C. Binisti et al. / European Journal of Medicinal Chemistry 36 (2001) 809–828
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Table III. IR and H-NMR data of compounds 24a–z.
Compound IR (film)
1H-NMR
24a
24b
24c
24d
24e
24f
24g
24h
24i
3380 (NH), 1594 (CꢀC Ar)
(CDCl3) 0.78 (t, 3H); 1.3 (br s, 4H); 1.55 (m, 2H); 1.82 (s, 1H exch with D2O);
2.40 (s, 3H); 2.70, 3, 3.60 (3m, 7H); 7.70 (d, 2H); 7.30 (d, 2H)
(CDCl3) 0.80 (t, 3H); 1.2 (br s, 6H); 1.60 (m, 2H); 1.70 (s, 1H exch with D2O);
2.35 (s, 3H); 2.30, 3, 3.60 (3m, 7H); 7.60 (d, 2H); 7.25 (d, 2H)
(CDCl3) 0.79 (t, 3H); 1.25 (br s, 12H); 1.50 (m, 2H); 1.30 (s, 1H exch with D2O);
2.34 (s, 3H); 2.7, 3, 3.6 (3m, 7H); 7.70 (d, 2H); 7.30 (d, 2H)
3350 (NH), 1596 (CꢀC Ar)
3340 (NH), 1595 (CꢀC Ar)
3380 (NH), 1595 (CꢀC Ar)
3288 (NH), 1598 (CꢀC Ar)
3300 (NH), 1598 (CꢀC Ar)
3360 (NH), 1595 (CꢀC Ar)
3387 (NH), 1587 (CꢀC Ar)
3340 (NH), 1590 (CꢀC Ar)
3350 (NH), 1580 (CꢀC Ar)
3340 (NH), 1590 (CꢀC Ar)
3388 (NH), 1591 (CꢀC Ar)
3432 (NH), 1596 (CꢀC Ar)
3410 (NH), 1586 (CꢀC Ar)
3325 (NH), 1585 (CꢀC Ar)
3321 (NH), 1583 (CꢀC Ar)
3372 (NH), 1586 (CꢀC Ar)
(CDCl3) 0.79 (t, 3H); 1.25 (br s, 16H); 1.50 (m, 2H); 1.30 (s, 1H exch with D2O);
2.35 (s, 3H); 2.7, 3, 3.6 (3m, 7H); 7.70 (d, 2H); 7.30 (d, 2H)
(CDCl3) 0.83 (t, 3H); 1.20 (br s, 22H); 1.60 (m, 2H); 2.38 (s, 3H); 2.15, 3, 3.6
(3m, 7H); 7.58 (d, 2H); 7.28 (d, 2H)
(CDCl3) 0.82 (t, 3H); 1.20 (br s, 26H); 1.55 (m, 2H); 1.90 (s, 1H exch with D2O);
2.40 (s, 3H); 2.25, 3, 3.80 (3m, 7H); 7.65 (d, 2H); 7.25 (d, 2H)
(CDCl3) 0.73 (t, 3H); 1.20 (br s, 30H); 1.50 (m, 2H); 1.35 (s, 1H exch with D2O);
2.45 (s, 3H); 2.55, 3, 3.60 (3m, 7H); 7.80 (d, 2H); 7.40 (d, 2H)
(CDCl3) 0.81 (t, 3H); 1.20 (br s, 12H); 1.55 (m, 2H); 1.52 (s, 1H exch with D2O);
2.60, 3, 3.75 (3m, 7H); 7.80 (d, 2H); 7.40 (m, 3H)
(CDCl3) 0.81 (t, 3H); 1.15 (br s, 12H); 1.50 (m, 2H); 1.49 (s, 1H exch with D2O);
2.60, 3.25, 3.70 (3m, 7H); 3 (s, 3H); 8 (m, 4H)
24j
(CDCl3) 0.82 (t, 3H); 1.12 (br s, 12H); 1.70 (m, 2H); 1.50 (s, 1H exch with D2O);
3.15, 3.90 (2m, 7H); 7.70 (d, 2H); 7.45 (d, 2H)
24k
24l
(CDCl3) 0.81 (t, 3H); 1.13 (br s, 12H); 1.70 (m, 2H); 1.60 (s, 1H exch with D2O);
3.10, 3.90 (2m, 7H); 3.80 (s, 3H); 7.70 (d, 2H); 6.80 (d, 2H)
(CDCl3) 0.81 (t, 3H); 1.15 (br s, 12H); 1.50 (m, 2H); 1.60 (s, 1H exch with D2O);
2.65, 3.15, 3.75 (3m, 7H); 3.80 (s, 3H); 7.85 (d, 1H); 7.45 (d, 1H); 6.90 (d, 2H)
(CDCl3) 0.81 (t, 3H); 1.20 (br s, 12H); 1.55 (m, 2H); 1.60 (s, 1H exch with D2O);
2.75, 3, 3.65 (3m, 7H); 3.80 (s, 3H); 7.30 (m, 3H); 7 (m, 1H)
24m
24n
24o
24p
24q
24r
24r%
(CDCl3) 0.80 (t, 3H); 1.20 (br s, 12H); 1.55 (m, 2H); 1.60 (s, 1H exch with D2O);
2.65, 3.15, 3.70 (3m, 7H); 3.85 (s, 9H); 7.00 (s, 2H)
