Med Chem Res (2013) 22:3760–3778
3773
1
Table 5 H NMR spectral data for selected compounds
1
Compound
no.
H NMR
4
*
NH
7
2
(under DMSO); 3.70, 3.75 (two s, each 3H, 2OCH
.21 (d, 1H, J = 3.05 Hz, Ar–C –H); 7.77 (d, 1H, J = 16.05 Hz, CH = CH–CO); 12.33 (s, 1H, NH, D
3
); 6.52 (d, 1H, J = 16.05 Hz, CH–CO); 6.90–7.00 (m, 2H, Ar–C3,4–H);
6
2
O-exchangeable)
5
a*
3.71, 3.74, 3.80, 3.81 (four s, 6H, OCH
conformers), 6.90–7.02 (m, 2H, dimethoxyphenyl–C3,4–H); 7.11 (d, 1H, J = 2.3 Hz, dimethoxyphenyl–C
3
cis and trans conformers), 6.75, 7.60 (two d, 1H, J = 16.05 Hz, = CH–CO cis and trans
6
–H); 7.35–7.44 (m,
3
H, phenyl–C3,4,5–H); 7.70 (d, 2H, J = 6.9 Hz, phenyl–C2,6–H), 7.79, 7.87 (two d, 1H, J = 16.05 Hz, CH=CH–CO cis and
trans conformers); 8.03, 8.21 (two s, 1H, CH=N cis and trans conformers) 11.50, 11.68 (two s, 1H, NH, D
and trans conformers)
2
O-exchangeable cis
5
b*
c*
3.80, 3.83, 3.85, 3.87 (four s, 6H, OCH
J = 3.8 Hz, dimethoxyphenyl–C –H); 7.39 (d, 2H, J = 8.4 Hz, p-chlorophenyl–C2,6–H); 7.65 (d, 2H, J = 8.4 Hz, p-
chlorophenyl–C3,5–H), 7.52, 7.57 (two d, 1H, J = 8.4, 16.05 Hz,=CH–CO cis and trans conformers), 7.83, 8.18 (two d, 1H,
J = 16.05 Hz, CH=CH–CO cis and trans conformers); 7.95, 7.98 (two s, 1H, CH=N cis and trans conformers) 9.98, 10.25 (two
3
cis and trans conformers), 6.94–7.04 (m, 2H, dimethoxyphenyl–C3,4–H); 7.20 (d, 1H,
6
s, 1H, NH, D
3.72, 3.75, 3.81, 3.82 (four s, 6H, OCH
J = 3.1 Hz, dimethoxyphenyl–C –H); 7.96 (d, 2H, J = 8.4 Hz, p-nitrophenyl–C2,6–H); 8.26 (d, 2H, J = 8.4 Hz, p-
2
O-exchangeable cis and trans conformers)
5
3
cis and trans conformers), 6.95–7.03 (m, 2H, dimethoxyphenyl–C3,4–H); 7.12 (d, 1H,
6
nitrophenyl–C3,5–H), 6.76, 7.60 (two d, 1H, J = 8.4, 16.05 Hz, =CH–CO cis and trans conformers), 7.80, 7.88 (two d, 1H,
J = 16.05 Hz, CH=CH–CO cis and trans conformers); 8.12, 8.30 (two s, 1H, CH=N cis and trans conformers), 11.78, 11.95
(
two s, 1H, NH, D
2.17 (s, 3H, COCH ); 3.71, 3.74 (two s, each 3H, OCH
J = 9.2 Hz, dimethoxyphenyl–C –H); 7.00 (d, 1H, J = 16.05 Hz, phenyl–CH=CH); 7.07 (s, 1H, oxadiazoline–C
H, J = 3.05 Hz, dimethoxyphenyl–C –H); 7.42 (d, 1H, J = 16.05 Hz, CH=CH); 7.44 (d, 2H, J = 8.4 Hz, p-chlorophenyl–
2,6–H); 7.49 (d, 2H, J = 8.4 Hz, p-chlorophenyl–C3,5–H)
); 3.79, 3.84 (two s, each 3H, OCH ); 6.75 (d, 1H, J = 16.05 Hz, phenyl–CH=CH); 6.85 (d, 1H, J = 9.2 Hz,
–H); 6.90 (dd, 1H, J = 9.2, 3.05 Hz, dimethoxyphenyl–C –H); 7.02 (d, 1H, J = 3.05 Hz,
–H); 7.06 (s, 1H, oxadiazoline–C –H); 7.59 (d, 1H, J = 16.05 Hz, CH=CH); 7.67 (d, 2H, J = 8.4 Hz,
2
O-exchangeable cis and trans conformers)
6
6
7
b*
3
3
); 6.91 (dd, 1H, J = 9.2, 3.05 Hz, dimethoxyphenyl–C
4
–H); 6.96 (d, 1H,
–H); 7.30 (d,
3
5
1
C
6
c**
a*
2.30 (s, 3H, COCH
3
3
dimethoxyphenyl–C
dimethoxyphenyl–C
3
6
4
5
p-nitrophenyl–C2,6–H); 8.26 (d, 2H, J = 8.4 Hz, p-nitrophenyl–C3,5–H)
3.71, 3.79 (two s, each 3H, OCH ); 6.68 (d, 1H, J = 14.5 Hz, =CH–CO); 6.95 (dd, 1H, J = 9.15, 3.05 Hz, dimethoxyphenyl–C
