.7 Hz, NHCH2), 6.68 (1H, d,
J = 8.7 Hz, Ar-H), 4.04 (2H, q, J = 7.0 Hz, CH2CH3), 3.18 (2H, q,
J = 7.0 Hz, CH2NH), 2.72 (2H, m, CH2CH2CO), 2.52 (2H, m, CH2CO),
2.39 (2H, t, J = 7.1 Hz, CH2CH2NH), 1.38 (9H, s, 3Â CH3), 1.16 (3H,
t, J = 7.1 Hz, CH3); 13C NMR (101 MHz; d6-DMSO) dC 172.9 (C@O),
169.1 (C@O), 156.0 (C@O), 151.5 (Ar-C), 131.4 (Ar-C), 126.8 (Ar-
C), 121.8 (Ar-C), 119.2 (Ar-C), 115.1 (Ar-C), 78.1 (C(CH3)3), 60.3
(CH2CH3), 37.2 (CH2), 37.1 (CH2), 34.1 (CH2), 28.8 (C(CH3)3), 26.2
(CH2), 14.6 (CH3).
7.1.4.1.5. 3-(5-Amino-2-hydroxyphenyl)-N-(4-hydroxyphenyl)pro-
panamide; Boc
L-alanine derivative 16f. Compound 16f was syn-
thesized from compound 11f (0.60 g, 2.20 mmol), Boc-
L
-alanine
(0.44 g, 2.30 mmol), N-methylmorpholine (0.22 g, 2.20 mmol) and
IBCF (0.30 g, 2.20 mmol) in dry THF/DMF (25 mL, 4:1). No further
purification was required. Yield: (0.45 g, 46%) of a white powder,
mp 102–104 °C. LRMS (ES) for C23H29N3O6. Calculated mass of
molecular ion 466.48 [M+Na]+. Measured mass: 466.19; IR mmax
cmÀ1 3220, 3200–2470, 1651, 1510, 1227, 1112, 834; 1H NMR
(400 MHz; d6-DMSO) dH 9.65 (1H, s, NH), 9.60 (1H, s, NH), 9.19
(1H, s, br, OH), 9.15 (1H, br s, OH), 7.39–7.30 (3H, m, Ar-H), 7.25
(1H, dd, J = 8.5 and 2.5 Hz, Ar-H), 6.99 (1H, d, J = 7.3 Hz, NHCH),
6.72–6.65 (3H, m, Ar-H), 4.07 (1H, p, J = 6.9 Hz, CHNH), 2.78 (2H,
t, J = 7.8 Hz, CH2), 2.50 (2H, m, CH2), 1.38 (9H, s, 3Â CH3), 1.23
(3H, d, J = 6.9 Hz, CH3); 13C NMR (101 MHz; d6-DMSO) dH 171.6
(C@O), 170.5 (C@O), 155.6 (C@O), 153.6 (Ar-C), 151.6 (Ar-C),
131.5 (Ar-C), 131.2 (Ar-C), 127.9 (Ar-C), 121.9 (Ar-C), 121.5 (2Â
Ar-C), 119.0 (Ar-C), 115.5 (2Â Ar-C), 115.2 (Ar-C), 78.5 (C(CH3)3),
50.74 (CHCH3), 36.8 (CH2), 28.7 (C(CH3)3), 26.6 (CH2), 18.8 (CHCH3).
7.1.4.1.6. (S)-Methyl 2-[3-(5-amino-2-hydroxyphenyl)propanami-
do]-2-phenyl-2-carboxylate; Boc
pound 16g was synthesized from compound 11g (0.33 g,
1.00 mmol), Boc- -alanine (0.20 g, 1.05 mmol), N-methylmorpho-
L-alanine derivative 16g. Com-
L
line (0.10 g, 1.00 mmol) and IBCF (0.14 g, 1.00 mmol) in dry THF
(20 mL). No further purification was required. Yield: (0.45 g, 89%)
of pale pink crystals, mp 82–84 °C. HRMS (NSI) for C26H33N3O7. Cal-
culated mass of molecular ion 500.2391 [M+H]+. Measured mass:
500.2394; IR mmax cmÀ1 3304, 3300–2800, 1651, 1498, 1366,
1230, 1160, 1022, 697; 1H NMR (400 MHz; d6-DMSO) dH 9.59
(1H, s, NH), 9.16 (1H, s, OH), 8.73 (1H, d, J = 6.9 Hz, NH), 7.42–
7.32 (5H, m, Ar-H), 7.25 (2H, m, Ar-H), 6.98 (1H, d, J = 7.3 Hz,
NH), 6.69 (1H, d, J = 8.7 Hz, Ar-H), 5.42 (1H, d, J = 7.3 Hz, CH),
4.08 (1H, p, J = 7.1 Hz, CH), 3.62 (3H, s, CH3), 2.70 (2H, m, CH2),
2.44 (2H, t, J = 7.6 Hz, CH2), 1.38 (9H, s, 3Â CH3), 1.23 (3H, d,
J = 7.3 Hz, CH3); 13C NMR (68 MHz; d6-DMSO) dC 172.4 (C@O),
171.7 (C@O), 171.5 (C@O), 155.6 (C@O), 151.5 (Ar-C), 136.8 (Ar-
C), 131.2 (Ar-C), 129.2 (2Â Ar-C), 128.7 (Ar-C), 128.3 (2Â Ar-C),
127.8 (Ar-C), 121.9 (Ar-C), 119.0 (Ar-C), 115.2 (Ar-C), 78.5