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300 MHz): d = 8.46 (1H, d, J = 5.4 Hz, H-2), 8.43 (1H,
d, J = 7.0 Hz, H-5), 7.90 (1H, d, J = 1.7 Hz, H-8),
7.73–7.72 (1H, dd, J = 1.8, 8.8 Hz, H-6), 7.00 (1H, d,
J = 6.4 Hz, H-3), 3.91–3.86 (1H, m, COCHCH3NHCH3),
3.84–3.76 (4H, m, NH(CH2)2NHCO), 2.64 (3H, s,
COCHCH3NHCH3), 1.47 (3H, d, J = 6.9 Hz, COCH
CH3NHCH3); 13C NMR (CD3OD, 50 MHz): d = 171.1
(CO, CONH), 157.9 (C, C-4), 144.0 (C, C-2), 141.1 (CH,
C-9), 140.0 (CH, C-7), 128.8 (C, C-8), 126.4 (C, C-5),
120.3 (C, C-6), 117.0 (C, C-10), 100.0 (CH, C-3), 68.2
(CH, CHCH3), 44.2 (CH2, NHCH2), 38.9 (CH2, CH2
NHCO), 31.9 (CH3, NHCH3), 16.3 (CH3, CHCH3); ESI–
MS (m/z): 307.1 [M ? H]? (100); HRMS (m/z): 307.1324
[C15H19ClN4O ? H]? (calcd 307.1320).
(C, C-5), 120.6 (C, C-6), 117.1 (C, C-10), 100.0 (CH, C-3),
68.3 (CH, NHCH), 44.4 (CH2, NHCH2), 39.0 (CH2, CH2
NHCO), 37.5 (CH, CHCH3), 33.6 (CH3, NHCH3), 26.7
(CH2, CH2CH3), 15.1 (CH, CHCH3), 12.5 (CH2, CH2CH3);
ESI–MS (m/z): 349.2 [M ? H]? (100); HRMS (m/z):
349.1794 [C18H25ClN4O ? H]? (calcd 349.1790).
(S)-N-(2-(7-Chloroquinolin-4-ylamino)ethyl)-4-methyl-2-
(methylamino) pentanamide (32) Gummy residue (The
method for synthesis was the same as reported for com-
pound 31. While the amino acid used was (S)-2-(tert-bu-
toxycarbonyl(methyl)amino)-4-methylpentanoic acid. It
1
was obtained as gummy residue in 82 % yield.); H NMR
(CDCl3, 300 MHz): d = 8.67 (1H, d, J = 9.0 Hz, H-2),
8.32 (1H, d, J = 2.1 Hz, H-5), 7.88 (1H, d, J = 6.6 Hz,
H-8), 7.80–7.78 (1H, dd, J = 2.0, 8.9 Hz, H-6), 6.77 (1H, d,
J = 4.2 Hz, H-3), 3.53–3.37 (5H, m, NH(CH2)2
NHCOCHNHCH3), 2.64 (3H, s, COCHNHCH3), 1.84–1.81
(1H, m, COCHCH2CH(CH3)2), 1.65–1.62 (2H, m,
COCHCH2CH(CH3)2), 0.95 (6H, d, J = 5.7 Hz,
COCHCH2CH(CH3)2); 13C NMR (CDCl3, 50 MHz,):
d = 168.9 (CO, CONH), 156.4 (C, C-4), 142.5 (C, C-2),
140.4 (CH, C-9), 138.7 (CH, C-7), 125.8 (C, C-8), 119.6 (C,
C-5), 116.2 (C, C-6), 111.9 (C, C-10), 98.5 (CH, C-3), 67.3
(CH, NHCH), 60.7 (CH2, NHCH2), 43.1 (CH2, CHCH2),
38.9 (CH2, CH2NHCO), 31.6 (CH3, NHCH3), 24.9 (CH,
CHCH3), 23.1 (CH3, CH3CHCH3), 22.0 (CH3, CH3
CHCH3); ESI–MS (m/z): 349.1 [M ? H]? (100); HRMS
(m/z): 349.1795 [C18H25ClN4O ? H]? (calcd 349.1790).
