R. Junek et al. / European Journal of Medicinal Chemistry 44 (2009) 332e344
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Table 4
1H NMR spectra of esters 25be35c
Compound
1H NMR spectrum
25b
1.37 (d, J ¼ 7.2, 3H); 2.16 (m, 2H); 2.74 (t, J ¼ 7.2; 2H); 2.85 (s, 1.5H); 2.90 (s, 1.5H); 3.37 (s, 1H); 3.50 (t, J ¼ 7.5, 1H); 3.59 (t, J ¼ 7.6,
1H); 3.57 (s, 1H); 3.58 (s, 3H); 3.73 (q, J ¼ 7.1, 1H); 4.12 (m, 4H); 6.84e6.94 (m, 4H); 7.01 (d, J ¼ 8.7, 1H); 7.09 (d, J ¼ 8.6, 1H); 7.17e
7.32 (m, 7H)
25c
26b
26c
27b
27c
28b
1.47 (d, J ¼ 7.2, 3H); 1.96 (m, 4H); 2.73 (t, J ¼ 7.3, 1H); 2.83 (t, J ¼ 7.4, 1H); 2.85 (s, 1.5H); 2.97 (s, 1.5H); 3.39 (s, 1H); 3.50 (t, J ¼ 7.4,
1H); 3.59 (t, J ¼ 7.4, 1H); 3.61 (s, 1H); 3.65 (s, 3H); 3.67 (q, J ¼ 7.1, 1H); 4.02 (m, 4H); 6.82e6.86 (m, 4H); 7.05e7.25 (m, 9H)
1.46 (d, J ¼ 7.3, 3H); 2.28 (m, 2H); 2.73 (t, J ¼ 7.3, 1H); 2.85 (s, 1.5H); 2.86 (t, J ¼ 7.5, 1H); 2.97 (s, 1.5H); 3.38 (s, 1H); 3.47 (t, J ¼ 7.4,
1H); 3.59 (t, J ¼ 7.6, 1H); 3.61 (s, 1H); 3.63 (q, J ¼ 7.2, 1H); 3.65 (s, 3H); 4.19 (m, 4H); 6.81e6.91 (m, 3H); 7.03e7.31 (m, 9H)
1.45 (d, J ¼ 7.0, 3H); 2.02 (m, 4H); 2.71 (t, J ¼ 7.4, 1H); 2.83 (t, J ¼ 7.2, 1H); 2.85 (s, 1.5H); 2.97 (s, 1.5H); 3.39 (s, 1H); 3.50 (t, J ¼ 7.3,
1H); 3.60 (t, J ¼ 7.4, 1H); 3.62 (s, 1H); 3.63 (q, J ¼ 7.1, 1H); 3.66 (s, 3H); 4.08 (m, 4H); 6.79e6.87 (m, 3H); 7.01e7.29 (m, 9H)
2.24 (m, 2H); 2.62 (t, J ¼ 7.4, 2H); 2.74 (t, J ¼ 7.4, 1H); 2.84 (t, J ¼ 7.4, 1H); 2.89 (s, 1.5H); 2.90 (t, J ¼ 7.5, 2H); 2.97 (s, 1.5H); 3.38 (s,
1H); 3.50 (t, J ¼ 7.6, 1H); 3.59 (t, J ¼ 7.7, 1H); 3.61 (s, 1H); 3.66 (s, 3H); 4.13 (m, 4H); 6.84 (m, 4H); 7.02e7.34 (m, 9H)
1.96 (m, 4H); 2.60 (t, J ¼ 7.2, 2H); 2.80 (t, J ¼ 7.1, 1H); 2.87 (t, J ¼ 7.3, 1H); 2.89 (s, 1.5H); 2.90 (t, J ¼ 7.1, 2H); 2.98 (s, 1.5H); 3.39 (s,
