Table 8
Analytical data of cinnoline and quinoline-carboxamides (1–45)
Compound NMR
HRMS (ESI, MH+,
m/z)
1
2
3
4
5
6
7
8
9
1H NMR (500 MHz, CDCl3) d ppm 0.93 (s, 9H) 1.00 (t, J = 7.3 Hz, 3H) 1.72 (sxt, J = 7.4 Hz, 2H) 3.23 (s, 2H) 3.57 (t, J = 7.2 Hz, 2H) 4.39 (s, 2H) 6.29 (br s, 2H) 7.38 (t, J = 7.6 Hz, 1H) 7.54 (d, 312.2070
J = 6.7 Hz, 1H) 7.69 (d, J = 8.2 Hz, 1H)
1H NMR (300 MHz, CDCl3) d ppm 0.97 (d, J = 6.6 Hz, 6H) 1.03 (t, J = 7.4 Hz, 3H) 1.69 (sxt, J = 7.3 Hz, 2H) 2.25 (dt, J = 13.5, 6.8 Hz, 1H) 3.28 (d, J = 7.3 Hz, 2H) 3.42–3.54 (m, 2H) 7.54–7.63 (m, 287.1867
2H) 7.66–7.75 (m, 1H) 8.59 (br s, 1H)
1H NMR (500 MHz, CDCl3) d ppm 1.00 (t, J = 7.5 Hz, 3H) 1.61–1.72 (m, 2H) 3.46 (q, J = 6.8 Hz, 2H) 7.39–7.46 (m, 1H) 7.50 (t, J = 7.5 Hz, 2H) 7.66–7.72 (m, 2H) 7.73 (d, J = 8.2 Hz, 1H) 7.78–7.83 307.1556
(m, 1H) 7.83–7.89 (m, 1H) 8.58 (br s, 1H)
1H NMR (300 MHz, CDCl3) d 8.55 (br, 1H), 7.87 (m, 1H), 7.75–7.64 (m, 2H), 7.23–7.07 (m, 3H), 3.44 (apparent quartet, J = 7.0 Hz, 2H), 2.35 (s, 3H), 2.01 (s, 3H), 1.64 (apparent sextet, J = 7.0 Hz, 335.1865
2H), 0.99 (t, J = 7.4 Hz, 3H)
1H NMR (500 MHz, CDCl3) d ppm 0.99 (t, J = 7.3 Hz, 3H) 1.64 (sxt, J = 7.2 Hz, 2H) 1.92 (s, 6H) 3.44 (q, J = 6.7 Hz, 2H) 7.15 (d, J = 7.3 Hz, 2H) 7.23 (t, J = 7.6 Hz, 1H) 7.61 (d, J = 7.0 Hz, 1H) 7.74 (t, 335.1865
J = 7.6 Hz, 1H) 7.89 (d, J = 8.6 Hz, 1H) 8.54 (br s, 1H)
1H NMR (300 MHz, CDCl3) d 8.58 (t, J = 5.0 Hz, 1H), 7.85 (dd, J = 8.3, 1.4 Hz, 1H), 7.79 (dd, J = 7.3, 1.4 Hz, 1H), 7.71 (dd, J = 8.1, 7.3 Hz, 1H), 7.50 (s, 1H), 7.48 (s, 2H), 7.39 (t, J = 7.9 Hz, 1H), 7.23 321.1710
(s, 1H), 3.46 (q, J = 6.7 Hz, 2H), 2.44 (s, 3H), 1.67 (sextet, J = 7.3 Hz, 2H), 1.00 (t, J = 7.4 Hz, 3H)
1H NMR (700 MHz, DMSO-d6) d 8.86 (br s, 1H), 8.62 (d, J = 7.91 Hz, 1H), 7.86 (t, J = 7.70 Hz, 1H), 7.79 (d, J = 7.14 Hz, 1H), 7.40 (t, J = 7.46 Hz, 1H), 7.36 (d, J = 7.34 Hz, 1H), 7.31 (t, J = 7.42 Hz, 321.1709
