Molecules 2021, 26, 1716
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6.7 Hz, 1H, CH-CH3), 1.13 (d, J = 6.7 Hz, 3H, CH3). 13C-NMR (100 MHz, DMSO-d6, ppm)
δC 170.4 (C=O), 156.4, 155.2, 145.0, 137.8, 131.3, 130.3, 127.8, 121.4, 120.6, 112.6, 106.5, and
97.2 (14C, Ar-C), 69.2 (CH2), 54.5 (CH), 48.1 (CH2), 15.9 (CH3). HR-ESI MS m/z 325.1546
[M + H]+.
(S)-2-((3-((Quinolin-5-yloxy)methyl)benzyl)amino)propanamide (7a)
Yield: 80%. IR (KBr, cm−1
1558. 1H-NMR (400 MHz, DMSO-d6, ppm) δH 8.91 (dd, J = 4.1, 1.6 Hz, 1H, HAr), 8.58
d, J = 8.4 Hz, 1H, HAr), 7.68 (m, 1H, HAr), 7.62 (d, J = 8.4 Hz, 1H, HAr), 7.51–7.54 (m, 2H,
) ν 3320, 3157, 2659, 2050, 1690 (C=O), 1639 (C=N), 1595,
(
HAr, CONH2), 7.32–7.44 (m, 4H, HAr), 7.18 (d, J = 7.6 Hz, 1H, HAr), 7.04 (s, 1H, CONH2),
5.32 (s, 2H, OCH2), 3.74 (d, J = 13.6 Hz, 1H, Ar-CH2), 3.59 (d, J = 13.6 Hz, 1H, Ar-CH2), 3.04
(q, J = 7.0 Hz, 1H, CH-CH3), 1.14 (d, J = 7.0 Hz, 3H, CH3). 13C-NMR (100 MHz, DMSO-d6
,
ppm) δC 170.4 (C=O), 154.1, 145.5, 140.2, 139.4, 136.4, 135.1, 132.3, 130.1, 129.4, 128.8, 128.1,
121.3, 121.1, 113.3, and 109.0 (15C, Ar-C), 70.2 (CH2), 54.6 (CH), 48.4 (CH2), 16.0 (CH3).
HR-ESI MS 336.1707 [M + H]+.
(S)-2-((4-((Quinolin-5-yloxy)methyl)benzyl)amino)propanamide (7b)
Yield: 66%. IR (KBr, cm−1
1558. 1H-NMR (400 MHz, DMSO-d6, ppm) δH 8.90 (dd, J = 3.9, 1.4 Hz, 1H, HAr), 8.56
d, J = 8.4 Hz, 1H, HAr), 7.67 (m, 1H, HAr), 7.60 (d, J = 8.4 Hz, 1H, HAr), 7.49–7.53 (m, 3H,
) ν 3384, 3156, 2659, 2058, 1689 (C=O), 1639 (C=N), 1595,
(
HAr, CONH2), 7.34–7.39 (m, 3H, HAr), 7.17 (d, J = 7.6 Hz, 1H, HAr), 7.02 (br s, 1H, CONH2),
5.31 (s, 2H, OCH2), 3.70 (d, J = 13.6 Hz, 1H, Ar-CH2), 3.56 (d, J = 13.6 Hz, 1H, Ar-CH2), 3.02
(q, J = 7.0 Hz, 1H, CH-CH3), 1.14 (d, J = 7.0 Hz, 3H, CH3). 13C-NMR (100 MHz, DMSO-d6
,
ppm) δC 170.4 (C=O), 154.0, 145.8, 139.9, 139.4, 136.8, 134.8, 131.8, 130.5, 127.9, 121.3, 121.1,
113.6, and 108.9 (15C, Ar-C), 70.0 (CH2), 54.6 (CH), 48.1 (CH2), 16.0 (CH3). HR-ESI MS m/z
336.1707 [M + H]+.