H); 7.00 (d, 1H, J = 9.15 Hz, dimethoxyphenyl–C –H); 7.06 (d, 1H, J = 3.05 Hz, dimethoxyphenyl–C –H); 7.11 (t, 1H,
J = 7.95 Hz, phenyl–C –H); 7.29 (t, 2H, J = 7.95 Hz, phenyl–C3,5–H); 7.38–7.48 (m, 2H, phenyl–C2,6–H); 7.68 (d, 1H,
J = 15.85 Hz, CH=CH–CO); 9.70, 10.12 (two s, 3H, NH, D O-exchangeable)
3.70, 3.78 (two s, each 3H, OCH ); 6.68 (d, 1H, J = 14.5 Hz, =CH–CO); 6.90–7.10 (m, 3H, dimethoxyphenyl–C3,4,6–H); 7.34 (d,
H, J = 8.4 Hz, p-chlorophenyl–C2,6–H); 7.46 (d, 2H, J = 8.4 Hz, p-chlorophenyl–C3,5–H); 7.69 (d, 1H, J = 16.05 Hz,
CH=CH–CO); 9.77, 10.12 (two s, 3H, NH, D O-exchangeable)
3.71, 3.79 (two s, 12H, 4OCH ); 6.80 (d, 2H, J = 16.05 Hz, CH–CO); 6.94 (dd, 2H, J = 9.15, 3.05 Hz, Ar–C
J = 9.15 Hz, Ar–C –H); 7.08 (d, 2H, J = 3.05 Hz, Ar–C –H); 7.68 (d, 2H, J = 16.05 Hz, CH=CH–CO); 10.43 (s, 2H, 2NH,
O-exchangeable)
3.60, 3.63 (two s, each 3H, OCH
dimethoxyphenyl–C –H); 6.88 (d, 1H, J = 9.2 Hz, dimethoxyphenyl–C
H); 7.36 (d, 1H, J = 16.8 Hz, CH=CH); 7.41 (d, 2H, J = 6.9 Hz, phenyl–C2,6–H); 7.51–7.61 (m, 3H, phenyl–C3,4,5–H); 14.01
s, 1H, SH, D O-exchangeable)
2.38 (s, 3H, C –CH ); 3.62, 3.64 (two s, each 3H, OCH
.05 Hz, dimethoxyphenyl–C –H); 6.89 (d, 1H, J = 9.15 Hz, dimethoxyphenyl–C
dimethoxyphenyl–C –H); 7.27 (d, 2H, J = 8.4 Hz, p-tolyl–C3,5–H); 7.36 (d, 1H, J = 16.8 Hz, CH=CH); 7.37 (d, 2H,
J = 8.4 Hz, p-tolyl–C2,6–H); 13.96 (s, 1H, SH, D O-exchangeable)
2.56 (s, 3H, S–CH ); 3.62, 3.64 (two s, each 3H, OCH ); 6.71 (d, 1H, J = 16.05 Hz, phenyl–CH=CH); 6.82 (dd, 1H, J = 9.2,
.05 Hz, dimethoxyphenyl–C –H); 6.88 (d, 1H, J = 9.2 Hz, dimethoxyphenyl–C –H); 6.99 (d, 1H, J = 3.05 Hz,
dimethoxyphenyl–C –H); 7.42–7.47 (m, 2H, phenyl–C –H); 7.48 (d, 1H, J = 16.05 Hz, CH=CH); 7.57–7.63 (m, 3H, phenyl–
3
4
–
3
6
4
2
7
8
9
b*
3
2
2
*
3
4
–H); 7.00 (d, 2H,
3
6
D
2
a*
3
); 6.59 (d, 1H, J = 16.8 Hz, phenyl–CH=CH); 6.85 (dd, 1H, J = 9.2, 3.05 Hz,
6
–H); 6.97 (d, 1H, J = 3.05 Hz, dimethoxyphenyl–C –
4
3
(
2
9
1
1
1
c*
H
6 4
3
3
); 6.57 (d, 1H, J = 16.8 Hz, phenyl–CH=CH); 6.86 (dd, 1H, J = 9.15,
–H); 6.98 (d, 1H, J = 3.05 Hz,
3
4
3
6
2
0a*
0b*
0e*
3
3
3
4
3
6
2 6
,
3
C ,4,5–H)
1.26 (t, 3H, J = 7.2 Hz, SCH
J = 16.05 Hz, phenyl–CH=CH); 6.84 (dd, 1H, J = 9.2, 3.05 Hz, dimethoxyphenyl–C
dimethoxyphenyl–C –H); 6.99 (d, 1H, J = 3.05 Hz, dimethoxyphenyl–C –H); 7.41–7.45 (m, 2H, phenyl–C
J = 16.05 Hz, CH=CH); 7.58–7.63 (m, 3H, phenyl–C
1.25 (t, 3H, J = 7.2 Hz, SCH CH ); 3.06 (q, 2H, J = 7.2 Hz, SCH
phenyl–CH=CH); 6.85 (dd, 1H, J = 9.2, 3.05 Hz, dimethoxyphenyl–C
.06 (d, 1H, J = 3.05 Hz, dimethoxyphenyl–C –H); 7.49 (d, 1H, J = 16.05 Hz, CH=CH); 7.50 (d, 2H, J = 8.4 Hz, p-
chlorophenyl–C –H); 7.68 (d, 2H, J = 8.4 Hz, p-chlorophenyl–C –H)
2
CH
3
); 3.07 (q, 2H, J = 7.2 Hz, SCH
2
CH
3
); 3.63, 3.64 (two s, each 3H, OCH
–H); 6.90 (d, 1H, J = 9.2 Hz,
–H); 7.49 (d, 1H,
3
); 6.72 (d, 1H,
4
3
6
2 6
,
3
,4,5–H)
2
3
2
CH
3
); 3.66 (s, 6H, OCH
–H); 6.89 (d, 1H, J = 9.2 Hz, dimethoxyphenyl–C
3
); 6.72 (d, 1H, J = 16.05 Hz,
4
3
–H);
7
6
,
2 6
3 5
,
123