A new and potent class of quinoline derivatives against cancer
(1H, m, H5, H2), 7.84 (1H, d, J = 8.2 Hz, H5), 7.74 (1H, t,
4-(2,6-Dichlorobenzylidenehydrazinyl)quinoline
J = 7.5 Hz, H7), 7.67–7.63 (2H, m, H6, H5
(2H, m, H7, H9), 7.41 (1H, d, J = 6.0 Hz, H3), 7.27–7.23
(1H, m, H
8) ppm; 13C NMR (100 MHz, DMSO-d6):
´
), 7.57–7.48
hydrochloride (5f, C16H12Cl3N3)
1
´
´
Yield: 89 %; yellow solid; m.p.: 227–229 °C; H NMR
(400 MHz, DMSO-d6): d = 11.46 (1H, s, NH), 8.70 (1H,
´
d = 155.5, 146.2, 145.5, 143.2, 135.9, 130.6, 129.5,
128.9, 127.8, 125.8, 124.9, 123.2, 117.2, 100.3 ppm; IR
s, H
(1H, d, J = 8.0 Hz, H8), 7.70 (1H, t, J = 8.0 Hz, H7),
7.60–7.58 (2H, m, H6, H8), 7.52 (1H, t, J = 8.0 Hz, H6),
7.40 (1H, t, J = 8.0 Hz, H9), 7.27 (1H, d, J = 5.2 Hz, H3)
´
3), 8.43 (1H, s, H2), 8.38 (1H, d, J = 8.0 Hz, H5), 7.83
(KBr): vꢀ = 3189 (N–H), 2908 (N?–H), 1615 (C=N) cm-1
HRMS (ESI): m/z = 264.1015 ([M?H]?).
;
´
´
´
ppm; 13C NMR (100 MHz, DMSO-d6): d = 153.2, 152.3,
150.4, 144.5, 137.3, 132.8, 126.8, 123.5, 117.7, 115.1,
113.7, 110.2, 99.8 ppm; IR (KBr): vꢀ = 3485 (N–H), 1579
(C=N) cm-1; HRMS (ESI): m/z = 314.0332 ([M?H]?).
4-(3-Chlorobenzylidenehydrazinyl)quinoline hydrochloride
(5c, C16H13Cl2N3)
1
Yield: 80 %; yellow solid; m.p.: 223–225 °C; H NMR
(400 MHz, DMSO-d6): d = 8.63 (1H, s, H3), 8.60 (1H, d,
´
4-(3,4-Dimethoxybenzylidenehydrazinyl)quinoline
J = 8.4 Hz, H5), 8.52 (1H, d, J = 6.0 Hz, H2), 7.94–7.92
hydrochloride (5g, C18H18ClN3O2)
´
(2H, m, H5, H8), 7.86–7.78 (2H, m, H6, H7), 7.64 (1H, t,
1
Yield: 82 %; yellow solid; m.p.: 240–241 °C; H NMR
J = 7.5 Hz, H
8´), 7.56–7.46 (3H, m, H3, H7
´
, H9
) ppm; 13C
´
(400 MHz, DMSO-d6): d = 14.70 (1H, s, NH), 12.88 (1H,
s, NH), 9.16 (1H, s, H3´), 8.84 (1H, d, J = 7.2 Hz, H5), 8.68
NMR (100 MHz, DMSO-d6): d = 150.4, 145.7, 145.3,
142.7, 136.7, 133.8, 131.5, 130.6, 129.7, 126.3, 125.9,
125.6, 123.8, 123.1, 116.7, 100.6 ppm; IR (KBr): vꢀ = 3163
(N–H), 2908 (N?–H), 1608 (C=N) cm-1; HRMS (ESI): m/
z = 282.0717 ([M?H]?).
(1H, d, J = 6.8 Hz, H2), 8.10 (1H, d, J = 8.4 Hz, H8), 8.03
(1H, dd, J = 8.4, 7.6 Hz, H7), 7.81 (1H, dd, J = 7.6,
´
7.2 Hz, H6), 7.55 (2H, m, H3, H5), 7.19 (1H, d, J = 8.3 Hz,
H
´
8, H9
), 3.87 (6H, s, OCH3) ppm; 13C NMR (100 MHz,
´
DMSO-d6): d = 152.7, 152.4, 148.5, 146.4, 142.2, 138.2,
133.6, 127.0, 126.7, 124.5, 123.9, 120.0, 117.1, 115.0,
99.8, 61.4, 55.8 ppm; IR (KBr): vꢀ = 2766 (N?–H), 1612
(C=N) cm-1; HRMS (ESI): m/z = 308.1321 ([M?H]?).