(S)-2-((3-((Quinolin-6-yloxy)methyl)benzyl)amino)propanamide (7c)
Yield: 85%. IR (KBr, cm−1
)
ν
3290, 3158, 2913, 2660, 2062, 1964, 1696 (C=O), 1617
1
(C=N), 1617, 1600. H-NMR (400 MHz, DMSO-d6, ppm) δH 8.75 (dd, J = 4.2, 1.7 Hz, 1H,
HAr), 8.25 (m, 1H, HAr), 7.94 (dd, J = 9.5, 0.8 Hz, 1H, HAr), 7.47–7.50 (m, 4H, HAr, CONH2),
7.31–7.40 (m, 4H, HAr), 7.02 (br s, 1H, CONH2), 5.23 (s, 2H, OCH2), 3.72 (d, J = 13.6 Hz, 1H,
Ar-CH2), 3.58 (d, J = 13.6 Hz, 1H, Ar-CH2), 3.03 (q, J = 7.0 Hz, 1H, CH-CH3), 1.14 (d, J = 7.0
Hz, 3H, CH3). 13C-NMR (100 MHz, DMSO-d6 ppm) δC 170.4 (C=O), 157.9, 143.7, 142.4,
,
136.3, 134.6, 132.2, 130.3, 130.1, 130.0, 128.9, 128.5, 126.9, 123.1, 122.4, and 107.9 (15C, Ar-C),
69.9 (CH2), 54.6 (CH), 48.3 (CH2), 16.0 (CH3). HR-ESI MS m/z 336.1708 [M + H]+.
(S)-2-((4-((Quinolin-6-yloxy)methyl)benzyl)amino)propanamide (7d)
Yield: 82%. IR (KBr, cm−1
)
ν
3357, 3175, 3076, 2969, 2661, 1689 (C=O), 1616 (C=N),
1
1600, 1493. H-NMR (400 MHz, DMSO-d6, ppm) δH 8.74 (dd, J = 4.2, 1.7 Hz, 1H, HAr), 8.24
(dd, J = 8.4, 1.1 Hz, 1H, HAr), 7.93 (d, J = 8.9 Hz, 1H, HAr), 7.45–7.49 (m, 5H, HAr, CONH2),
7.36–7.38 (m, 3H, HAr), 7.01 (br s, 1H, CONH2), 5.21 (s, 2H, OCH2), 3.70 (d, J = 13.6 Hz, 1H,
Ar-CH2), 3.55 (d, J = 13.6 Hz, 1H, Ar-CH2), 3.01 (q, J = 7.0 Hz, 1H, CH-CH3), 1.13 (d, J = 7.0
Hz, 3H, CH3). 13C-NMR (100 MHz, DMSO-d6 ppm) δC 170.6 (C=O), 158.2, 143.8, 143.2,
,
137.2, 135.1, 131.7, 130.7, 130.5, 128.6, 127.2, 123.8, 122.7, 108.1 (15C, Ar-C), 69.9 (CH2), 54.7
(CH), 48.3 (CH2), 16.1 (CH3). HR-ESI MS m/z 336.1708 [M + H]+.
(S)-2-((3-((Quinolin-7-yloxy)methyl)benzyl)amino)propanamide (7e)
Yield: 81%. IR (KBr, cm−1
) ν 3300, 3137, 2743, 1694 (C=O), 1643 (C=N), 1643, 1609.
1H-NMR (400 MHz, DMSO-d6, ppm) δH 8.81 (dd, J = 4.5, 2.0 Hz, 1H, HAr), 8.28 (dd, J = 8.1,
1.7 Hz, 1H, HAr), 7.90 (d, J = 9.0 Hz, 1H, HAr), 7.48–7.50 (m, 2H, HAr, CONH2), 7.30–7.39
(m, 6H, HAr), 7.02 (br s, 1H, CONH2), 5.27 (s, 2H, OCH2), 3.71 (d, J = 13.6 Hz, 1H, Ar-CH2),
3.57 (d, J = 13.6 Hz, 1H, Ar-CH2), 3.03 (q, J = 7.0 Hz, 1H, CH-CH3), 1.14 (d, J = 7.0 Hz, 3H,
CH3). 13C-NMR (100 MHz, DMSO-d6, ppm) δC 170.4 (C=O), 162.2, 145.0, 144.5, 140.7, 135.8,