1H), 7.23 (d, J = 7.42 Hz, 1H), 3.30 (q, J = 6.74 Hz, 2H), 1.99 (s, 3H), 1.57 (sextet, J = 7.29 Hz, 2H), 0.89 (t, J = 7.46 Hz, 3H)
1H NMR (500 MHz, CDCl3) d ppm 0.99 (t, J = 7.5 Hz, 3H) 1.64 (sxt, J = 7.2 Hz, 2H) 2.03 (s, 3H) 2.39 (s, 3H) 3.44 (m, J = 6.1 Hz, 2H) 7.10 (d, J = 7.6 Hz, 1H) 7.13–7.21 (m, 2H) 7.64–7.77 (m, 2H) 335.1867
7.86 (d, J = 8.2 Hz, 1H) 8.55 (br s, 1H)
1H NMR (300 MHz, CDCl3) d ppm 1.00 (t, J = 7.4 Hz, 3H) 1.59–1.77 (m, 2H) 2.34–2.45 (m, 6H) 3.46 (q, J = 6.8 Hz, 2H) 7.06 (s, 1H) 7.26 (s, 2H) 7.66–7.74 (m, 1H) 7.74–7.79 (m, 1H) 7.80–7.87 335.1868
(m, 1H) 8.58 (br s, 1H)
10
11
1H NMR (300 MHz, CDCl3) d 8.56 (br m, 1H), 7.85 (a dd, J = 2.2, 7.6 Hz, 1H), 7.73 (m, 2H), 6.95 (m, 2H), 6.91 (m, 1H), 3.77 (s, 3H), 3.63 (s, 3H), 2.96 (m, 1H), 0.88 (m, 2H), 0.65 (m, 2H)
365.1607
1H NMR (500 MHz, DMSO-d6) d ppm 9.08–9.23 (m, 1H) 8.39 (dd, J = 8.24, 1.83 Hz, 1H) 7.66–7.79 (m, 2H) 7.00–7.08 (m, 1H) 6.92–7.00 (m, 1H) 6.80–6.89 (m, 1H) 4.23–4.70 (m, 1H) 3.73 (s, 393.1935
3H) 3.55 (s, 3H) 2.27–2.46 (m, 3H) 1.88–2.09 (m, 1H) 1.69–1.83 (m, 1H) 1.00–1.21 (m, 3H)
12
13
14
15
16
1H NMR 300 MHz, CDCl3) d 8.54 (t, J = 4.7 Hz, 1H), 7.86 (dd, J = 7.6, 2.2 Hz, 1H), 6.96 (t, J = 3.0 Hz, 1H), 6.96 (s, 1H), 6.93 (d, J = 1.9 Hz, 1H), 7.76–7.68 (m, 2H), 3.79 (s, 3H), 3.64 (s, 3H), 3.48 (q, 381.1922
J = 6.6 Hz, 2H), 1.61 (quintet, J = 7.2 Hz, 2H), 1.43 (sextet, J = 7.3 Hz, 2H), 0.94 (t, J = 7.3 Hz, 3H)
1H NMR (300 MHz, CDCl3) d 8.59 (br, 1H), 7.89 (dd, J = 7.8 Hz, J0 = 1.9 Hz, 1H), 7.65–7.77 (m, 2H), 6.85–7.20 (m, 3H), 3.79 (s, 3H), 3.64 (s, 3H), 3.35–3.55 (m, overlapped with H2O), 1.64 (m, 367.1765
J = 7.3 Hz, 2H), 0.99 (t, J = 7.4 Hz, 3H)
1H NMR (500 MHz, DMSO-d6) d ppm 1.60–1.75 (m, 2H) 2.10–2.29 (m, 4H) 3.55 (s, 3H) 3.69–3.77 (m, 3H) 4.43–4.57 (m, 1H) 6.86 (d, J = 3.1 Hz, 1H) 6.97 (dd, J = 8.9, 3.1 Hz, 1H) 7.03 (d,
J = 9.2 Hz, 1H) 7.68–7.72 (m, 1H) 7.72–7.77 (m, 1H) 8.39 (dd, J = 8.1, 1.4 Hz, 1H) 9.20 (d, J = 8.2 Hz, 1H)
379.1763
