3808
K.D. Thomas et al. / European Journal of Medicinal Chemistry 45 (2010) 3803e3810
4.6.6. 6-Methoxy-2-methyl-4-(4-((piperidin-1-yl)methyl)-1H-
4.6.11. 4-(4-((4-Cyclohexylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-
1,2,3-triazol-1-yl) quinoline (5f)
1-yl)-6-methoxy-2-methylquinoline (5k)
Appearance e off white solid; IR(KBr,cmꢁ1
)
nmax: 2925 (CeH),
Appearance e
white solid; 1H NMR (CDCl3-300 MHz)
1498 (CeH), 1210 (CeO), 1140 (CeN); 1H NMR (CDCl3-300 MHz)
d
ppm ¼ 1.27e1.37 (m, 6H, CH2), 1.67 (m, 2H, CH2), 1.83e2.03 (m,
d
ppm ¼ 1.27e1.30 (m, 2H, CH2), 1.4e1.52 (m, 4H, CH2), 3.1 (m, 4H,
2H, CH2), 2.55e2.58 (m, 1H, NCH2), 2.69e2.71 (m, 4H, NCH2), 2.69
(m, 4H, NCH2), 2.79 (s, 1H, CH3), 3.86 (s, 3H, OCH3), 3.95 (s, 2H,
CH2), 7.22 (d, 1H, J ¼ 2.7 Hz, ArH), 7.37 (s, 1H, ArH), 7.43 (dd, 1H,
J ¼ 9.3 Hz, ArH), 7.97 (s, 1H, ArH), 8.03 (d, 1H, J ¼ 9.3 Hz, ArH); 13C
NCH2), 2.80 (s, 3H, CH3), 3.83 (s, 2H, CH2), 3.86 (s,1H, OCH3), 7.20 (d,
1H, J ¼ 2.7 Hz, ArH), 7.38 (s, 1H, ArH), 7.44 (dd, 1H, J ¼ 9.3 Hz, ArH),
7.99 (s, 1H, ArH), 8.03 (d, 1H, J ¼ 9.3 Hz, ArH); 13C
d
ppm ¼ 22.76,
23.48, 26.18, 49.06, 55.98, 56.61, 107.18, 112.10, 117.02, 118.34,
121.30, 129.75, 134.27, 141.07, 141.10, 156.12, 162.73; LC/MS (ESI-MS)
m/z ¼ 338.19 (M þ 1).
d
ppm (CDCl3-75 MHz) ¼ 23.48, 25.95, 26.40, 28.89, 48.98, 52.03,
56.06, 56.60, 63.90, 107.18, 112.10, 117.02, 118.34, 121.30, 129.75,
134.27, 141.07, 141.10, 156.12, 162.73 LC/MS (ESI-MS) m/z ¼ 421.27
(M þ 1).
4.6.7. 6-Methoxy-2-methyl-4-{4-[(4-methylpiperazin-1-yl)
methyl]-1H-1,2,3-triazol-1-yl}quinoline (5g)
4.6.12. 4-(4-((4-(2-Fluorophenyl)piperazin-1-yl)methyl)-1H-1,2,3-
Appearance e pale brown solid; IR (KBr, cmꢁ1
)
nmax: 3090
(CeH), 1450 (C]C), 1498 (CeH), 1210 (CeO), 1140 (CeN); 1H NMR
(CDCl3-300 MHz)
triazol-1-yl)-6-methoxy-2-methylquinoline (5l)
Appearance
e
yellow solid; 1H NMR (CDCl3-300 MHz)
d
ppm ¼ 2.33 (s, 3H, CH3), 2.53 (m, 4H, NCH2),
d
ppm ¼ 2.55e2.58 (m, 1H, NCH2), 2.69e2.71 (m, 4H, NCH2), 2.79 (s,
2.58 (m, 4H, NCH2), 2.68 (s, 3H, CH3), 2.79 (s, 3H, CH3), 3.86 (s, 3H,
OCH3), 3.88 (s, 3H, CH2), 7.10e7.18 (m, 5H, ArH) 7.21 (d, 1H,
J ¼ 2.7 Hz, ArH), 7.35 (s, 1H, ArH), 7.44 (dd, 1H, J ¼ 9.3 Hz, ArH), 8.03
1H, CH3), 3.86 (s, 3H, OCH3), 3.95 (s, 2H, CH2), 7.0e7.16 (m, 4H, ArH),
7.22 (d, 1H, J ¼ 2.7 Hz, ArH), 7.37 (s,1H, ArH), 7.43 (dd,1H, J ¼ 9.3 Hz,
ArH), 7.97 (s, 1H, ArH), 8.03 (d, 1H, J ¼ 9.3 Hz, ArH); 13C
d ppm
(s, 1H, ArH), 8.05 (d, 1H, J ¼ 9.3 Hz, ArH); 13C
d
ppm (CDCl3-
(CDCl3-75 MHz) ¼ 23.48, 48.98, 51.27, 56.60, 56.71, 107.18, 112.10,
114.18, 114.88, 117.02, 118.34, 121.30, 122.83, 125.05, 125.22, 126.24,
129.75, 134.27, 141.10, 141.77, 151.28, 156.12, 157.78, 162.73; LC/MS
(ESI-MS) m/z ¼ 433.21 (M þ 1).
