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E. Martini et al. / Bioorg. Med. Chem. 16 (2008) 1431–1443
Table 6. Spectroscopic data for compounds reported in Table 3
N
[1H] NMR (CDCl3) d:
[
13C] NMR (CDCl3) d:
1a
1.16 (t, 3H, J = 7.6 Hz); 2.34–2.38 (m, 2H); 3.26–3.28 (m, 2H);
3.63 (t, J = 5.2 Hz, 33.3%) and 3.78 (t, J = 5.2 Hz, 66.6%) (2H);
4.21 (s, 66.6%) and 4.34 (s, 33.3%) (2H); 4.63 (s, 2H); 7.25–7.37
(m, 5H) ppm
26.53, 29.69, 38.72, 42.46, 45.21, 45.63, 46.32, 48.93, 49.81,
50.10, 127.62, 127.77, 127.90, 128.24, 128.39, 135.91, 164.68,
172.23 ppm
2a
2.10 (s, 33.3%) and 2.12 (s, 66.6%) (3H); 3.25–3.32 (m, 2H); 3.63
(t, J = 4.0 Hz, 33.3%) and 3.76 (t, J = 4.0 Hz, 66.6%) (2H); 4.21
(s, 66.6%) and 4.32 (s, 33.3%) (2H); 4.63 (s, 66.6%) and 4.64 (s,
33.3%) (2H); 7.25–7.33 (m, 5H) ppm
21.10, 21.34, 38.58, 43.38, 45.16, 45.56, 46.16, 49.68, 49.83,
50.11, 127.78, 127.89, 127.93, 128.24, 128.85, 135.86, 136.03,
164.57, 165.57, 168.62, 168.95 ppm
3
4
5
6
0.93 (t, 3H, J = 7.6 Hz); 1.61 (q, 2H, J = 7.6 Hz); 3.37–3.48 (m,
4H); 3.89–4.02 (m, 2H), 4.08–4.25 (m, 2H), 7.44 (s, 5H) ppm
0.89 (t, 3H, J = 6.8 Hz); 1.54 (q, 2H, J = 6.8 Hz); 3.31–3.42 (m,
6H); 3.71 (s, 2H); 7.25–7.28 (m, 2H); 7.82–7.85 (m, 2H) ppm
1.10 (t, 3H, J = 7.2 Hz); 3.32–3.35 (m, 2H); 3.39–3.44 (m, 4H);
3.70 (s, 2H); 7.18–7.33 (m, 2H); 7.81–7.83 (m, 2H) ppm
1.18 (t, 3H, J = 7.2 Hz); 1.38 (d, 6H, J = 6.8 Hz); 3.24 (sept, 1H,
J = 6.8 Hz); 3.43 (t, 2H, J = 5.2 Hz); 3.48 (q, 2H, J = 7.2 Hz);
3.62 (t, 2H, J = 5.2 Hz); 4.00 (s, 2H) ppm
11.22, 20.23, 29.68, 48.55, 48.61, 127.29, 128.53, 130.49, 170.13,
183.40 ppm
11.14, 20.09, 43.08, 46.14, 48.52, 48.75, 116.73 (d, J = 22 Hz),
130.58 (d, J = 9 Hz); 163.34, 165.59 (d, J = 255 Hz) ppm
11.98, 41.66, 43.05, 45.46, 48.78, 116.72 (d, J = 23 Hz), 130.57
(d, J = 10 Hz), 131.16, 163.07, 165.58 (d, J = 255 Hz) ppm
12.07, 16.60, 41.83, 43.38, 46.67, 48.92, 53.76, 163.78 ppm
14
1.15 (t, 3H, J = 7.6 Hz); 1.27–1.46 (m, 2H); 1.49–1.58 (m, 1H);
1.75 (d, 2H, J = 13.2 Hz); 2.17–2.30 (m, 4H); 3.14 (t, 2H, J = 6.4
Hz); 3.80 (d, 2H, J = 13.2 Hz); 5.59 (br s, 1H); 7.20–7.28 (m,
