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A. Drabczynska et al. / Bioorg. Med. Chem. 12 (2004) 4895–4908
4899
Table 3. Spectroscopic data of compounds 1–22
Compd
IR m (cmꢁ1
)
UV kmax, loge
1H NMR d (ppm)
1
2954-Alkyl, 1709-CO (pos. 2), 1658-CO (pos. 4),
1209-COC, 742-CH2
280
5.02
3.17 (s, 3H, N3CH3), 3.31 (s, 3H, N1CH3), 4.30 (t,
J=7.98Hz, 2H, N5CH2), 5.13 (t, J=8.02Hz, 2H,
CH2)
Ref. 18
2
3
4
5
2955-Alkyl, 1710-CO (pos. 2), 1661-CO (pos. 4),
1141-COC, 744-CH2
280
5.09
278
4.92
280
4.99
280
4.98
2955-Alkyl, 1711-CO (pos. 2), 1657-CO (pos. 4),
1208-COC, 744-CH2
Ref. 18
Ref. 18
2952, 2884-alkyl, 1713-CO (pos. 2), 1656-CO
(pos. 4), 1052-COC, 742-CH2
3407-OH, 2956-alkyl, 1710-CO (pos. 2), 1655-CO
(pos. 4), 1081-COC, 746-CH2
3.16 (s, 3H, N3CH3), 3.30 (s, 3H, N1CH3), 3.62–
3.84 (2m, 2H, N5CH2), 4.07–4.39 (2m, 2H,
CH2OH), 5.30 (t, J=5.5Hz, 1H, OH), 5.46–5.61
(m, 1H, CH)
6
7
2959, 2876-alkyl, 1715-CO (pos. 2), 1655-CO
(pos. 4), 1126-COC, 743-CH2
280
5.06
1.01 (t, J=7.43Hz, 3H, (CH2)2CH3), 1.45–1.52
(m, 2H, CH2–CH2CH3), 1.7–2.02 (2m, 2H,
CH2CH2CH3), 3.37 (s, 3H, N3CH3), 3.50 (s, 3H,
N1CH3), 3.99 (q, J=7.7Hz, 1H, N5CH2), 4.48 (q,
J=8.25Hz, 1H, N5CH2), 5.34–5.44 (m, 1H, CH)
0.91 (t, J=7.15Hz, 3H, (CH2)3CH3), 1.35–1.53
(m, 4H, CH2–(CH2)2CH3), 1.81–2.02 (2m, 2H,
CH2(CH2)2CH3), 3.34 (s, 3H, N3CH3), 3.47 (s,
3H, N1CH3), 3.95–4.01 (q, J=7.7Hz, 1H,
N5CH2), 4.43–4.49 (q, J=7.7Hz, 1H, N5CH2),
5.32–5.41 (m, 1H, CH)
2958, 2932-alkyl, 1715-CO (pos. 2), 1655-CO
(pos. 4), 1126-COC, 743-CH2
280
4.97
8
9
2956, 2929, 2858-alkyl, 1715-CO (pos. 2),
1655-CO (pos. 4), 1086-COC, 744-CH2
280
5.06
0.88 (t, J=6.74Hz, 3H, (CH2)5CH3), 1.29–1.54
(m, 8H, CH2–(CH2)4CH3), 1.81–2.01 (2m, 2H,
CH2(CH2)4CH3), 3.37 (s, 3H, N3CH3), 3.50 (s,
3H, N1CH3), 3.95–4.02 (dd, J=7.70Hz, 1H,
N5CH2), 4.45–4.50 (dd, J=7.57Hz, 1H, N5CH2),
5.38–5.42 (m, 1H, CH)
2956, 2926, 2856-alkyl, 1715-CO (pos. 2),
1654-CO (pos. 4), 1051-COC, 743-CH2
280
5.06
0.87 (t, J=6.74Hz, 3H, (CH2)7CH3), 1.26–1.54