1H NMR (300 MHz, CDCl3) d 8.51 (br t, J = 5.2 Hz, 1H), 7.86 (dd, J = 7.5, 2.1 Hz, 1H), 7.76–7.68 (m, 2H), 6.97–6.91 (m, 3H), 3.79 (s, 3H), 3.64 (s, 3H), 3.52 (dq, J = 5.7, 7.3 Hz, 2H), 1.26 (t,
J = 7.3 Hz, 3H)
353.1607
1H NMR (500 MHz, DMSO-d6) d ppm 8.76 (d, J = 8.24 Hz, 1H) 8.39 (dd, J = 8.24, 1.53 Hz, 1H) 7.66–7.79 (m, 2H) 7.00–7.06 (m, 1H) 6.93–6.99 (m, 1H) 6.85 (d, J = 3.05 Hz, 1H) 4.11–4.23 (m, 1H) 367.1763
3.73 (s, 3H) 3.55 (s, 3H) 1.22 (d, J = 6.71 Hz, 6H)
17
18
1H NMR (300 MHz, CDCl3) d ppm 2.47 (qt, J = 10.7, 6.9 Hz, 2H) 3.64 (s, 3H) 3.75 (q, J = 6.8 Hz, 2H) 3.79 (s, 3H) 6.89–6.98 (m, 3H) 7.64–7.81 (m, 2H) 7.83–7.90 (m, 1H) 8.71 (br s, 1H)
421.1481
1H NMR (500 MHz, DMSO-d6) d ppm 1.71 (quin, J = 6.5 Hz, 2H) 3.37–3.46 (m, 2H) 3.50 (q, J = 6.0 Hz, 2H) 3.55 (s, 3H) 3.68–3.78 (m, 3H) 4.50 (t, J = 5.2 Hz, 1H) 6.86 (d, J = 3.1 Hz, 1H) 6.97 (dd, 383.2
J = 8.9, 3.1 Hz, 1H) 7.03 (d, J = 9.0 Hz, 1H) 7.68–7.72 (m, 1H) 7.72–7.77 (m, 1H) 8.39 (d, J = 8.1 Hz, 1H) 9.10 (t, J = 5.8 Hz, 1H)
19
20
21
22
23
24
25
26
27
1H NMR (500 MHz, DMSO-d6) d 9.07 (d, J = 4.6 Hz, 1H), 8.39 (d, J = 8.2 Hz, 1H), 7.76–7.70 (m, 2H), 7.03 (d, J = 9.1 Hz, 1H), 6.97 (dd, J = 8.9, 3.0 Hz, 1H), 6.87 (d, J = 3.2 Hz, 1H), 3.73 (s, 3H), 3.55 339.1714
(s, 3H), 2.86 (d, J = 4.8 Hz, 3H)
1H NMR (500 MHz, DMSO-d6) d ppm 8.71 (d, J = 8.85 Hz, 1H) 8.40 (dd, J = 8.39, 1.68 Hz, 1H) 7.68–7.77 (m, 2H) 7.00–7.05 (m, 1H) 6.94–6.99 (m, 1H) 6.85 (d, J = 3.05 Hz, 1H) 3.94–4.05 (m, 1H) 381.1921
3.73 (s, 3H) 3.55 (s, 3H) 1.49–1.66 (m, 2H) 1.19 (d, J = 6.41 Hz, 3H) 0.88 (t, J = 7.48 Hz, 3H)
1H NMR (500 MHz, DMSO-d6) d ppm 8.83 (s, 1H) 8.40 (dd, J = 8.39, 1.68 Hz, 1H) 7.65–7.78 (m, 2H), 7.00–7.06 (m, 1H) 6.93–6.99 (m, 1H) 6.85 (d, J = 3.05 Hz, 1H) 3.73 (s, 3H) 3.55 (s, 3H) 2.38– 393.1924
2.47 (m, 2H) 1.95–2.10 (m, 2H) 1.77–1.89 (m, 2H) 1.53 (s, 3H)
1H NMR (500 MHz, DMSO-d6) d ppm 8.31 (dd, J = 8.4, 1.4 Hz, 1H) 7.64 (br s, 1H) 7.53 (dd, J = 7.0, 1.2 Hz, 1H) 7.44 (dd, J = 8.1, 7.2 Hz, 1H) 7.00 (d, J = 8.9 Hz, 1H) 6.90 (dd, J = 9.0, 3.2 Hz, 1H) 404.1968