(CDCl3) 0.82 (t, 3H); 1.15 (br s, 22H); 1.55 (m, 2H); 1.55 (s, 1H exch with D2O);
2.75, 3, 3.70 (3m, 7H); 7.75 (d, 2H); 7.45 (m, 3H)
(CDCl3) 0.81 (t, 3H); 1.15 (br s, 22H); 1.55 (m, 2H); 1.58 (s, 1H exch with D2O);
2.60, 3.25, 3.65 (3m, 7H); 3.00 (s, 3H); 8.00 (m, 4H)
(CDCl3) 0.82 (t, 3H); 1.20 (br s, 22H); 1.65 (m, 2H); 1.60 (s, 1H exch with D2O);
3.05, 3.80 (2m, 7H); 7.65 (d, 2H); 7.45 (d, 2H)
3335 (NH), 1574–1596
(CꢀC Ar)
(CDCl3) 0.82 (t, 3H); 1.20 (br s, 22H); 1.55 (m, 2H); 1.45 (s, 1H exch with D2O);
2.60, 3, 3.65 (3m, 7H); 3.8 (s, 3H); 7.70 (d, 2H); 6.85 (d, 2H)
3352 (NH), 1652 (CꢀC cis),
1579–1596 (CꢀC Ar)
(CDCl3) 0.83 (t, 3H); 1.24 (br s, 14H); 1.96 (m, 4H); 1.55 (m, 2H);1.50 (s, 1H
exch with D2O); 2.6 (m, 2H); 2.60, 3, 3.65 (3m, 7H); 3.80 (s, 3H); 5.30 (t, 2H);
7.70 (d, 2H); 6.80 (d, 2H)
24r¦
3351 (NH), 1674 (CꢀC trans), (CDCl3) 0.81 (t, 3H); 1.16 (br s, 14H); 1.88 (m, 4H); 1.50 (m, 2H);1.55 (s, 1H
1579–1596 (CꢀC Ar)
exch with D2O); 2.6 (m, 2H); 2.55, 3, 3.70 (3m, 7H); 3.75 (s, 3H); 5.31 (m, 2H);
7.65 (d, 2H); 6.80 (d, 2H)
24s
24t
24u
24v
3337 (NH), 1574 (CꢀC Ar)
(CDCl3) 0.83 (t, 3H); 1.20 (br s, 22H); 1.60 (m, 2H); 1.50 (s, 1H exch with D2O);
2.57, 3, 3.68 (3m, 7H); 7.60 (m, 4H)
3434–3324 (NH, NH2), 1601
(CꢀC Ar)
(CDCl3) 0.80 (t, 3H); 1.15 (br s, 22H); 1.50 (m, 2H); 1.50 (s, 3H exch with D2O);
2.60, 3, 3.70 (3m, 7H); 7.50 (d, 2H); 6.55 (d, 2H)
3330 (NH), 1580 (CꢀC Ar)
(CDCl3) 0.85 (t, 3H); 1.20 (br s, 22H); 1.55 (m, 2H); 1.45 (s, 1H exch with D2O);
2.75, 3.60 (2m, 7H); 3 (s, 6H); 7.60 (d, 2H); 6.6 (d, 2H)
3180–3300 (several bands,
(CDCl3) 0.80 (t, 3H); 1.17 (br s, 22H); 1.55 (m, 2H); 1.60 (s, 1H exch with D2O);
NH), 1690 (CꢀO), 1590–1612 2.20 (s, 3H); 2.67, 3.10, 3.68 (3m, 7H); 7.65 (d, 2H); 7.75 (d, 2H); 7.45 (s, 1H
(CꢀC Ar)
exch with D2O)
24w
24x
3175–3435 (several bands,
(CDCl3) 0.77 (t, 3H); 1.20 (br s, 22H); 1.50 (m, 2H); 1.25 (t, 3H); 1.50 (s, 1H
NH), 1730 (CꢀO), 1596–1617 exch with D2O); 2.63, 3, 3.60 (3m, 7H); 4.15 (q, 2H); 6.75 (s, 1H exch with D2O);
(CꢀC Ar)
7.40 (d, 2H); 7.60 (d, 2H)
3360 (NH), 1662 (CꢀO), 1593 (CDCl3) 0.80 (t, 3H); 1.20 (br s, 22H); 1.55 (m, 2H); 1.25 (t, 3H); 1.45 (s, 1H
(CꢀC Ar)
exch with D2O); 2.60, 3, 3.60 (3m, 7H); 4.15 (q, 2H); 6.75 (s, 1H exch with D2O);
7.40 (d, 3H); 7.75 (d, 6H); 8.00 (s, 1H exch with D2O)
24y
24z
3356 (NH), 1598 (CꢀC Ar)
3350 (NH), 1597 (CꢀC Ar)
(CDCl3) 0.82 (t, 3H); 1.20 (br s, 22H); 1.50 (m, 2H); 1.30 (d, 6H); 1.45 (s, 1H
exch with D2O); 2.6 (m, 1H); 2.75, 3.60 (2m, 7H); 7.70 (d, 2H); 7.25 (d, 2H)
(CDCl3) 0.9 (t, 3H); 1.25 (br s, 22H); 1.60 (m, 2H); 1.30 (t, 3H); 1.45 (s, 1H exch
with D2O); 2.6 (m, 2H); 2.80, 3.67 (2m, 7H); 7.70 (d, 2H); 7.30 (d, 2H)
exch, exchange.