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3.90 (s, 9H), 4.23 (t, J=8.0 Hz, 2H), 7.11 (s, 2H), 7.40 (s, 1H), 7.65–
7.72 (m, 3H), 7.90 (d, J=7.2 Hz, 2H), 9.72 (s, 1H), 9.81 ppm (s, 1H);
13C NMR (100 MHz, [D6]DMSO): d=38.3, 49.2, 56.4, 61.2 (2C), 123.9,
124.4, 125.3 (2C), 126.6, 127.2 (2C), 127.8, 132.7, 133.9, 134.5,
138.6, 144.3, 145.6, 164.6, 168.5, 172.4, 176.7 ppm; MS (ES, 70 eV):
m/z 502 [M+H]+; elemental analysis: calcd (%) for C23H23N3O6S2: C
55.08, H 4.62, N 8.38; found: C 55.14, H 4.72, N 8.40.
(Z)-N’-(3-(5-(4-Nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-
propanoyl)-1-naphthohydrazide (14): Yield: 81%; mp: 263–2648C;
1H NMR (400 MHz, [D6]DMSO): d=2.50 (t, J=8.0 Hz, 2H), 4.21 (t,
J=7.6 Hz, 2H), 7.92–7.72 (m, 10H), 8.10 (d, J=10.0 Hz, 2H),
9.70 ppm (d, J=12.0 Hz, 2H); 13C NMR (100 MHz, [D6]DMSO): d=
36.9, 46.3, 121.2, 121.6, 123.4, 124.2, 124.8, 125.3, 125.9, 126.4,
126.8, 133.4, 134.6, 135.4, 136.7, 137.7, 138.8, 143.3, 144.3, 145.8,
164.6, 166.9, 172.8, 177.3 ppm; MS (ES, 70 eV): m/z 507 [M+H]+;
elemental analysis: calcd (%) for C24H18N4O5S2: C 56.91, H 3.58, N
11.06; found: C 56.97, H 3.62, N 11.16.
(Z)-N’-(3-(4-Oxo-2-thioxo-5-(3,4,5-trimethoxybenzylidene)thiazo-
lidin-3-yl)propanoyl)isonicotinohydrazide (9): Yield: 92%; mp:
196–1988C; 1H NMR (400 MHz, [D6]DMSO): d=2.49 (t, J=7.6 Hz,
2H), 3.93 (s, 9H), 4.32 (t, J=8.0 Hz, 2H), 7.23 (s, 2H), 7.60 (s, 1H),
7.90 (d, J=7.8 Hz, 2H), 8.40 (d, J=8.0 Hz, 2H), 9.61 (s, 1H),
9.72 ppm (s, 1H); 13C NMR (100 MHz, [D6]DMSO): d=39.4, 48.6,
57.4, 59.8 (2C), 123.4, 124.1, 124.9 (2C), 125.1, 126.2, 126.6, 132.3,
133.1, 133.4, 137.4, 143.2, 144.5, 164.3, 169.4, 174.6, 178.7 ppm; MS
(ES, 70 eV): m/z 503 [M+H]+; elemental analysis: calcd (%) for
C22H22N4O6S2: C 52.58, H 4.41, N 11.15; found: C 52.64, H 4.52, N
11.23.
(Z)-N’-(3-(5-(4-Nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-
propanoyl)nicotinohydrazide (15): Yield: 72%; mp: 264–2658C;
1H NMR (400 MHz, CDCl3): d=2.41 (t, J=8.4 Hz, 2H), 4.30 (t, J=
8.4 Hz, 2H), 8.01–7.81 (m, 6H), 8.13 (d, J=9.6 Hz, 2H), 8.70 (s, 1H),
10.21 ppm (d, J=11.6 Hz, 2H); 13C NMR (100 MHz, CDCl3): d=36.5,
47.4, 120.1, 121.9, 124.5, 125.8, 126.4, 127.4, 134.7, 135.4, 136.6,
138.9, 143.3, 145.3, 145.9, 163.6, 165.3, 176.6, 178.7 ppm:; MS (ES,
70 eV): m/z 458 [M+H]+; elemental analysis: calcd (%) for
C19H15N5O5S2: C 49.88, H 3.30, N 15.31; found: C 49.90, H 3.36, N
15.37.