(m, 12H, CH2(CH2)6CH3), 1.94–2.01 (m, 1H,
CH2(CH2)6CH3), 1.94–2.06 (m, 1H,
CH2(CH2)6CH3), 3.37 (s, 3H, N3CH3), 3.51 (s,
3H, N1CH3), 3.97–4.02 (q, J=7.70Hz, 1H,
N5CH2), 4.45–4.51 (q, J=8.11Hz, 1H, N5CH2),
5.33–5.41 (m, 1H, CH)
10
11
3075-Alkenyl, 2954-alkyl, 1714-CO (pos. 2),
1655-CO (pos. 4), 1210-COC, 744-CH2
280
5.10
1.92–2.34 (3·m, 4H, (CH2)2), 3.38 (s, 3H,
N3CH3), 3.51 (s, 3H, N1CH3), 4.01 (q, J=7.56Hz,
1H, N5CH2), 4.49 (t, J=8.94Hz, 1H, N5CH2),
5.06–5.14 (m, 2H, CH2@CH), 5.35–5.45 (m, 1H,
CH2@CH), 5.75–5.88 (m, 1H, CH)
1.44–2.12 (m, 8H, (CH2)4), 3.38 (s, 3H, N3CH3),
3.51 (s, 3H, N1CH3), 4.00 (q, J=7.70Hz, 1H,
N5CH2), 4.45–4.50 (m, 1H, N5CH2), 4.95–5.04 (m,
2H, CH2@CH), 5.33–5.43 (m, 1H, CH2@CH),
5.61–5.84 (m, 1H, CH)
3077-Alkenyl, 2991, 2859-alkyl, 1713-CO (pos. 2),
1659-CO (pos. 4), 1097-COC, 744-CH2
280
5.01
12
13
2955–2873-Alkyl, 1706-CO (pos. 2), 1658-CO
(pos. 4), 1199-COC, 744-CH2
280
4.93
1.38–2.00 (m, 6H, cyclohexyl), 2.39–2.45 (m, 1H,
cyclohexyl), 2.87–2.92 (m, 1H, cyclohexyl), 3.38 (s,
3H, N3CH3), 3.52 (s, 3H, N1CH3), 3.65–3.74 (dt,
1H, N5CH), 4.47–4.56 (dt, 1H, OCH)–
3.14–3.21 (m, 1H, CH2), 3.31 (d, J=6.33Hz, 1H,
CH2), 3.36 (s, 3H, N3CH3), 3.51 (s, 3H, N1CH3),
4.10 (q, J=7.70Hz, 1H, N5CH2), 4.39 (q,
J=8.25Hz, 1H, N5CH2), 5.54–5.65 (m, 1H, CH),
7.37 (m, 5H, phenyl)
3025-Phenyl, 2948-alkyl, 1703-CO (pos. 2),
1653-CO (pos. 4), 1059-COC, 746-CH2
280
4.97
14
15
2971, 2934, 2867-alkyl, 1714-CO (pos. 2),
1655-CO (pos. 4), 1149-COC, 744-CH2
280
4.76
1.12–1.15 (m, 6H, 2CH3), 3.38 (s, 3H, N3CH3),
3.51 (s, 3H, N1CH3), 3.61–3.73 (m, 1H,
CH(CH3)2), 3.75–3.83 (m, 2H, N5CH2), 4.30–4.45
(m, 2H, CH2O), 5.42–5.50 (m, 1H, CH)
0.84 (q, J=3.03Hz, 6H, 2CH3), 1.80–1.87 (m, 1H,
CH(CH3)2), 3.28 (d, J=6.60Hz, 2H, CH2CH),
3.38 (s, 3H, N3CH3), 3.51 (s, 3H, N1CH3), 3.78
(m, 2H, N5CH2), 4.31–4.44 (m, 2H, CH2O),
5.43–5.51 (m, 1H, CH)
2957, 2874-alkyl, 1714-CO (pos. 2), 1672-CO
(pos. 4), 1120-COC, 742-CH2
280
4.97
(continued on next page)