2H); 7.76–7.80 (m, 2H) ppm
9.90, 29.10, 29.62, 35.37, 44.32, 46.00, 116.29 (d, J = 23 Hz),
130.24 (d, J = 9 Hz), 132.35, 165.17 (d, J = 254 Hz), 174.08 ppm
15
16
1.18 (t, 3H, J = 7.6 Hz); 1.15–1.32 (m, 1H); 1.74–1.87 (m, 4H);
2.23 (q, 2H, J = 7.6 Hz); 2.71–3.32 (br m, 4H); 3.71–3.78 (m,
1H); 4.69–4.82 (m, 1H); 5.59–5.68 (m, 1H); 7.41 (s, 5H) ppm
1.12–1.29 (m, 2H); 1.33 (d, 6H, J = 6.8 Hz); 1.61–1.71 (m, 1H);
1.77 (d, 2H, J = 12.8 Hz); 2.81–2.87 (m, 4H); 3.17 (quint, 1H,
J = 6.8 Hz); 3.84 (m, 2H, J = 12.8 Hz); 4.64–4.68 (m, 1H);
7.21–7.28 (m, 2H); 7.88–7.91 (m, 2H) ppm
10.01, 25.50, 28.60, 28.80, 36.54, 44.69, 119.83, 126.79, 128.47,
175.01, 178.23 ppm
16.75, 30.01, 36.15, 46.11, 48.33, 53.34, 116.43 (d, J = 22 Hz),
129.73 (d, J = 9 Hz), 136.05, 165.10 (d, J = 253 Hz) ppm
17
18
19
20
1.01–1.19 (m, 2H); 1.62–1.84 (m, 3H); 2.09 (s, 3H); 2.49–2.55
(m, 1H); 2.85–2.89 (m, 2H); 3.00–3.05 (m, 1H); 3.82–3.85 (m,
1H); 4.56–4.68 (m, 2H); 7.20–7.28 (m, 2H); 7.88–7.91 (m, 2H)
ppm
21.30, 23.50, 36.46, 37.21, 48.28, 116.36 (d, J = 23 Hz), 129.69
(d, J = 10 Hz), 138.20, 169.30 (d, J = 254 Hz), 175.17 ppm
1.01–1.18 (m, 2H); 1.12 (t, 3H, J = 7.4 Hz); 1.65–1.85 (m, 3H);
2.33 (q, 2H, J = 7.4 Hz); 2.46–2.58 (m, 1H); 2.81–2.84 (m, 2H);
2.93–2.99 (m, 1H); 3.75–3.86 (m, 1H); 4.58–4.61 (m, 1H);
7.17–7.26 (m, 2H); 7.77–7.90 (m, 2H) ppm
9.58, 26.56, 29.89, 36.57, 41.45, 45.21, 116.34 (d, J = 22 Hz),
129.69 (d, J = 9 Hz), 136.21, 165.01 (d, J = 253 Hz), 172.26 ppm
1.24–1.34 (m, 2H); 1.44–1.50 (m, 1H); 1.75 (d, 2H, J = 12.0 Hz);
2.22–2.28 (m, 2H); 2.83 (t, 2H, J = 6.8 Hz); 3.82 (m, 2H,
J = 12.0 Hz); 4.41–4.44 (m, 1H); 7.19–7.26 (m, 4H); 7.76–7.81
(m, 2H); 7.84–7.89 (m, 2H) ppm
28.43, 34.67, 45.57, 47.34, 116.63 (d, J = 23 Hz), 116.51 (d,
J = 24 Hz), 129.43 (d, J = 9 Hz), 130.53 (d, J = 10 Hz), 141.20,
141.70, 165.04 (d, J = 254 Hz), 165.15 (d, J = 255 Hz) ppm
1.19 (t, 3H, J = 7.6 Hz); 1.49–1.56 (m, 1H); 1.65–1.82 (m, 3H);
2.27 (q, 2H, J = 7.6 Hz); 2.63–2.68 (m, 1H); 2.85 (dd, 1H,
J = 11.8 Hz, J = 2.4 Hz); 3.26 (dd, 1H, J = 11.8 Hz, J = 4.0 Hz);
3.40–3.46 (m, 1H); 4.13–4.18 (br m, 1H); 6.01 (br s, 1H);