1H); 3.53 (m, 2H); 3.62 (s, 1H); 3.66 (s, 3H); 3.99 (m, 4H); 6.81e6.86 (m, 4H); 7.02e7.30 (m, 9H)
2.21 (m, 2H); 2.63 (t, J ¼ 7.7, 2H); 2.74 (t, J ¼ 7.5, 1H); 2.85 (t, J ¼ 7.4, 1H); 2.86 (s, 1.5H); 2.89 (t, J ¼ 7.8, 2H); 2.97 (s, 1.5H); 3.39 (s,
1H); 3.50 (t, J ¼ 7.3, 1H); 3.60 (t, J ¼ 7.4, 1H); 3.61 (s, 1H); 3.67 (s, 3H); 3.82 (s, 3H); 4.16 (m, 4H); 6.72 (m, 2H); 6.84 (m, 3H); 7.04e
7.26 (m, 7H)
28c
29b
29c
1.98 (m, 4H); 2.64 (t, J ¼ 8.2, 2H); 2.73 (t, J ¼ 7.3, 1H); 2.84 (t, J ¼ 7.4, 1H); 2.86 (s, 1.5H); 2.86 (t, J ¼ 8.1, 2H); 2.97 (s, 1.5H); 3.39 (s,
1H); 3.50 (t, J ¼ 7.2, 1H); 3.60 (t, J ¼ 7.4, 1H); 3.61 (s, 1H); 3.67 (s, 3H); 3.84 (s, 3H); 4.05 (m, 4H); 6.73 (m, 2H); 6.81e6.87 (m, 3H);
7.10e7.30 (m, 7H)
1.13 (d, J ¼ 6.7, 3H); 2.23 (m, 2H); 2.59 (t, J ¼ 7.6, 2H); 2.67 (t, J ¼ 7.4, 1H); 2.76 (t, J ¼ 7.3, 1H); 2.83 (s, 1.5H); 2.86 (q, J ¼ 6.9, 1H);
2.97 (s, 1.5H); 3.38 (s, 1H); 3.50 (t, J ¼ 7.5, 1H); 3.58 (t, J ¼ 7.5, 1H); 3.62 (s, 1H); 3.64 (s, 3H); 4.13 (m, 4H); 6.80e6.87 (m, 4H); 7.04e
7.25 (m, 9H)
1.13 (d, J ¼ 6.6, 3H); 1.95 (m, 4H); 2.59 (d, J ¼ 6.9, 1H); 2.65 (d, J ¼ 6.7, 1H); 2.74 (t, J ¼ 7.0, 1H); 2.80 (t, J ¼ 7.2, 1H); 2.74 (s, 1.5H);
2.90 (q, J ¼ 6.9, 1H); 2.95 (s, 1.5H); 3.35 (s, 1H); 3.49 (t, J ¼ 7.3, 1H); 3.57 (t, J ¼ 7.4, 1H); 3.59 (s, 1H); 3.62 (s, 3H); 4.01 (m, 4H); 6.78e
6.83 (m, 4H); 7.04e7.27 (m, 9H)
30a
30b
1.95 (m, 2H); 2.31 (t, J ¼ 7.4, 2H); 2.54 (t, J ¼ 7.5, 2H); 2.74 (t, J ¼ 7.3, 1H); 2.84 (t, J ¼ 7.3, 1H); 2.85 (s, 1.5H); 2.97 (s, 1.5H); 3.39 (s,
1H); 3.50 (t, J ¼ 7.4, 1H); 3.60 (t, J ¼ 7.5, 1H); 3.60 (s, 1H); 3.66 (s, 3H); 4.30 (m, 4H); 6.86e7.05 (m, 4H); 7.09e7.29 (m, 9H)
1.93 (m, 2H); 2.23 (m, 2H); 2.31 (t, J ¼ 7.4, 2H); 2.58 (t, J ¼ 7.5, 2H); 2.69 (t, J ¼ 7.4, 1H); 2.76 (t, J ¼ 7.5, 1H); 2.83 (s, 1.5H); 2.97 (s,
1.5H); 3.38 (s, 1H); 3.50 (t, J ¼ 7.5, 1H); 3.59 (t, J ¼ 7.4, 1H); 3.60 (s, 1H); 3.65 (s, 3H); 4.12 (m, 4H); 6.80e6.85 (m, 4H); 7.03e7.26 (m,