4-(3-Bromobenzylidenehydrazinyl)quinoline hydrochloride
(5d, C16H13BrClN3)
Yield: 65 %; yellow solid; m.p.: 304 °C; 1H NMR
(400 MHz, DMSO-d6): d = 14.77 (1H, s, NH), 13.10
(1H, s, NH), 8.91–8.89 (2H, m, H
J = 6.9 Hz, H2), 8.11–8.09 (1H, m, H8, H5), 8.03 (1H, t,
J = 7.7 Hz, H7), 7.87 (1H, d, J = 7.8 Hz, H7), 7.81 (1H, t,
J = 7.7 Hz, H6), 7.73 (2H, d, J = 8.4 Hz, H5, H9), 7.70–
7.73 (2H, m, H3, H8), 7.49 (1H, d, J = 7.8 Hz, H9) ppm;
´
3, H5), 8.69 (1H, d,
4-(2,5-Dimethoxybenzylidenehydrazinyl)quinoline
´
hydrochloride (5h, C18H18ClN3O2)
1
´
Yield: 85 %; yellow solid; m.p.: 284–286 °C; H NMR
´
´
(400 MHz, DMSO-d6): d = 14.61 (1H, s, NH), 12.75 (1H,
s, NH), 9.13 (1H, s, H3´), 8.78 (1H, d, J = 8.3 Hz, H5), 8.65
´
´
13C NMR (100 MHz, DMSO-d6): d = 152.6, 148.6, 172.5,
138.2, 135.9, 135.6, 133.8, 133.4, 131.1, 129.4, 126.9,
123.9, 122.4, 120.1, 115.1, 100.2 ppm; IR (KBr): vꢀ = 3152
(N–H), 2684 (N?–H), 1612 (C=N) cm-1; HRMS (ESI): m/
z = 326.0217 ([M?H]?).
(1H, d, J = 6.8 Hz, H2), 8.08 (1H, d, J = 8.3 Hz, H8), 8.02
(1H, dd, J = 8.3, 7.2 Hz, H7), 7.80 (1H, dd, J = 8.3,
7.2 Hz, H6), 7.68 (1H, d, J = 6.8 Hz, H3), 7,56 (1H, s, H9´
),
7.14-7.09 (2H, m, H6, H7), 3.87 (3H, s, OCH3), 3.81 (3H, s,
´
´
OCH3) ppm; 13C NMR (100 MHz, DMSO-d6): d = 153.4,
152.9, 152.3, 145.9, 142.6, 138.3, 133.9, 127.1, 123.5,
122.3, 120.3, 118.7, 115.1, 113.7, 109.8, 100.1, 56.4,
4-(3-Methoxybenzylidenehydrazinyl)quinoline hydrochlo-
55.7 ppm; IR (KBr): vꢀ = 2771 (N?–H), 1589 (C=N) cm-1
HRMS (ESI): m/z = 308.1319 ([M?H]?).
;
ride (5e, C17H16ClN3O)
1
Yield: 77 %; yellow solid; m.p.: 261–262 °C; H NMR
(400 MHz, DMSO-d6): d = 14.76 (1H, s, NH), 13.12 (1H,
s, NH), 9.01-8.99 (2H, m, H3´, H5), 8.63 (1H, d,
4-(3,4,5-Trimethoxybenzylidenehydrazinyl)quinoline
hydrochloride (5i, C19H20ClN3O3)
Yield: 68 %; E/Z ratio = 67:33; yellow solid; m.p.: 288–
J = 7.0 Hz, H2), 8.10 (1H, d, J = 8.0 Hz, H8), 7.98 (1H,
t, J = 8.0 Hz, H7), 7.75 (1H, t, J = 8.0 Hz, H6), 7.61 (1H,
1
289 °C; H NMR (400 MHz, DMSO-d6): d = 14.52 (1H,
s, NH), 12.97 (1H, s, NH), 8.83 (1H, s, H3´), 8.89 (1H, d,
d, J = 7.0 Hz, H3), 7.42-7.37 (3H, m, H5
´
H8´
, H9´
), 7.06
7), 3.85 (3H, s, OCH3) ppm; 13C
(1H, d, J = 7.5 Hz, H
´
J = 8.4 Hz, H5), 8.67–8.65 [1.6H, d, J = 6.8 Hz, H2, H3´
NMR (100 MHz, DMSO-d6): d = 159.6, 152.5, 150.3,
142.3, 138.2, 134.9, 133.7, 130.1, 126.8, 124.4, 120.4,
120.0, 116.9, 115.1, 111.8, 99.9, 55.3 ppm; IR (KBr):
vꢀ = 3414 (N–H), 2688 (N?–H), 1589 (C=N) cm-1; HRMS
(ESI): m/z = 278.1213 ([M?H]?).
(Z)], 8.05 (1H, d, J = 8.4 Hz, H8), 8.03 (1H, t, J = 8.4 Hz,
H7), 7.80 (1H, t, J = 8.4 Hz, H6), 7.69 (1H, d, J = 6.8 Hz,
H3), 7.22 [1H, s, H5
´
, H
´
9(Z)], 7.19 (2H, s, H5
´
, H9´), 3.90 (6H,
s, OCH3), 3.84 (6H, s, OCH3), 3.75–3.73 [4.7H, m, OCH3
123