1364
D. Zhao et al. / Bioorg. Med. Chem. 23 (2015) 1356–1365
(ArC), 149.45 (ArC), 154.77 (ArC),162.67 (C, C@O), 172.16 (C, C@O).
ESI-MS m/z: 319.7[MÀH]À.
7.12.15. 3-[(5-tertButyl-2-methyl-1-propyl-1H-pyrrole-3-
carbonyl)amino]-3-(2-nitrophenyl) propionic acid (29)
Light white solid; yield: 55.6%; mp 179.2–180.0 °C. 1H NMR
(DMSO-d6, 300 MHz): d 0.89–0.94 (t, 3H), 1.32 (s, 9H), 1.49–1.57
(q, 2H), 2.33 (s, 3H), 2.66–2.96 (m, 2H), 3.78–3.84 (t, 2H), 5.65–
5.70 (q, 1H), 6.34 (s, 1H), 7.44–7.49 (t, 1H), 7.67–7.76 (m, 2H),
7.87–7.90 (m, 1H), 8.12 (d, 1H, J = 7.38 Hz), 12.34 (s, 1H). 13C
NMR (DMSO): 11.18 (CH3), 11.39 (CH3), 24.36 (CH2), 31.11
(3 Â CH3), 32.08 (C), 40.60 (CH2), 45.67 (CH), 46.53 (CH2), 103.87
(ArCH), 112.83 (ArC), 124.25 (ArCH), 128.46 (ArCH), 128.94 (ArCH),
133.99 (ArC), 134.25 (ArC), 139.24 (ArCH), 139.51 (ArC), 148.60
(ArC), 165.05 (C, C@O), 172.01 (C, C@O). ESI-MS m/z: 413.9
[MÀH]À.
7.12.10. 3-[(2,5-Dimethylfuran-3-carbonyl)amino]-3-(4-
isopropylphenyl) propionic acid (24)
Light white solid; yield: 58.6%; mp: 149.3–150.2 °C. 1H NMR
(DMSO, 300 MHz): d 1.17 (d, 6H, J = 8.4 Hz), 2.21 (s, 3H), 2.40 (s,
3H), 2.68–2.86 (m, 2H), 5.29–5.36 (q,1H), 6.49 (s, 1H), 7.17 (d,
2H, J = 8.13 Hz), 7.26 (d, 2H, J = 8.13 Hz), 8.19 (d, 1H, J = 8.4 Hz),
12.21 (s, 1H); 13C NMR (DMSO): 13.44 (CH3), 13.53 (CH3), 24.36
(2 Â CH3), 33.55 (CH), 41.07 (CH2), 49.42 (CH), 105.48 (ArCH),
116.64 (ArC), 126.59 (2 Â ArCH), 126.98 (2 Â ArCH), 140.83 (ArC),
147.40 (ArC), 149.36 (ArC), 154.64 (ArC), 162.55 (C, C@O), 172.39
(C, C@O). ESI-MS m/z: 327.7 [MÀH]À.
7.12.16. 3-[(5-tertButyl-2-methyl-1-propyl-1H-pyrrole-3-
carbonyl)amino]-3-(4-methoxyphenyl)propionic acid (30)
Light white solid; yield: 54.5%; mp: 205.4–206.2 °C. 1H NMR
(DMSO-d6, 300 MHz): d 0.90–0.95 (t, 3H), 1.30 (s, 9H), 2.40 (s,
3H), 2.64–2.80 (m, 2H), 3.71 (s, 3H), 3.79–3.85 (t, 2H), 5.28–5.35
(q, 1H), 6.27 (s, 1H), 6.85 (d, 2H, J = 8.55 Hz), 7.26 (d, 2H,
J = 8.61 Hz), 7.79 (d, 1H, J = 8.55 Hz), 12.13 (s, 1H). 13C NMR
(DMSO): 11.21 (CH3), 11.41 (CH3), 24.39 (CH2), 31.13 (3 Â CH3),
32.07 (C), 41.29 (CH2), 46.52 (CH2), 48.74 (CH), 55.48 (CH3),
103.87 (ArCH), 113.41 (ArC), 113.93 (2 Â ArCH), 128.22 (2 Â ArCH),
133.86 (ArC), 136.07 (ArC), 139.08 (ArC), 158.49 (ArC), 164.68 (C,
C@O),, 172.63 (C, C@O). ESI-MS m/z: 399.0 [MÀH]À.