(S)-N-(2-(7-Chloroquinolin-4-ylamino) ethyl)-3-methyl-2-
(methylamino) butanamide (30) Gummy residue (The
method for synthesis was the same as reported for com-
pound 29. While the amino acid used was (S)-2-(tert-bu-
toxycarbonyl(methyl)amino)-3-methylbutanoic acid. It was
obtained as gummy residue in 85 % yield.); 1H NMR
(CDCl3, 300 MHz): d = 8.47 (1H, d, J = 5.6 Hz, H-2),
8.17 (1H, d, J = 8.9 Hz, H-5), 7.78 (1H, d, J = 2.0 Hz,
H-8), 7.49–7.46 (1H, dd, J = 2.1, 9.0 Hz, H-6), 6.68 (1H,
d, J = 5.5 Hz, H-3), 3.42–3.34 (5H, m, NH(CH2)2
NHCOCHNHCH3), 3.20 (3H, s, COCHNHCH3),
2.09–1.98 (1H, m, COCHCH(CH3)2), 0.91–0.84 (6H, m,
COCHCH(CH3)2); 13C NMR (CDCl3, 50 MHz,):
d = 170.1 (CO, CONH), 159.1 (C, C-4), 145.3 (C, C-2),
142.3 (CH, C-9), 141.2 (CH, C-7), 130.1 (C, C-8), 127.5
(C, C-5), 121.6 (C, C-6), 118.2 (C, C-10), 101.3 (CH, C-3),
69.4 (CH, NHCH), 45.5 (CH2, NHCH2), 39.9 (CH2, CH2-
NHCO), 34.4 (CH3, NHCH3), 32.3 (CH, CH3CHCH3), 20.0
(CH3, CH3CHCH3), 19.5 (CH3, CH3CHCH3); ESI–MS (m/
z): 335.1[M ? H]?(100); HRMS (m/z): 335.1634 [C17
H23ClN4O ? H]? (calcd 335.1633).
(S)-N-(2-(7-Chloroquinolin-4-ylamino)ethyl)-2-(methylamino)-
3-phenylpropa namide (33) Gummy residue (The method
for synthesis was the same as reported for compound 32.
While the amino acid used was (S)-2-(tert-butoxycar-
bonyl(methyl)amino)-3-phenylpropanoic acid. It was
obtained as gummy residue in 91 % yield.); 1H NMR
(CD3OD, 300 MHz): d = 8.45 (1H, d, J = 5.6 Hz, H-2),
8.45 (1H, d, J = 6.5 Hz, H-5), 8.36 (1H, d, J = 9.0 Hz,
H-8), 7.91–7.89 (1H, dd, J = 2.0, 8.9 Hz, H-6), 7.76–7.47
(5H, m, CH2C6H5), 6.90 (1H, d, J = 6.7 Hz, H-3),
4.08–3.87 (1H, m, COCHNHCH3), 3.53 (4H, s,
NH(CH2)2NHCO), 3.22–3.08 (2H, m, COCH2C6H5), 2.66
(3H, s, COCHNHCH3); 13C NMR (CD3OD, 50 MHz):
d = 166.9 (CO, CONH), 153.7 (C, C-4), 150.3 (C, C-2),
149.2 (CH, C-9), 144.4 (1Caromatic), 139.9 (CH, C-7), 139.3
(C, C-8), 138.2, 138.1 (4Caromatic), 135.7 (1Caromatic), 129.7
(C, C-5), 109.5 (C, C-6), 107.8 (C, C-10), 98.3 (CH, C-3),
73.4 (CH, NHCH), 46.9 (CH2, NHCH2), 42.6 (CH2, CH2
NHCO), 41.4 (CH2, CH2Ph), 40.0 (CH3, NHCH3); ESI–
MS (m/z): 383.1 [M ? H]? (100); HRMS (m/z): 383.1640
[C21H23ClN4O ? H]? (calcd 383.1633).
(2S,3S)-N-(2-(7-Chloroquinolin-4-ylamino)ethyl)-3-methyl-
2-(methylamino)pentanamide (31) Gummy residue (The
method for synthesis was the same as reported for com-
pound 30. While the amino acid used was (2S,3S)-2-(tert-
butoxycarbonyl(methyl)amino)-3-methylpentanoic acid. It
1
was obtained as gummy residue in 80 % yield.); H NMR
(CD3OD, 300 MHz): d = 8.47 (1H, d, J = 5.8 Hz, H-2),
8.42 (1H, d, J = 8.8 Hz, H-5), 7.89 (1H, d, J = 1.7 Hz,
H-8), 7.74–7.71 (1H, dd, J = 1.7, 8.9 Hz, H-6), 7.00 (1H,
d, J = 6.9 Hz, H-3), 3.79–3.71 (m, 4H, NH(CH2)2CO),
3.68 (3H, s, COCHNHCH3), 3.57–3.53 (1H, m,
CHCHCH3CH2CH3), 1.50–1.38 (1H, m, CHCHCH3CH2
CH3), 1.22–1.08 (2H, m, CHCHCH3CH2CH3), 0.99–0.95
(3H, m, CHCHCH3CH2CH3), 0.93–0.90 (3H, m,
CHCHCH3CH2CH3); 13C NMR (CD3OD, 50 MHz):
d = 168.9 (CO, CONH), 157.8 (C, C-4), 143.9 (C, C-2),
141.6 (CH, C-9), 140.0 (CH, C-7), 129.4 (C, C-8), 126.6
(S)-N-(2-(7-Chloroquinolin-4-ylamino)ethyl)-1-methylpyrro-
lidine-2-carboxamide (35) White solid (The method for
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