1044 Letters in Drug Design & Discovery, 2019, Vol. 16, No. 9
Liu et al.
CONH-), 8.02 (d, J = 2.7 Hz, 1H, Ar-H), 7.98 (s, 1H, Ar-H),
7.97 – 7.93 (m, 2H, Ar-H), 7.73 (d, J = 8.7 Hz, 2H, Ar-H),
7.53 (d, J = 8.7 Hz, 2H, Ar-H), 7.18 (d, J = 9.0 Hz, 1H, Ar-
H), 7.06 (d, J = 8.8 Hz, 2H, Ar-H), 3.89 (s, 3H,-OCH3), 3.84
(s, 3H, -OCH3); 13C NMR (101 MHz, DMSO) δ 164.60
(C=O), 164.29 (C=O), 161.87, 152.50, 138.33, 132.50,
131.52, 129.49, 126.72, 124.23, 124.14, 121.92, 121.65,
115.14, 113.59, 112.23, 56.16 (-OCH3), 55.41 (-OCH3).
124.68, 123.30, 121.35, 120.41, 119.81, 112.29, 111.94, 56.17
(-OCH3), 55.86 (-OCH3), 32.87 (-CH-), 23.92(2×-CH3).
2.2.19. N- (m-tolyl)-2-Methoxy-5-(2-methoxybenz ami-
do)Benzamide (1n)
Yield: 67%; m.p: 178.6-180.0°C; MS (m/z): 391.1657
[MꢁH]+; IR (KBr, σ/cm-1): 3334.32 (υNH), 1660.09 (υC=O),
1607.75, 1550.53, 1492.69, 1312.74, 1235.16 (υC-N),
1
1179.57, 1020.94, 774.44; H NMR (400 MHz, DMSO) δ
2.2.16. N- (p-tolyl)-2-Methoxy-5-(2-methoxyben zamido)
Benzamide (1k)
10.13 (s, 1H, -CONH-), 10.09 (s, 1H, -CONH-), 8.00 (d, J =
2.7 Hz, 1H, Ar-H), 7.88 (dd, J = 8.9, 2.8 Hz, 1H, Ar-H), 7.63
(dd, J = 7.6, 1.8 Hz, 1H, Ar-H), 7.58 (s, 1H, Ar-H), 7.56 –
7.47 (m, 2H, Ar-H), 7.22 (t, J = 7.8 Hz, 1H, Ar-H), 7.17 (dd,
J = 8.7, 3.7 Hz, 2H, Ar-H), 7.06 (t, J = 7.5 Hz, 1H, Ar-H),
6.91 (d, J = 7.5 Hz, 1H, Ar-H), 3.90 (s, 6H, 2×-OCH3), 2.31
(s, 3H, -CH3); 13C NMR (101 MHz, DMSO) δ 164.15(C=O),
163.86 (C=O), 156.46, 152.52, 138.81, 137.83, 132.23,
131.92, 129.65, 128.45, 124.72, 124.58, 124.18, 123.38,
121.38, 120.40, 120.20, 116.90, 112.31, 111.94, 56.18 (-
OCH3), 55.85 (-OCH3), 21.11 (-CH3).
Yield: 63 %; m.p: 172.8-174.3°C; MS (m/z): 391.1666
[MꢁH]+; IR (KBr, σ/cm-1): 3349.80 (υNH), 1661.16 (υC=O),
1600.86, 1541.18, 1489.32, 1312.62, 1229.88 (υC-N),
1
1177.13, 1016.58, 747.54; H NMR (400 MHz, DMSO) δ
10.14 (s, 1H, -CONH-), 10.10 (s, 1H, -CONH-), 8.00 (s, 1H,
Ar-H), 7.88 (dd, J = 8.9, 2.7 Hz, 1H, Ar-H), 7.63 (d, J = 7.9
Hz, 3H, Ar-H), 7.50 (t, J = 7.8 Hz, 1H, Ar-H), 7.19 – 7.13
(m, 4H, Ar-H), 7.06 (t, J = 7.4 Hz, 1H, Ar-H), 3.89 (s, 6H,
2×-OCH3), 2.28 (s, 3H, -CH3); 13C NMR (101 MHz, DMSO)
δ 164.34 (C=O), 163.94 (C=O), 156.49, 152.50, 136.57,
132.53, 132.32, 132.03, 129.70, 129.15, 124.92, 124.80,
123.27, 121.31, 120.49, 119.71, 112.27, 111.96, 56.22 (-
OCH3), 55.94 (-OCH3), 20.58 (-CH3).