7.22–7.28 (m, 2H); 7.77–7.80 (m, 2H) ppm
9.87, 21.42, 28.20, 29.59, 43.99, 46.54, 50.51, 116.45 (d,
J = 23 Hz), 130.27 (d, J = 9 Hz), 132.20, 166.57 (d, J = 254 Hz),
173.76 ppm
21
22
1.48–1.69 (m, 1H); 1.72–1.83 (m, 3H); 2.03 (s, 3H); 2.60–2.65
(m, 1H); 2.82 (dd, 1H, J = 11.6 Hz, J = 2.8 Hz); 3.27 (dd, 1H,
J = 11.6 Hz, J = 4.4 Hz); 3.44–3.46 (m, 1H); 4.15–4.17 (m, 1H);
5.93–5.95 (m, 1H); 7.22–7.28 (m, 2H); 7.77–7.80 (m, 2H) ppm
1.27–1.38 (m, 1H); 1.33–1.38 (m, 6H); 1.55–1.63 (m, 1H);
1.69–1.78 (m, 2H); 1.84–1.98 (m, 1H); 2.87–2.92 (m, 1H);
2.96–3.07 (m, 1H); 3.09–3.22 (m, 2H); 3.62–3.74 (m, 1H);
4.57–4.59 (m, 1H); 7.22–7.36 (m, 2H); 7.78–7.81 (m, 2H) ppm
1.17 (t, 3 H, J = 7.6 Hz); 1.34–1.36 (m, 6H); 1.60–1.88 (m, 4H);
2.24 (q, 2H, J = 7.6 Hz); 3.09–3.23 (m, 2H); 3.34–3.44 (m, 2H);
3.59–3.63 (m, 1H); 4.00–4.06 (br m, 1H); 6.08 (br s, 1H) ppm
1.34–1.40 (m, 6H); 1.58–1.90 (m, 4H); 2.02 (s, 3H); 3.08–3.17
(m, 1H); 3.19–3.24 (m, 1H); 3.35 (dd, 1H, J = 13.2 Hz, J = 2.8
Hz); 3.45 (dd, 1H, J = 13.2 Hz, J = 3.6 Hz); 3.63–3.66 (m, 1H);
4.00–4.10 (m, 1H); 6.07 (br s, 1H) ppm
21.41, 23.37, 28.25, 44.01, 46.55, 50.56, 116.49 (d, J = 22 Hz),
130.29 (d, J = 10 Hz), 132.08, 165.29 (d, J = 254 Hz),
169.65 ppm
16.78, 21.61, 30.79, 46.27, 48.87, 51.81, 54.46, 116.54 (d, J = 22
Hz), 130.32 (d, J = 9 Hz), 133.02, 165.29 (d, J = 254 Hz) ppm
23
24
9.80, 16.67, 22.35, 28.51, 29.82, 44.13, 46.93, 50.56, 53.43,
173.50.
16.97, 22.57, 23.12, 28.65, 44.55, 46.78, 50.45, 53.35,
169.87 ppm
25
26
1.30 (d, 6H, J = 6.8 Hz); 1.50–1.67 (m, 2H); 1.72–1.75 (m, 2H);
3.00–3.04 (m, 1H); 3.14 (sept, 1H, J = 6.8 Hz); 3.27–3.44 (m,
4H); 5.31 (br s, 1H); 7.19–7.24 (m, 2H); 7.92–7.96 (m, 2H) ppm
1.38–1.83 (m, 4H); 2.11 (s, 3H); 3.21–3.50 (m, 4H); 3.68–3.70
(m, 1H); 4.84 (br s, 1H); 7.21–7.26 (m, 2H); 7.79–7.96 (m, 2H)
ppm
16.67, 22.94, 30.47, 46.49, 48.81, 51.20, 53.49, 116.44 (d, J = 22
Hz), 128.84 (d, J = 9 Hz), 133.10, 166.38 (d, J = 254 Hz) ppm
21.40, 22.11, 22.91, 30.37, 30.96, 41.59, 46.54, 46.61, 49.33,
49.71, 52.39, 116.44 (d, J = 22 Hz), 129.63 (d, J = 9 Hz), 137.81,
165.08 (d, J = 253 Hz), 169.83 ppm