Med Chem Res
?
1
54.3 (C ), 142.1 (C ), (=CH), 131.4–119.9 (aromatic and
1
(OCH ), 48.4 (C ) (–CH –). MS (m/z): 483 (M ). Anal.
3 13 2
6
6
benzothiazole) (C7–12, C17–21), 115.4 (C ), 111.7 (C ),
5
calcd for C H O N S : C 52.27, H 2.92, N 11.61; found
21 14 4 4 3
22
?
9.4 (C ), (–CH –). MS (m/z): 471 (M ). Anal. calcd for
4
C 52.23, H 2.88, N 11.57.
1
3
2
C H O N S F: C 51.05, H 2.36, N 11.91; found C 51.03,
20 11 3 4 3
(
E)-2-(5-(4-(dimethylamino)benzylidene)-2,4-dioxothiazolid-
H 2.33, N 11.88.
in-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl) acetamide
25 Reddish brown solid, m.p. 260–261 °C, yield, 59 %;
IR (KBr) m cm : 3420 (CONH), 2947 and 2776 (–CH2–
(
E)-2-(5-(3-bromobenzylidene)-2,4-dioxothiazolidin-3-yl)-N-
6-thiocyanatobenzo[d]thiazol-2-yl)acetamide 22 Yellow-
-
1
(
ish brown solid, m.p. 261–263 °C, yield, 65 %; IR (KBr) m
cm : 3424 (CONH), 2945 and 2774 (–CH2– methylene),
methylene), 2872 (=CH), 2164 (–SC:N–), 1715 (CONH,
amide-I), 1523 (amide-II), 1268 (amide-III), 1756 and
-
1
1
2
1
8
872 (=CH), 2158 (–SC:N–), 1714 (CONH, amide-I),
526 (amide-II), 1265 (amide-III), 1759 and 1643 (C=O),
1638 (C=O) and 817 (C–S–C). H NMR (DMSO-d ) d
6
(ppm): 10.67 (s, 1H, CONH), 8.95 (s, 1H, =CH), 7.82–6.80
1
15 (C–S–C), 627 (C–Br str.). H NMR (DMSO-d ) d
(m, 7H, aromatic and benzothiazole), 4.34 (s, 2H, –CH –),
2
6
1
3
(
(
ppm): 10.65 (s, 1H, CONH), 7.98 (s, 1H, =CH), 7.78–7.25
2.96 (s, 6H, –N(CH ) ). C NMR (100 MHz, DMSO-d6)
3 2
m, 7H, aromatic and benzothiazole), 4.43 (s, 2H, –CH –).
2
d(ppm): 174.6 (C ), 170.0 (C ), 167.9 (C ), (–CONH–),
15
2
14
1
3
C NMR (100 MHz, DMSO-d ) d(ppm): 175.0 (C ),
165.8 (C ), (CO), 155.1 (C ), 150.1 (C ), 142.3 (C ),
4 16 10 6
6
15
1
70.1 (C ), 168.7 (C ), (–CONH–), 165.6 (C ), (CO),
2
(=CH), 130.0–116.8 (aromatic and benzothiazole)
(C7–9,11,12, C17–21), 115.1 (C ), 111.2 (C ), 49.1 (C )
14
4
1
54.9 (C ), 142.5 (C ), (=CH), 135.4–122.0 (aromatic and
6
1
6
5
22
13
?
benzothiazole) (C7–12, C17–21), 115.5 (C ), 111.0 (C ),
5
(–CH –), 40.4 (C
2
) (N(CH ) ). MS (m/z): 496 (M ).
23,24 3 2
22
?
9.7 (C ), (–CH –). MS (m/z): 531 (M ), 533 (M ? 2).
?
4
Anal. calcd for C H O N S : C 53.32, H 3.46, N 14.13;
22 17 3 5 3
1
3
2
Anal. calcd for C H O N S Br: C 45.20, H 2.09, N
20 11 3 4 3
found C 53.28, H 3.43, N 14.11.
1
0.54; found C 45.18, H 2.07, N 10.51.