9H)
30c
31a
1.86e2.04 (m, 6H); 2.31 (t, J ¼ 7.5, 2H); 2.58 (t, J ¼ 7.5, 2H); 2.74 (t, J ¼ 7.3, 1H); 2.83 (t, J ¼ 7.1, 1H); 2.86 (s, 1.5H); 2.97 (s, 1.5H);
3.39 (s, 1H); 3.51 (t, J ¼ 7.5, 1H); 3.60 (t, J ¼ 7.4, 1H); 3.61 (s, 1H); 3.66 (s, 3H); 4.00 (m, 4H); 6.80e6.86 (m, 4H); 7.06e7.28 (m, 9H)
1.17 (d, J ¼ 7.0, 3H); 1.62 (m, 1H); 1.97 (m, 1H); 2.48 (m, 1H); 2.58 (t, J ¼ 5.0, 2H); 2.74 (t, J ¼ 7.0, 1H); 2.83 (t, J ¼ 7.1, 1H); 2.86 (s,
1.5H); 2.97 (s, 1.5H); 3.39 (s, 1H); 3.50 (t, J ¼ 7.5, 1H); 3.61 (t, J ¼ 7.5, 1H); 3.62 (s, 1H); 3.67 (s, 3H); 4.28 (m, 4H); 6.88e6.91 (m, 4H);
7.08e7.26 (m, 9H)
31b
31c
1.16 (d, J ¼ 7.0, 3H); 1.67 (m, 1H); 1.92 (m, 1H); 2.20 (m, 2H); 2.43 (m, 1H); 2.53 (t, J ¼ 7.9, 2H); 2.73 (t, J ¼ 7.3, 1H); 2.79 (t, J ¼ 7.4,
1H); 2.80 (s, 1.5H); 2.94 (s, 1.5H); 3.36 (s, 1H); 3.47 (t, J ¼ 7.4, 1H); 3.57 (t, J ¼ 7.5, 1H); 3.58 (s, 1H); 3.64 (s, 3H); 4.10 (m, 4H); 6.77e
6.87 (m, 4H); 7.04e7.26 (m, 9H)
1.18 (d, J ¼ 7.0, 3H); 1.70 (m, 1H); 1.96 (m, 5H); 2.55 (m, 1H); 2.58 (t, J ¼ 7.9, 2H); 2.74 (t, J ¼ 7.3, 1H); 2.84 (t, J ¼ 7.5, 1H); 2.85 (s,
1.5H); 2.97 (s, 1.5H); 3.39 (s, 1H); 3.50 (t, J ¼ 7.4, 1H); 3.60 (t, J ¼ 7.5, 1H); 3.61 (s, 1H); 3.67 (s, 3H); 4.00 (m, 4H); 6.80e6.86 (m, 4H);
7.06e7.26 (m,)
32a
33a
33b
2.75 (t, J ¼ 6.8, 2H); 2.82 (m, 2H); 2.86 (s, 1.5H); 2.98 (s, 1.5H); 3.27 (t, J ¼ 6.7, 2H); 3.39 (s, 1H); 3.51 (t, J ¼ 7.6, 1H); 3.59 (t, J ¼ 7.4,
1H); 3.62 (s, 1H); 3.70 (s, 3H); 4.35 (m, 4H); 6.85 (m, 2H); 6.97 (m, 2H); 7.07e7.34 (m, 7H); 7.95 (m, 2H)
2.75 (t, J ¼ 6.8, 2H); 2.82 (m, 2H); 2.86 (s, 1.5H); 2.98 (s, 1.5H); 3.27 (t, J ¼ 6.7, 2H); 3.39 (s, 1H); 3.51 (t, J ¼ 7.6, 1H); 3.59 (t, J ¼ 7.4,
1H); 3.62 (s, 1H); 3.70 (s, 3H); 4.35 (m, 4H); 6.85 (m, 2H); 6.97 (m, 2H); 7.07e7.34 (m, 7H); 7.95 (m, 2H)
