A. Pau et al. / Il Farmaco 55 (2000) 439–447
443
Table 3
1H NMR spectra of compounds 6a–h, 7a–h and 8
Comp.
6a
1H NMR a
0.88 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.18 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3),1–2,2 (m, 9H cycloal.), 3.87
(m, 1H CHꢀN), 3.86 (s, 3H, 4%-OCH3), 3.92 (s, 6H, 3’-OCH3 and 5’-OCH3), 5.94 (d, 1H, NH), 6.98 (s, 2H, H-2% and H-6%).
0.85 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.16 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.86
(m, 1H, CHꢀN), 5.90 (d, 1H, NH), 7.40 (d, 2H, H-3% and H-5%), 7.70 (d, 2H, H-2% and H-6%).
6b
6c
0.87 (t, 3H, ꢀCH2 ꢀCH2ꢀCH3), 1.19 (m, 2H, ꢀCH2 ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.88
(m, 1H, CHꢀN), 6.01 (d, 1H, NH), 7.05 (t, 2H, H-3% and H-5%), 7.74 (dd, 2H, H-2% and H-6%).
0.87 (t, 3H, ꢀCH2 ꢀCH2ꢀCH3), 1.19 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.88
(m, 1H, CHꢀN), 5.92 (d, 1H, NH), 7.58 (d, 2H, H-3% and H-5%), 7.64 (d, 2H, H-2% and H-6%).
0.88 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.16 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (bd, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.85
(m, 1H, CHꢀN), 6.0 (d, 1H, NH), 7.32 (d, 1H, H-5%), 7.40 (s, 1H, H-3%), 7.61 (d, 1H, H-6%).
0.86 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.18 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (bd, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal), 3.85
(m, 1H, CHꢀN), 5.96 (d, 1H, NH), 7.42 (t, 2H, H-3% and H-5%), 7.48 (t, 1H, H-4%), 7.76 (d, 2H, H-2% and H-6%).
0.87 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.19 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (bd, 2H, CH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal), 3.85
(m, 1H, CHꢀN), 5.96 (d, 1H, NH), 7.21 (d, 2H, H-3% and H-5%), 7.63 (d, 2H, H-2% and H-6%).
0.86 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.18 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (bd, 2H, CH2ꢀCH2ꢀCH3), 1–2.1 (m, 9H, cycloal), 3.85
(m, 1H, CHꢀN), 6.06 (d, 1H, NH), 7.92 (d, 2H, H-3% and H-5%), 8.28 (d, 2H, H-2% and H-6%).
0.88 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.18 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3),1–2,2 (m, 9H cycloal.), 3.85
(m, 1H, CHꢀN), 3.86 (s, 3H, 4%-OCH3), 3.90 (s, 6H, 3%- and 5%-OCH3), 6.18 (d, 1H, NH), 7.02 (s, 2H, H-2% and H-6%).
0.85 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.16 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.86
(m, 1H, CHꢀN), 5.58 (d, 1H, NH), 6.34 (d, 1H, CHꢁCHꢀCO), 7.32 (d, 2H, H-3% and H-5%), 7.42 (d, 2H, H-2% and H-6%) 7.56
(d, 1H, CHꢁCHꢀCO).
6d
6e
6f
6g
6h
7a
7b
7b
7c
7d
7e
7f
7g
7h
8
0.85 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.16 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.86
(m, 1H, CHꢀN), 5.58 (d, 1H, NH), 6.34 (d, 1H, CHꢁCHꢀCO), 7.32 (d, 2H, H-3% and H-5%), 7.42 (d, 2H, H-2% and Hꢀ6%) 7.56
(d, 1H, CHꢁCHꢀCO).
0.87 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.19 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.88
(m, 1H, CHꢀN), 5.92 (d, 1H, NH), 6.32 (d, 1H, ꢀCHꢁCHꢀCO), 7.03 (t, 2H, H-3% and H-5%), 7.48 (dd, 2H, H-2% and H-6%),
7.58 (d, 1H, CHꢁCHꢀCO).