(E)-2-(5-(4-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl)-N-
(
E)-2-(5-(4-methylbenzylidene)-2,4-dioxothiazolidin-3-yl)-N-
6-thiocyanatobenzo[d]thiazol-2-yl)acetamide 23 Brown
(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide
26 Brown
1
-
(
solid, m.p. 236–238 °C, yield, 82 %; IR (KBr) m cm
3516 (–OH), 3416 (CONH), 2947 and 2764 (–CH2–
:
-
1
solid, m.p. 231–233 °C, yield, 75 %; IR (KBr) m cm
3
:
421 (CONH), 2944 and 2770 (–CH2– methylene), 2876
methylene), 2873 (=CH), 2166 (–SC:N–), 1715 (CONH,
amide-I), 1521 (amide-II), 1267 (amide-III), 1756 and
(
(
(
=CH), 2160 (–SC:N–), 1716 (CONH, amide-I), 1522
amide-II), 1270 (amide-III), 1755 and 1636 (C=O), 814
1
1634 (C=O) and 817 (C–S–C). H NMR (DMSO-d ) d
6
1
C–S–C). H NMR (DMSO-d ) d (ppm): 11.21 (s, 1H,
(ppm): 10.59 (s, 1H, CONH), 7.98 (s, 1H, =CH), 7.81–6.70
6
CONH), 7.95 (s, 1H, =CH), 7.72–7.04 (m, 7H, aromatic
(m, 7H, aromatic and benzothiazole), 4.27 (s, 2H, –CH –),
2
1
3
and benzothiazole), 4.18 (s, 2H, –CH –), 2.32 (s, 3H,
2
5.21 (s, 1H, –OH). C NMR (100 MHz, DMSO-d6)
d(ppm): 174.9 (C ), 170.3 (C ), 167.8 (C ), (–CONH–),
1
3
–
CH3). C NMR (100 MHz, DMSO-d ) d(ppm): 175.1
6
15
2
14
(
(
C ), 170.1 (C ), 168.0 (C ), (–CONH–), 165.5 (C ),
2
165.8 (C ), (CO), 158.3 (C ), 154.6 (C ), 142.4 (C ),
4 10 16 6
15
14
4
CO), 154.9 (C ), 142.1 (C ), (=CH), 136.9–121.9 (aro-
1
(=CH), 131.4–116.1 (aromatic and benzothiazole)
(C7–9,11,12, C17–21), 114.9 (C ), 111.6 (C ), 49.1 (C )
6
6
matic and benzothiazole) (C7–12, C17–21), 115.2 (C ), 111.4
5
5
22
13
?
(
C ), 49.1 (C ), (–CH –), 20.8 (C ), (CH ). MS (m/z):
13
(–CH –). MS (m/z): 469 (M ). Anal. calcd for C H O
2 20 12 4
22
2
23
3
?
67 (M ). Anal. calcd for C H O N S : C 54.06, H 3.02,
4
N S : C 51.27, H 2.58, N 11.96; found C 51.25, H 2.55, N
4 3
2
1
14
3
4
3
N 12.01; found C 54.04, H 3.00, N 11.98.
E)-2-(5-(4-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)-N-
6-thiocyanatobenzo[d] thiazol-2-yl)acetamide 24 Dark
brown solid, m.p. 248–250 °C, yield, 61 %; IR (KBr) m
11.93.
(
(E)-2-(5-(4-hydroxy-3-methoxybenzylidene)-2,4-dioxoth-
iazolidin-3-yl)-N-(6-thiocyanato benzo[d]thiazol-2-yl)
acetamide 27 Brown solid, m.p. 271–273 °C, yield,
(
-
1
-1
cm : 3428 (CONH), 2934 and 2763 (–CH2– methylene),
66 %; IR (KBr) m cm : 3511 (–OH), 3428 (CONH), 2947
2
1
875 (=CH), 2154 (–SC:N–), 1707 (CONH, amide-I),
516 (amide-II), 1256 (amide-III), 1761 and 1633 (C=O)
and 2776 (–CH2– methylene), 2874 (=CH), 2166 (–SC:
N–), 1714 (CONH, amide-I), 1524 (amide-II), 1276
1
(amide-III), 1756 and 1637 (C=O) and 809 (C–S–C). H
1
and 805 (C–S–C). H NMR (DMSO-d ) d (ppm): 10.58 (s,
6
1
H, CONH), 7.94 (s, 1H, =CH), 7.82–6.82 (m, 7H, aro-
NMR (DMSO-d ) d (ppm): 10.66 (s, 1H, CONH), 7.97 (s,
6
matic and benzothiazole), 4.39 (s, 2H, –CH –), 3.80 (s, 3H,
2
1H, =CH), 7.78–6.92 (m, 6H, aromatic and benzothiazole),
1
3
–
OCH3). C NMR (100 MHz, DMSO-d ) d(ppm): 175.1
4.28 (s, 2H, –CH –), 5.19 (s, 1H, –OH), 3.78 (s, 3H,
2
6
1
3
(
C ), 170.1 (C ), 168.5 (C ), (–CONH–), 165.6 (C ),
2
–OCH3). C NMR (100 MHz, DMSO-d ) d(ppm): 174.6
15
14
4
6
(
CO), 160.3 (C ), 155.0 (C ), 142.1 (C ), (=CH),
16
(C ), 170.3 (C ), 167.8 (C ), (–CONH–), 165.2 (C ),
4
1
0
6
15
2
14
1
30.4–116.5 (aromatic and benzothiazole) (C7–9,11,12
,
(CO), 155.6 (C ), 149.9 (C ), 148.3 (C ), 141.7 (C ),
16 11 10 6
C17–21), 115.4 (C ), 113.9 (C ), 111.5 (C ), 55.3 (C )
22
(=CH), 127.8–116.2 (aromatic and benzothiazole) (C7–9,12,
5
9,11
23
123