75 MHz) ¼ 23.48, 34.26, 40.04, 49.06, 56.60, 57.20, 107.18, 112.10,
117.02, 118.34, 121.30, 126.74, 127.29,128.21, 129.75, 134.27, 141.10,
142.25, 144.77, 156.12, 162.73; LC/MS (ESI-MS) m/z ¼ 414.22
(M þ 1).
4.6.13. 4-(4-((4-(4-Fluorophenyl)piperazin-1-yl)methyl)-1H-1,2,3-
4.6.8. 6-Methoxy-2-methyl-4-(4-((4-methylpiperazin-1-yl)
triazol-1-yl)-6-methoxy-2-methylquinoline (5m)
methyl)-1H-1,2,3-triazol-1-yl)quinoline (5h)
Appearance- brown solid; IR (KBr, cmꢁ1
)
nmax: 3090 (CeH), 1450
(C]C), 1498 (CeH), 1210 (CeO), 1174 (CeF), 1140 (CeN); 1H NMR
(CDCl3-300 MHz)
Appearance
e
white solid; 1H NMR (CDCl3-300 MHz)
d
ppm ¼ 2.33 (s, 3H, CH3), 2.53e2.56 (m, 4H, NCH2), 2.58e2.60 (m,
d
ppm ¼ 2.55e2.58 (m, 1H, NCH2), 2.69e2.71 (m,
4H, NCH2), 2.79 (s, 3H, CH3), 3.86 (s, 3H, OCH3), 3.88 (s, 2H, CH2),
4H, NCH2), 2.79 (s, 1H, CH3), 3.86 (s, 3H, OCH3), 3.95 (s, 2H, CH2),
6.80e6.95 (m, 4H, ArH), 7.22 (d, 1H, J ¼ 2.7 Hz, ArH), 7.37 (s, 1H,
ArH), 7.43 (dd, 1H, J ¼ 9.3 Hz, ArH), 7.97 (s, 1H, ArH), 8.03 (d, 1H,
7.20 (d,1H, J ¼ 2.7 Hz, ArH), 7.38 (s,1H, ArH), 7.44 (dd,1H, J ¼ 9.3 Hz,
ArH), 7.99 (s, 1H, ArH), 8.03 (d, 1H, J ¼ 9.3 Hz, ArH); 13C
d ppm
(CDCl3-75 MHz) ¼ 23.48, 42.90, 48.98, 54.94, 55.04, 56.60, 107.18,
112.10, 117.02, 118.34, 121.30, 129.75, 134.27, 141.07, 141.10, 156.12,
162.73; LC/MS (ESI-MS) m/z ¼ 353.20 (M þ 1). Anal. Calcd for
C19H24N6O; C, 64.75; H, 6.86; N, 23.85; Found; C, 64.68; H, 6.89; N,
23.98.
J ¼ 9.3 Hz, ArH); 13C
d
ppm (CDCl3-75 MHz) ¼ 23.48, 48.98, 49.45,
56.60, 56.71, 107.18, 112.10, 114.27, 114.97, 117.02, 118.34, 121.30,
124.11, 124.29, 129.75, 134.27, 141.10, 141.77, 143.16, 143.23, 156.09,
156.12, 162.59, 162.73; LC/MS (ESI-MS) m/z ¼ 433.21 (M þ 1).
4.6.14. 6-Methoxy-4-(4-((4-(4-methoxyphenyl) piperazin-1-yl)
methyl)-1H-1,2,3-triazol-1-yl)-2-methylquinoline (5n)
4.6.9. 4-(4-((4-Ethylpiperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)-
6-methoxy-2-methyl quinoline (5i)
Appearance e off white solid; 1H NMR (CDCl3-300 MHz)
Appearance e off white solid; 1H NMR (CDCl3-300 MHz)
d
ppm ¼ 2.55e2.58 (m, 4H, NCH2), 2.69e2.71 (m, 4H, NCH2), 2.79 (s,
d
ppm ¼ 1.11 (t, 3H, J ¼ 7.2 Hz, CH3), 2.45 (q, 2H, J ¼ 7.2 Hz, CH2),
1H, CH3), 3.72 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.95 (s, 2H, CH2),
6.77 (d, 2H, J ¼ 8.5 Hz, ArH), 7.09 (d, 2H, J ¼ 8.5 Hz, ArH), 7.22 (d, 1H,
J ¼ 2.7 Hz, ArH), 7.37 (s, 1H, ArH), 7.43 (dd, 1H, J ¼ 9.3 Hz, ArH), 7.97
2.55e2.58 (m, 4H, NCH2), 2.69e2.71 (m, 4H, NCH2), 2.79 (s, 3H,
CH3), 3.85 (s, 3H, OCH3), 3.88 (s, 2H, CH2) 6.86e6.97 (m, 5H, ArH),
7.21 (d,1H, J ¼ 2.7 Hz, ArH), 7.38 (s,1H, ArH), 7.44 (dd,1H, J ¼ 9.3 Hz,
(s, 1H, ArH), 8.03 (d, 1H, J ¼ 9.3 Hz, ArH); 13C
d ppm (CDCl3-
ArH), 7.96 (s, 1H, ArH), 8.03 (d, 1H, J ¼ 9.3 Hz, ArH); 13C
d
ppm
75 MHz) ¼ 23.48, 48.98, 49.45, 55.20, 56.60, 56.71, 107.18, 112.10,
112.82, 117.02, 118.34, 121.30, 124.0, 129.75, 134.27, 139.97, 141.10,
141.77,156.12,157.24,162.73; LC/MS (ESI-MS) m/z ¼ 445.23 (M þ 1).
