A. Kamal et al. / Bioorg. Med. Chem. 20 (2012) 3480–3492
3489
165 °C; 1H NMR (300 MHz, CDCl3): d 10.59 (bs, 1H), 7.76–7.81 (m,
5.10. (E)-2-(2-Methoxy-5-(3-oxo-3-(3,4,5-
1H), 7.71 (d, 1H, J = 15.1 Hz), 7.65–7.69 (m, 2H), 7.46 (d, 1H,
J = 2.0 Hz), 7.37–7.41 (dd, 1H, J = 8.5, 2.0 Hz), 7.25 (s, 2H), 7.21 (d,
1H, J = 15.1 Hz), 6.86 (d, 1H, J = 8.3 Hz), 4.83 (s, 2H), 4.07 (s, 3H),
3.95 (s, 6H), 3.93 (s, 3H); 13C NMR (75 MHz, CDCl3): d 187.8,
167.2, 157.8, 152.3, 151.2, 147.5, 147.3, 143.7, 141.7, 133.2, 131.1,
129.8, 127.4, 124.6, 124.1, 123.5, 119.7, 119.1, 113.6, 112.2, 105.9,
67.0, 60.1, 56.1, 55.6; MS-ESI(+): m/z 570 [M+H]+; HRMS-ESI(+)
for C28H26ClN2O7S Calcd 570.0253, Found 570.0239 [M+H]+.
trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-trifl
uoromethylbenzo[d]thiazol-2-yl)acetamide (9g)
This compound was prepared according to the method de-
scribed for compound 9a by employing compound 8 (402 mg,
1 mmol), EDCI (210 mg, 1.1 mmol), HOBt (13.5 mg, 0.1 mmol)
and 2-amino-6-trifluoromethylbenzothiazole (218 mg, 1 mmol)
to obtain the pure product 9g as yellow solid. (490 mg, 81% yield);
mp 167–169 °C; 1H NMR (300 MHz, CDCl3): d 10.74 (bs, 1H), 8.11
(s, 1H), 7.87 (d, 1H, J = 8.3 Hz), 7.64–7.74 (m, 2H), 7.28–7.40 (m,
3H), 7.22 (s, 2H), 6.99 (d, 1H, J = 8.3 Hz), 4.84 (s, 2H), 4.09 (s, 3H),
3.95 (s, 6H), 3.91 (s, 3H); 13C NMR (75 MHz, DMSO-d6): d 187.7,
167.9, 158.7, 152.7, 151.3, 147.2, 144, 143.8, 141.7, 133.1, 132.6,
128.5, 127.4, 124.2, 121.5, 119.8, 118.3, 114.9, 113.7, 112.2,
105.9, 67.0, 60.0, 56.0, 55.7; MS-ESI(+): m/z 603 [M+H]+; HRMS-
ESI(+) for C29H26F3N2O7S Calcd 603.5776, Found 603.5761 [M+H]+.
5.7. (E)-2-(2-Methoxy-5-(3-oxo-3-(3,4,5-
trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-nitro
benzo[d]thiazol-2-yl)acetamide (9d)
This compound was prepared according to the method de-
scribed for compound 9a by employing compound 8 (402 mg,
1 mmol), EDCI (210 mg, 1.1 mmol), HOBt (13.5 mg, 0.1 mmol) and
2-amino-6-nitrobenzothiazole (195 mg, 1 mmol) to obtain the pure
product 9d as yellow solid. (482 mg, 83% yield); mp 169–170 °C; 1H
NMR (200 MHz, CDCl3): d 10.98 (bs, 1H), 8.77 (d, 1H, J = 2.1 Hz),
8.31–8.38 (dd, 1H, J = 8.3, 2.1 Hz), 7.79 (d, 1H, J = 15.6 Hz), 7.72 (d,
1H, J = 8.3 Hz), 7.28–7.34 (m, 2H), 7.25 (d, 1H, J = 15.6 Hz), 7.23 (s,
2H), 6.95 (d, 1H, J = 8.3 Hz), 4.83 (s, 2H), 4.01 (s, 3H), 3.92 (s, 6H),
3.9 (s, 3H); 13C NMR (75 MHz, CDCl3):d 187.8, 168.6, 160.8, 152.8,
151.3, 147.7, 147.2, 143.9, 141.7, 133.2, 131.1, 129.9, 127.7, 126.2,
124.2, 121.5, 119.9, 119.2, 113.5, 112.2, 105.9, 67.1, 60.2, 56.1,
55.3; MS-ESI(+): m/z 580 [M+H]+; HRMS-ESI(+) for C28H26N3O9S
Calcd 580.5667, Found 580.5661 [M+H]+.