7.12.11. 3-[(2,5-Dimethylfuran-3-carbonyl)amino]-3-m-tolyl
propionic acid (25)
Light white solid; yield: 57.3%; mp: 132.1–132.9 °C. 1H NMR
(DMSO, 300 MHz): d 2.21 (s, 3H), 2.28 (s, 3H), 2.40 (s, 3H), 2.65–
2.84 (m, 2H), 5.30–5.32 (q, 1H), 6.50 (s, 1H), 7.02–7.19 (m, 4H),
8.19 (d, 1H, J = 8.34 Hz), 12.21 (s, 1H); 13C NMR (DMSO): 13.44
(CH3), 13.53 (CH3), 21.58 (CH3), 41.17 (CH2), 49.68 (CH), 105.49
(ArCH), 116.64 (ArCH), 124.09 (ArC), 127.64 (ArCH), 127.99 (ArCH),
128.63 (ArCH), 137.70 (ArC), 143.41 (ArC), 149.38 (ArC), 154.64
(ArC), 162.55 (C, C@O), 172.34 (C, C@O). ESI-MS m/z: 299.8[MÀH]À.
7.12.12. 3-(2-Bromophenyl)-3-[(2,5-dimethylfuran-3-
carbonyl)amino] propionic acid (26)
Light white solid; yield: 57.8%; mp: 188.7–190.0 °C. 1H NMR
7.12.17. 3-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-
carbonyl)amino]-3-(3,4-dichloro-phenyl) propionic acid (31)
Light white solid; yield: 52.7%; mp: 187.7–189.3 °C. 1H NMR
(DMSO-d6, 300 MHz): d 2.30 (s, 3H), 2.80–2.82 (m, 2H), 5.30–5.37
(q, 1H), 7.40–7.43 (q, 1H), 7.50–7.68 (m, 7H), 8.61 (d, 1H,
J = 8.07 Hz), 12.48 (s, 1H); 13C NMR (DMSO): 13.70 (CH3), 40.68
(CH2), 49.58 (CH), 115.40 (ArC), 125.77 (2 Â ArCH), 126.63
(ArCH),127.59 (ArCH), 129.17 (ArCH), 129.36 (ArCH), 129.81
(2 Â ArCH), 130.08 (ArC), 131.03 (ArC), 131.39 (ArC), 137.70
(ArC), 144.06 (ArC),149.08 (ArC), 161.20 (C, C@O),172.02 (C,
C@O). ESI-MS m/z: 449.9 [MÀH]À.
(DMSO, 300 MHz):
d 2.23 (s, 3H), 2.39 (s,3H), 2.65–2.84
(m,2H),5.60–5.65 (q,1H), 6.56 (s,1H), 7.15–7.21 (m,1H), 7.33–7.38
(t, 1H), 7.47 (d, 1H, J = 7.68 Hz), 7.58 (d, 1H, J = 7.83 Hz), 8.37 (d,
1H, J = 7.77 Hz); 13C NMR (DMSO): 13.44 (CH3), 13.51 (CH3),
40.62 (CH2), 49.82 (CH), 105.51 (ArCH), 116.63 (ArC), 122.58
(ArC), 128.09 (ArCH), 128.40 (ArCH), 129.39 (ArCH), 133.05 (ArCH),
142.51 (ArC), 149.46 (ArC), 154.86 (ArC), 162.77 (C, C@O), 171.94
(C, C@O). ESI-MS m/z: 363.7 [MÀH]À.
7.12.13. 3-(2-Bromophenyl)-3-[(5-tertbutyl-2-methyl-1-propyl-
1H-pyrrole-3-carbonyl)amino] propionic acid (27)
Light white solid; yield: 51.4%; mp: 171.4–172.1 °C. 1H NMR
(DMSO-d6, 300 MHz): d 0.90–0.95 (t, 3H), 1.33 (s, 9H), 1.54–1.57
(q, 2H), 2.38 (s, 3H), 2.54–2.77 (m, 2H), 3.80–3.86 (t, 2H), 5.59–
5.65 (q, 1H), 6.38 (s, 1H), 7.14–7.18 (t, 1H), 7.32–7.37 (t, 1H),
7.48 (d, 1H, J = 7.68 Hz), 7.56 (d, 1H, J = 7.38 Hz), 8.03 (d, 1H,
J = 7.74 Hz); 13C NMR (DMSO):11.21 (CH3), 11.42 (CH3), 24.41
(CH2), 31.15 (3 Â CH3), 32.09 (C), 40.59 (CH2), 46.55 (CH), 49.63
(CH2), 103.97 (ArCH), 113.17 (ArC), 122.58 (ArC), 128.23 (ArC),
128.26 (ArCH), 129.14 (ArCH), 132.91 (ArCH), 134.11 (ArC),
139.17 (ArCH), 143.27 (ArC), 164.88 (C, C@O), 172.25 (C, C@O).