0.87 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.19 (m, 2H, ꢀCH2 ꢀCH2ꢀCH3), 1.82 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.88
(m, 1H, CHꢀN), 5.64 (d, 1H, NH), 6.38 (d, 1H, CHꢁCHꢀCO), 7.36 (d, 2H, H-3% and H-5%), 7.44 (d, 2H, H-2% and H-6%), 7.56
(d, 1H, CHꢁCHꢀCO).
0.88 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.16 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (bd, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal.), 3.93
(m, 1H, CHꢀN), 5.96 (d, 1H, NH), 6.42 (d, 1H, CHꢁCHꢀCO), 7.32 (d, 1H, H-5%), 7.40 (s, 1H, H-3%), 7.61 (d, 1H, H-6%), 7.90
(d, 1H, CHꢁCHꢀCO).
0.88 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.18 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (bd, 2H, ꢀCH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal), 3.85
(m, 1H, CHꢀN), 5.96 (d, 1H, NH), 6.43 (d, 1H, CHꢁCHꢀCO), 7.42 (t, 2H, H-3% and H-5%), 7.48 (t, 1H, H-4%), 7.50 (d, 2H,
H-2% and H-6%). 7.63 (d, 1H, CHꢁCHꢀCO).
0.88 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.19 (m, 2H, ꢀCH2ꢀCH2ꢀCH3),1.82 (bd, 2H, CH2ꢀCH2ꢀCH3), 1–2.2 (m, 9H, cycloal), 3.85
(m, 1H, CHꢀN), 5.96 (d, 1H, NH), 6.34 (d, 1H, CHꢁCHꢀCO), 7.18 (d, 2H, H-3%, H-5%), 7.38 (d, 2H, H-2% and H-6%), 7.58
(d, 1H, CHꢁCHꢀCO).
0.88 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.18 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.82 (bd, 2H, CH2ꢀCH2ꢀCH3), 1–2.1 (m, 9H, cycloal), 3.85
(m, 1H, CHꢀN), 6.14 (d, 1H, NH), 6.84 (d, 1H, CHꢁCHꢀCO), 7.64 (d, 2H, Hꢀ2% and H-6%), 8.14 (d, 2H, H-3%, H-5%), 7.80
(d, 1H, CHꢁCHꢀCO).
0.88 (t, 3H, ꢀCH2ꢀCH2ꢀCH3), 1.25 (m, 2H, ꢀCH2ꢀCH2ꢀCH3), 1.12 (bd, 2H, CH2ꢀCH2ꢀCH3), 1–2.3 (m, 9H, cycloal), 3.85
(m, 1H, CHꢀN), 5.25 (d, 1H, NH).
a CDCl3, l (ppm), J (Hz).
ment with iodine vapors. Chromatographic and flash
chromatographic separations were performed on
columns packed with silica gel 60, Merck 70–230 mesh
ASTM and Merck 230–400 mesh ASTM, respectively.
Melting points were determined using a Kofler hot
stage microscope and are uncorrected.
Elemental analyses were performed on a Perkin–
Elmer model 2400. Analytical results were within 9
0.4% of the theoretical values unless otherwise
indicated.
pellets and liquid samples as films.
GC–MS spectra were obtained from a HP5970A
(Hewlett–Packard) apparatus, equipped with a capil-
lary column HP-5 (25 m×0.2 mm×0.11 mm). Pro-
grammed temperature ranged from 100 to 300°C
(10°C/min), the detector temperature was set to 300°C
and the carrier gas was helium at a pressure of 10 psi.
1
The H NMR measurements were performed on a
Bruker AMX 500 MHz spectrometer equipped with a
Bruker X-32 computer, using CDCl3 as solvent and
tetramethylsilane as internal standard. Chemical shifts
are expressed in parts per million downfield from te-
IR spectra were recorded on a Perkin–Elmer model
298 spectrophotometer, including solid samples in KBr