5.11. (E)-2-(2-Methoxy-5-(3-oxo-3-(3,4,5-
trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-
methylbenzo[d]thiazol-2-yl)acetamide (9h)
This compound was prepared according to the method de-
scribed for compound 9a by employing compound 8 (402 mg,
1 mmol), EDCI (210 mg, 1.1 mmol), HOBt (13.5 mg, 0.1 mmol)
and 2-amino-6-methylbenzothiazole (164 mg, 1 mmol) to obtain
the pure product 9 h as yellow solid. (450 mg, 82% yield); mp
162–164 °C; 1H NMR (300 MHz, CDCl3):
d
7.76 (d, 1H,
J = 15.6 Hz), 7.70 (d, 1H, J = 8.3 Hz), 7.63 (s, 1H), 7.31–7.43 (m,
2H), 7.23–7.30 (m, 4H), 7.01 (d, 1H, J = 8.4 Hz), 4.84 (s, 2H), 4.04
(s, 3H), 3.96 (s, 3H), 3.94 (s, 3H), 2.48 (s, 3H); 13C NMR (75 MHz,
CDCl3): d 187.7, 167.5, 153.1, 151.8, 147.3, 143.7, 141.6, 133.1,
131.4, 127.5, 126.1, 124.3, 123.6, 121.7, 120.5, 119.9, 113.2,
112.2, 105.8, 67.2, 60.2, 56.7, 55.8, 28.3; MS-ESI(+): m/z 549
[M+H]+; HRMS-ESI(+) for C29H29N2O7S Calcd 549.1695, Found
549.1696 [M+H]+.
5.8. (E)-2-(2-Methoxy-5-(3-oxo-3-(3,4,5-
trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-meth
oxybenzo[d]thiazol-2-yl)acetamide (9e)
This compound was prepared according to the method de-
scribed for compound 9a by employing compound 8 (402 mg,
1 mmol), EDCI (210 mg, 1.1 mmol), HOBt (13.5 mg, 0.1 mmol)
and 2-amino-6-methoxybenzothiazole (180 mg, 1 mmol) to obtain
the pure product 9e as yellow solid. (475 mg, 84% yield); mp 166–
167 °C; 1H NMR (300 MHz, CDCl3): d 10.62 (bs, 1H), 7.75 (d, 1H,
J = 15.6 Hz), 7.71 (d, 1H, J = 8.0 Hz), 7.34–7.4 (m, 2H), 7.28–7.34
(m, 2H), 7.23 (d, 1H, J = 15.6 Hz), 7.22 (s, 2H), 6.89 (d, 1H,
J = 8.3 Hz), 4.82 (s, 2H), 4.02 (s, 3H), 3.96 (s, 6H), 3.95 (s, 3H),
3.88 (s, 3H); 13C NMR (75 MHz, CDCl3): d 187.7, 167.3, 156.1,
155.1, 152.8, 151.3, 147.3, 143.9, 142.4, 141.6, 133.1, 132.7,
127.4, 124.2, 121.2, 119.8, 114.9, 113.5, 112.1, 105.9, 104.6, 67.0,
60.1, 56.0, 55.7, 55.5; MS-ESI(+): m/z 565 [M+H]+; HRMS-ESI(+)
for C29H29N2O8S Calcd 565.6061, Found 565.6054 [M+H]+.