ESI-MS m/z: 447.1 [MÀH]À.
7.12.18. 3-(2-Bromophenyl)-3-[(5-chloro-3-methyl-1-phenyl-
1H-pyrazole-4-carbonyl)amino] propionic acid (32)
Light white solid; yield: 55.8%; mp: 196.0–197.0 °C. 1H NMR
(DMSO-d6, 300 MHz): d 2.30 (s, 3H), 2.68 (d, 2H, J = 7.56 Hz),
5.64–5.66 (q, 1H), 7.19–7.24 (t, 1H), 7.37–7.42 (t, 1H), 7.57–7.63
(m, 7H), 8.68 (s, 1H), 12.46 (s, 1H). 13C NMR (DMSO): 13.69
(CH3), 40.56 (CH2), 50.31 (CH), 115.59 (ArC), 122.62 (ArC), 125.74
(2 Â ArCH), 126.55 (ArCH), 128.18 (ArCH), 128.48 (ArCH), 129.34
(ArCH), 129.59 (ArCH), 129.81 (2 Â ArCH), 133.16 (ArC), 137.72
(ArC), 141.79 (ArC), 149.07 (ArC), 161.17 (C, C@O), 171.98 (C,
C@O). ESI-MS m/z: 461.9 [MÀH]À.
7.12.14. 3-[(5-tertButyl-2-methyl-1-propyl-1H-pyrrole-3-
carbonyl)amino]-3-(4-tertbutyl phenyl) propionic acid (28)
Light white solid; yield: 61.9%; mp: 171.4–172.5 °C. 1H NMR
(DMSO-d6, 300 MHz): d 0.90–0.95 (t, 3H), 1.25 (s, 9H), 1.30 (s,
9H), 1.53–1.56 (q, 2H), 2.40 (s, 3H), 2.66–2.84 (m, 2H), 3.79–3.85
(t, 2H), 5.30–5.38 (q, 1H), 6.29 (s, 1H), 7.25–7.32 (m, 4H), 7.84 (d,
1H, J = 8.52 Hz), 12.16 (s, 1H); 13C NMR (DMSO):11.22 (CH3),
11.41 (CH3), 24.38 (2 Â CH3), 24.41 (CH2), 31.13 (3 Â CH3), 32.07
(C), 33.56 (CH), 41.14 (CH2), 46.52 (CH), 49.06 (CH2), 103.90
(ArCH), 113.37 (ArC), 126.45 (2 Â ArCH),127.05 (2 Â ArCH),
133.90 (ArC), 141.50 (ArC), 147.14 (ArC), 164.71 (C, C@O), 172.65
(C, C@O). ESI-MS m/z: 425.1 [MÀH]À.
7.12.19. 3-(4-tertButylphenyl)-3-[(5-chloro-3-methyl-1-phenyl-
1H-pyrazole-4-carbonyl)amino] propionic acid (33)
Light white solid; yield: 53.9%; mp: 152.4–153.3 °C. 1H NMR
(DMSO-d6, 300 MHz): d 1.27 (s, 9H), 2.31 (s, 3H), 2.72–2.79 (m,
2H), 5.33–5.40 (q, 1H), 7.31–7.38 (m, 4H), 7.48–7.60 (m, 5H),
8.49 (d, 1H, J = 8.31 Hz), 12.35 (s, 1H); 13C NMR (DMSO): 13.76
(CH3), 31.62 (3 Â CH3), 34.64 (C), 41.27 (CH2), 49.89 (CH), 115.74
(ArC), 125.54 (2 Â ArCH), 125.73 (2 Â ArCH), 126.45 (ArCH),
126.64 (2 Â ArCH), 129.29 (ArC), 129.79 (2 Â ArCH), 137.76 (ArC),
139.75 (ArC), 149.05 (ArC),149.74 (ArC), 160.99 (C, C@O), 172.42
(C, C@O). ESI-MS m/z: 438.1 [MÀH]À.