6.75 (d, J = 3.1 Hz, 1H) 4.37 (s, 2H) 3.71 (s, 3H) 3.56 (s, 3H) 1.95 (s, 2H) 1.44 (s, 6H) 0.80 (t, J = 7.3 Hz, 3H)
1H NMR (500 MHz, DMSO-d6) d ppm 8.31 (d, J = 8.5 Hz, 1H) 7.52–7.56 (m, 1H) 7.46 (d, J = 7.2 Hz, 1H) 7.01 (d, J = 9.2 Hz, 1H) 6.91 (dd, J = 8.9, 3.1 Hz, 1H) 6.76 (d, J = 3.1 Hz, 1H) 4.56 (quin, 404.1965
J = 7.7 Hz, 1H) 4.28 (s, 2H) 3.71 (s, 3H) 3.57 (s, 3H) 1.83 (d, J = 6.4 Hz, 2H) 1.52–1.76 (m, 6H)
1H NMR (300 MHz, CDCl3) d ppm 1.25 (t, J = 7.3 Hz, 3H) 3.53–3.72 (m, 5H) 3.80 (s, 3H) 4.32 (s, 2H) 6.36 (br s, 2H) 6.87–7.02 (m, 3H) 7.50 (dd, J = 8.3, 7.2 Hz, 1H) 7.68 (dd, J = 7.2, 1.5 Hz, 1H) 364.1659
7.84 (dd, J = 8.3, 1.5 Hz, 1H)
1H NMR (300 MHz, CDCl3) d ppm 3.15 (s, 3H) 3.66 (s, 3H) 3.80 (s, 3H) 4.32 (s, 2H) 6.35 (br s, 2H) 6.85–7.02 (m, 3H) 7.50 (dd, J = 8.3, 7.2 Hz, 1H) 7.68 (dd, J = 7.0, 1.3 Hz, 1H) 7.84 (dd, J = 8.3, 350.1498
1.1 Hz, 1H)
1H NMR (500 MHz, DMSO-d6) d 8.32 (d, J = 8.2 Hz, 1H), 7.58 (br s, 2H), 7.55 (dd, J = 7.2, 1.2 Hz, 1H), 7.46 (dd, J = 8.3, 7.1 Hz, 1H), 7.02 (d, J = 9.0 Hz, 1H), 6.91 (dd, J = 9.0, 3.1 Hz, 1H), 6.78 (d, 390.1808
J = 3.1 Hz, 1H), 4.72 (q, J = 8.6 Hz, 1H), 4.40 (s, 2H), 3.72 (s, 3H), 3.56 (s, 3H), 2.31 m, 2H), 2.11m 2H), 1.68 (m, 2H)
1H NMR (500 MHz, DMSO-d6) d ppm 8.27–8.35 (m, 1H) 7.55 (dd, J = 7.2, 1.4 Hz, 1H) 7.42–7.49 (m, 1H) 7.01 (d, J = 8.8 Hz, 1H) 6.91 (dd, J = 9.0, 3.2 Hz, 1H) 6.77 (d, J = 3.1 Hz, 1H) 4.82–4.96 (m, 406.2124
0.5H) 4.50–4.61 (m, 0.5H) 4.42 (s, 1H) 4.38 (s, 1H) 3.68–3.77 (m, 3H) 3.54–3.60 (m, 3H) 2.38–2.51 (m, 0.5H) 2.24–2.33 (m, 2H) 1.99–2.12 (m, 0.5H) 1.76–1.95 (m, 2H) 1.18 (d, J = 7.0 Hz, 1.5H)
1.07 (d, J = 6.4 Hz, 1.5H)
28
1H NMR (500 MHz, DMSO-d6) d 8.31 (dd, J = 8.3, 1.0 Hz, 1H), 7.60 (br s, 1H), 7.54 (dd, J = 7.1, 1.3 Hz, 1H), 7.46 (dd, J = 8.4, 7.4 Hz, 1H), 7.00 (d, J = 9.1 Hz, 1H), 6.90 (dd, J = 8.7, 3.0 Hz, 1H), 6.76 376.1654