2.2.20. N- (3-ethylphenyl)-2-Methoxy-5- (2-methoxybenz
amido)Benzamide (1o)
Yield: 59%; m.p: 160.2-161.5°C; MS (m/z): 405.1830
[MꢁH]+; IR (KBr, σ/cm-1): 3344.62 (υNH), 1664.15 (υC=O),
1594.57, 1551.09, 1494.95, 1281.27, 1235.48 (υC-N),
1177.47, 1015.05, 749.21, 640.54; 1H NMR (400 MHz,
DMSO) δ 10.13 (s, 1H, -CONH-), 10.11 (s, 1H, -CONH-),
8.00 (d, J = 2.7 Hz, 1H, Ar-H), 7.88 (dd, J = 9.0, 2.7 Hz, 1H,
Ar-H), 7.63 (dd, J = 7.5, 1.8 Hz, 1H, Ar-H), 7.61 (s, 1H, Ar-
H), 7.56 (d, J = 8.1 Hz, 1H, Ar-H), 7.53 – 7.47 (m, 1H, Ar-
H), 7.24 (t, J = 7.8 Hz, 1H, Ar-H), 7.18 (d, J = 3.6 Hz, 1H,
Ar-H), 7.16 (d, J = 4.3 Hz, 1H, Ar-H), 7.06 (t, J = 7.5 Hz,
1H, Ar-H), 6.95 (d, J = 7.5 Hz, 1H, Ar-H), 3.90 (s, 6H, 2×-
OCH3), 2.60 (q, J = 7.6 Hz, 2H, -CH2-), 1.19 (t, J = 7.6 Hz,
3H, -CH2CH3); 13C NMR (101 MHz, DMSO) δ 164.19
(C=O), 163.95 (C=O), 156.47, 152.51, 144.28, 138.93,
132.24, 131.95, 129.66, 128.55, 124.77, 124.68, 123.33,
123.01, 121.34, 120.42, 119.08, 117.17, 112.29, 111.95,
56.18 (-OCH3), 55.86 (-OCH3), 28.25 (-CH2-), 15.52 (-CH3).
2.2.17. N- (4-ethylphenyl)-2-Methoxy-5-(2-methoxybenza
mido)Benzamide (1l)
Yield: 64 %; m.p: 174.0-175.3°C; MS (m/z): 405.1812
[MꢁH]+; IR (KBr, σ/cm-1): 3345.14 (υNH), 1660.02(υC=O),
1601.13, 1545.80, 1491.34, 1316.34, 1288.40, 1232.99 (υC-
N), 1178.99, 1017.94, 752.28; 1H NMR (400 MHz, CDCl3) δ
9.93 (s, 1H, -CONH-), 9.88 (s, 1H, -CONH-), 8.54 (dd, J =
8.8, 2.8 Hz, 1H, Ar-H), 8.31 (d, J = 7.6 Hz, 1H, Ar-H), 7.99
(d, J = 2.8 Hz, 1H, Ar-H), 7.60 (d, J = 8.1 Hz, 2H, Ar-H),
7.52 (t, J = 7.7 Hz, 1H, Ar-H), 7.22 (d, J = 8.0 Hz, 2H, Ar-
H), 7.15 (t, J = 7.6 Hz, 1H, Ar-H), 7.07 (t, J = 8.2 Hz, 2H,
Ar-H), 4.09 (s, 3H, -OCH3), 4.08 (s, 3H, -OCH3), 2.66 (q, J
= 7.6 Hz, 2H, -CH2-), 1.25 (t, J = 7.6 Hz, 3H, -CH2CH3); 13
C
NMR (101 MHz, CDCl3) δ 163.45 (C=O), 162.81 (C=O),
157.47, 153.73, 140.52, 136.05, 133.45, 132.90, 132.63,
128.46, 125.88, 123.90, 122.05, 121.74, 121.65, 120.71,
112.59, 111.66, 56.78 (-OCH3), 56.42 (-OCH3), 28.51 (-
CH2-), 15.83 (-CH3).