2.26 (m, 2H); 2.73 (m, J ¼ 7.2, 1H); 2.83 (m, J ¼ 7.2, 1H); 2.85 (s, 1.5H); 2.97 (s, 1.5H); 3.38 (s, 1H); 3.50 (t, J ¼ 7.5, 1H); 3.60 (t, J ¼ 7.4,
1H); 3.61 (s, 1H); 3.79 (s, 3H); 4.16 (m, 4H); 6.30 (d, J ¼ 16.2, 1H); 6.83e6.93 (m, 4H); 7.08e7.28 (m, 7H); 7.45 (d, J ¼ 8.6, 2H); 7.64 (d,
J ¼ 16.1, 1H)
33c
1.97 (m, 4H); 2.74 (t, J ¼ 7.2, 1H); 2.83 (t, J ¼ 7.0, 1H); 2.86 (s, 1.5H); 2.97 (s, 1.5H); 3.39 (s, 1H); 3.51 (t, J ¼ 7.5, 1H); 3.60 (t, J ¼ 7.5,
1H); 3.61 (s, 1H); 3.79 (s, 3H); 4.03 (m, 4H); 6.30 (d, J ¼ 16.0, 1H); 6.82e6.92 (m, 4H); 7.07e7.29 (m, 7H); 7.46 (m, 2H); 7.65 (d,
J ¼ 16.0, 1H)
34a
34b
2.75 (t, J ¼ 7.3, 1H); 2.82 (t, J ¼ 7.5, 1H); 2.83 (s, 1.5H); 2.97 (s, 1.5H); 3.38 (s, 1H); 3.51 (t, J ¼ 7.3, 1H); 3.57 (t, J ¼ 7.4, 1H); 3.62 (s,
1H); 3.80 (s, 3H); 3.88 (s, 3H); 4.37 (m, 4H); 6.35 (d, J ¼ 16.0, 1H); 6.87e6.90 (m, 3H); 7.04e7.30 (m, 9H); 7.63 (d, J ¼ 16.0, 1H)
2.30 (m, 2H); 2.67 (t, J ¼ 7.3, 1H); 2.79 (t, J ¼ 7.4, 1H); 2.85 (s, 1.5H); 2.97 (s, 1.5H); 3.37 (s, 1H); 3.53 (t, J ¼ 7.4, 1H); 3.59 (t, J ¼ 7.4,
1H); 3.61 (s, 1H); 3.80 (s, 3H); 3.88 (s, 3H); 4.16 (m, 4H); 6.27 (d, J ¼ 15.9, 1H); 6.80e6.91 (m, 3H); 7.02e7.34 (m, 7H); 7.62 (d,
J ¼ 16.0, 1H)
34c
35a
2.01 (m, 2H); 2.75 (t, J ¼ 7.4, 1H); 2.83 (t, J ¼ 7.3, 1H); 2.86 (s, 1.5H); 2.98 (s, 1.5H); 3.39 (s, 1H); 3.50 (t, J ¼ 7.4, 1H); 3.61 (t, J ¼ 7.5,
1H); 3.62 (s, 1H); 3.80 (s, 3H); 3.84 (s, 3H); 4.12 (m, 4H); 6.31 (d, J ¼ 15.9, 1H); 6.83e6.86 (m, 3H); 7.04e7.27 (m, 9H); 7.64 (d,
J ¼ 15.9, 1H)
1.57 (d, J ¼ 7.2, 3H); 2.30 (m, 2H); 2.73 (t, J ¼ 7.3, 1H); 2.80 (t, J ¼ 7.3, 1H); 2.84 (s, 1.5H); 2.96 (s, .5H); 3.38 (s, 1H); 3.49 (t, J ¼ 7.3,
1H); 3.59 (t, J ¼ 7.4, 1H); 3.61 (s, 1H); 3.66 (s, 3H); 3.86 (q, J ¼ 7.2, 1H); 4.17 (m, 2H); 4.25 (m, 2H); 6.86 (m, 2H); 7.02e7.38 (m, 10H);
7.61e7.65 (m, 3H)
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