5.12. (E)-2-(2-Methoxy-5-(3-oxo-3-(3,4,5-
trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-
ethoxybenzo[d]thiazol-2-yl)acetamide (9i)
This compound was prepared according to the method described
for compound 9a by employing compound 8 (402 mg, 1 mmol),
EDCI (210 mg, 1.1 mmol), HOBt (13.5 mg, 0.1 mmol) and 2-amino-
6-ethoxybenzothiazole (194 mg, 1 mmol) to obtain the pure prod-
uct 9i as yellow solid. (460 mg, 79% yield); mp 165–167 °C; 1H
NMR (200 MHz, CDCl3): d 7.75 (d, 1H, J = 15.8 Hz), 7.70 (d, 1H,
J = 9.0 Hz), 7.36–7.41 (m, 2H), 7.29–7.34 (m, 2H), 7.25–7.28 (m,
3H), 7.01 (d, 1H, J = 8.3 Hz), 4.84 (s, 2H), 4.06–4.15 (q, 2H), 4.04 (s,
3H), 3.96 (s, 6H), 3.95 (s, 3H), 1.46 (t, 3H); 13C NMR (75 MHz, CDCl3):
d 187.4, 166.4, 156.4, 155.3, 152.9, 151.8, 147.2, 143.3, 142.5, 141.7,
133.3, 132.7, 127.7, 124.1, 121.5, 119.9, 115.0, 113.4, 112.3, 105.4,
104.7, 67.1, 60.7, 56.3, 55.9, 55.1, 31.5; MS-ESI(+): m/z 579
[M+H]+; HRMS-ESI(+) for C30H31N2O8S Calcd 579.1801, Found
579.1781 [M+H]+.
5.9. (E)-2-(2-Methoxy-5-(3-oxo-3-(3,4,5-
trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-
trifluoromethoxybenzo[d]thiazol-2-yl) acetamide (9f)
This compound was prepared according to the method de-
scribed for compound 9a by employing compound 8 (402 mg,
1 mmol), EDCI (210 mg, 1.1 mmol), HOBt (13.5 mg, 0.1 mmol)
and 2-amino-6-trifluoromethoxybenzothiazole (234 mg, 1 mmol)
to obtain the pure product 9f as yellow solid. (502 mg, 81% yield);
mp 168–170 °C; 1H NMR (300 MHz, CDCl3): d 10.62 (bs, 1H), 7.77
(d, 1H, J = 9.0 Hz), 7.66–7.73 (m, 2H), 7.27–7.39 (m, 3H), 7.24 (d,
1H, J = 15.1 Hz), 7.22 (s, 2H), 6.98 (d, 1H, J = 8.3 Hz), 4.83 (s, 2H),
4.07 (s, 3H), 3.95 (s, 6H), 3.91 (s, 3H); 13C NMR (75 MHz, DMSO-
d6): d 187.8, 168.2, 160.5, 152.7, 151.3, 151.1, 147.2, 143.9,
141.69, 133.1, 131.9, 127.4, 126.2, 124.2, 122.9, 122.6, 121.0,
119.8, 113.7, 112.2, 105.9, 67.0, 60.1, 56.0, 55.7; MS-ESI(+): m/z
619 [M+H]+; HRMS-ESI(+) for C29H26F3N2O8S calcd 619.5724,
found 619.5710 [M+H]+.
5.13. (E)-2-(2-Methoxy-5-(3-oxo-3-(3,4,5-
trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(4-
methylbenzo[d]thiazol-2-yl)acetamide (9j)
This compound was prepared according to the method de-
scribed for compound 9a by employing compound 8 (402 mg,
1 mmol), EDCI (210 mg, 1.1 mmol), HOBt (13.5 mg, 0.1 mmol)
and 2-amino-4-methylbenzothiazole (164 mg, 1 mmol) to obtain
the pure product 9j as yellow solid. (430 mg, 78% yield); mp
163–165 °C; 1H NMR (200 MHz, CDCl3): d 10.71 (br s, 1H), 7.76