2.2.21. N- (3-isopropylphenyl)-2-Methoxy-5-(2-methoxyben
zamido)Benzamide (1p)
Yield: 55 %; m.p: 160.4-161.3°C; MS (m/z): 419.1977
[MꢁH]+; IR (KBr, σ/cm-1): 3351.36 (υNH), 1663.76 (υC=O),
1594.12, 1548.84, 1497.18, 1439.28, 1276.46, 1235.45 (υC-
2.2.18. N- (4-isopropylphenyl)-2-Methoxy-5- (2-metho
xybenzamido)Benzamide (1m)
1
N), 1179.35, 1014.93, 753.59, 650.37; H NMR (400 MHz,
Yield: 62 %; m.p: 184.5-185.7°C; MS (m/z): 419.1964
[MꢁH]+; IR (KBr, σ/cm-1): 3342.61 (υNH), 1660.30 (υC=O),
1600.27, 1546.39, 1490.59, 1316.37, 1289.40, 1232.71 (υC-
N), 1178.14, 1017.63, 753.60; 1H NMR (400 MHz, DMSO) δ
10.14 (s, 1H, -CONH-), 10.10 (s, 1H, -CONH-), 7.99 (d, J =
2.7 Hz, 1H, Ar-H), 7.88 (dd, J = 9.0, 2.7 Hz, 1H, Ar-H), 7.63
(t, J = 7.1 Hz, 3H, Ar-H), 7.50 (t, J = 7.9 Hz, 1H, Ar-H),
7.21 (d, J = 8.3 Hz, 2H, Ar-H), 7.17 (dd, J = 8.7, 5.4 Hz, 2H,
Ar-H), 7.06 (t, J = 7.5 Hz, 1H, Ar-H), 3.89 (s, 3H, -OCH3),
3.89 (s, 3H, -OCH3), 2.86 (sept, J = 6.9 Hz, 1H, -CH-), 1.19
(d, J = 6.8 Hz, 6H, -CH(CH3)2); 13C NMR (101 MHz,
DMSO) δ 164.20(C=O), 163.79(C=O), 156.46, 152.50,
143.64, 136.70, 132.24, 131.94, 129.65, 126.35, 124.79,
DMSO) δ 10.12 (s, 1H, -CONH-), 10.11 (s, 1H, -CONH-),
7.99 (d, J = 2.7 Hz, 1H, Ar-H), 7.88 (dd, J = 8.9, 2.7 Hz, 1H,
Ar-H), 7.66 – 7.62 (m, 2H, Ar-H), 7.56 (dd, J = 7.8, 2.1 Hz,
1H, Ar-H), 7.53 – 7.47 (m, 1H, Ar-H), 7.25 (t, J = 7.9 Hz,
1H, Ar-H), 7.18 (d, J = 4.1 Hz, 1H, Ar-H), 7.16 (d, J = 4.8
Hz, 1H, Ar-H), 7.06 (t, J = 7.5 Hz, 1H, Ar-H), 6.98 (d, J =
7.6 Hz, 1H, Ar-H), 3.90 (s, 6H, 2×-OCH3), 2.88 (sept, J =
6.9 Hz, 1H, -CH-), 1.21 (d, J = 6.9 Hz, 6H, -CH(CH3)2); 13
C
NMR (101 MHz, DMSO) δ 164.19 (C=O), 163.99 (C=O),
156.46, 152.49, 148.97, 138.93, 132.23, 131.96, 129.66,
128.54, 124.78, 123.28, 121.54, 121.30, 120.43, 117.70,
117.32, 112.28, 111.95, 56.17 (-OCH3), 55.87 (-OCH3),
33.48 (-CH-), 23.82 (2×-CH3).