Anal. Calcd for C25H28N6O2; C, 67.55; H, 6.35; N, 18.91; Found; C,
67.61; H, 6.47; N, 18.85.
(CDCl3-75 MHz) ¼ 9.69, 23.48, 47.44, 48.98, 53.55, 55.44, 56.60,
107.18, 112.10, 117.02, 118.34, 121.30, 129.75, 134.27, 141.07, 141.10,
156.12, 162.73; LC/MS (ESI-MS) m/z ¼ 367.22 (M þ 1). Anal. Calcd
for C20H26N6O; C, 65.55; H, 7.15; N, 22.93; Found; C, 65.67; H, 7.20;
N, 22.86.
4.6.15. 6-Methoxy-2-methyl-4-(4-((4-p-tolylpiperazin-1-yl)
4.6.10. 1-(4-((1-(6-Methoxy-2-methylquinolin-4-yl)-1H-1,2,3-
triazol-4-yl)methyl) piperazin-1-yl)ethanone (5j)
methyl)-1H-1,2,3-triazol-1-yl)quinoline (5o)
Appearance e pale yellow solid; IR (KBr, cmꢁ1
)
nmax: 3090
(CeH), 1450 (C]C), 1498 (CeH), 1210 (CeO), 1140 (CeN); 1H NMR
(CDCl3-300 MHz),
Appearance e viscous liquid; IR (KBr, cmꢁ1
)
nmax: 2925 (CeH),
1645 (C]O), 1498 (CeH), 1210 (CeO), 1140 (CeN); 1H NMR (CDCl3-
300 MHz)
d
ppm ¼ 2.25 (s, 3H, CH3), 2.55e2.58 (m, 1H,
d
ppm ¼ 2.20 (s, 3H, CH3), 2.55e2.58 (m, 4H, NCH2),
NCH2), 2.69e2.71 (m, 4H, NCH2), 2.79 (s, 1H, CH3), 3.86 (s, 3H,
OCH3), 3.95 (s, 2H, CH2), 6.82 (d, 2H, J ¼ 8.6 Hz), 7.05 (d, 2H,
J ¼ 8.6 Hz, ArH), 7.22 (d, 1H, J ¼ 2.7 Hz, ArH), 7.37 (s, 1H, ArH), 7.43
(dd, 1H, J ¼ 9.3 Hz, ArH), 7.97 (s, 1H, ArH), 8.03 (d, 1H, J ¼ 9.3 Hz,
2.69e2.71 (m, 4H, NCH2), 2.79 (s, 3H, CH3), 3.85 (s, 3H, OCH3), 3.88
(s, 2H, CH2) 6.86e6.97 (m, 5H, ArH), 7.21 (d, 1H, J ¼ 2.7 Hz, ArH),
7.38 (s, 1H, ArH), 7.44 (dd, 1H, J ¼ 9.3 Hz, ArH), 7.96 (s, 1H, ArH), 8.03
(d, 1H, J ¼ 9.3 Hz, ArH); 13C
d
ppm (CDCl3-75 MHz) ¼ 21.09, 23.48,
ArH); 13C
d
ppm (CDCl3-75 MHz) ¼ 20.60, 23.48, 48.98, 49.45, 56.60,
44.67, 46.61, 48.98, 56.01, 56.60,107.18,112.10,117.02,118.34,121.30,
129.75, 134.27, 141.07, 141.10, 156.12, 162.73, 169.73; LC/MS (ESI-MS)
m/z ¼ 381.2 (M þ 1).
56.71, 107.18, 112.10, 112.84, 117.02, 118.34, 121.30, 128.52, 129.75,
134.27, 139.97, 141.10, 141.77, 144.14, 156.12, 162.73; LC/MS (ESI-MS)
m/z ¼ 429.23 (M þ 1).