(Z)-N’-(3-(4-Oxo-2-thioxo-5-(3,4,5-trimethoxybenzylidene)thiazo-
lidin-3-yl)propanoyl)-1-naphthohydrazide (10): Yield: 75%; mp:
238–2408C; 1H NMR (400 MHz, CDCl3): d=2.36 (t, J=8.4 Hz, 2H),
3.79 (s, 9H), 4.27 (t, J=8.0 Hz, 2H), 7.19 (s, 2H), 7.65–7.80 (m, 3H),
8.13–8.85 (m, 5H), 10.20 ppm (brs, 2H); 13C NMR (100 MHz, CDCl3):
d=37.9, 49.6, 57.8 (3C), 121.4, 123.1, 124.3 (2C), 125.4, 126.0,
126.6, 127.2, 127.6, 128.3, 129.5, 132.1, 132.7, 133.0, 133.4, 138.2,
141.2, 143.6, 166.3, 171.7, 172.6, 180.7 ppm; MS (ES, 70 eV): m/z
552 [M+H]+; elemental analysis: calcd (%) for C27H25N3O6S2: C
58.79, H 4.57, N 7.62; found: C 58.84, H 4.62, N 7.73.
(Z)-N’-(3-(5-(4-(Benzyloxy)benzylidene)-4-oxo-2-thioxothiazoli-
din-3-yl)propanoyl)benzohydrazide (16): Yield: 70%; mp: 223–
2248C; 1H NMR (400 MHz, [D6]DMSO): d=2.46 (t, J=7.6 Hz, 2H),
4.21 (t, J=8.0 Hz, 2H), 5.20 (s, 2H), 7.20–7.62 (m, 13H), 7.90 (d, J=
9.2 Hz, 2H), 9.72 ppm (d, J=12.4 Hz, 2H); 13C NMR (100 MHz,
[D6]DMSO): d=36.5, 47.4, 72.9, 121.2 (2C), 124.2 (2C), 125.8 (2C),
126.2 (2C), 127.6, 134.7 (2C), 135.4, 136.0, 136.6, 137.0, 138.9,
141.4, 143.8, 144.3, 145.4, 166.9, 168.3, 179.6, 182.7 ppm; MS (ES,
70 eV): m/z 518 [M+H]+; elemental analysis: calcd (%) for
C27H23N3O4S2: C 62.65, H 4.48, N 8.12; found: C 62.70, H 4.56, N
8.16.
(Z)-N’-(3-(4-Oxo-2-thioxo-5-(3,4,5-trimethoxybenzylidene)thiazo-
lidin-3-yl)propanoyl)nicotinohydrazide (11): Yield: 84%; mp: 234–
2368C; 1H NMR (400 MHz, [D6]DMSO): d=2.34 (t, J=8.4 Hz, 2H),
3.87 (s, 9H), 4.19 (t, J=7.6 Hz, 2H), 7.21 (s, 2H), 7.54 (s, 1H), 7.60 (t,
J=8.8 Hz, 1H), 8.10 (s, 1H), 8.64 (s, 1H), 8.71 (s, 1H), 9.61 ppm (d,
J=11.2 Hz, 2H); 13C NMR (100 MHz, [D6]DMSO): d=40.0, 49.3, 56.7,
58.3 (2C), 121.9, 123.6, 124.2 (2C), 124.9, 125.6, 126.1, 132.5, 132.9,
133.9, 138.6, 142.5, 144.8, 163.9, 169.1, 174.2, 177.9 ppm; MS (ES,
70 eV): m/z 503 [M+H]+; elemental analysis: calcd (%) for
C22H22N4O6S2: C 52.58, H 4.41, N 11.15; found: C 52.62, H 448, N
11.21.
(Z)-N’-(3-(5-(4-(Benzyloxy)benzylidene)-4-oxo-2-thioxothiazoli-
din-3-yl)propanoyl)isonicotinohydrazide (17): Yield: 79%; mp:
233–2348C; 1H NMR (400 MHz, CDCl3): d=2.38 (t, J=7.6 Hz, 2H),
4.12 (t, J=8.0 Hz, 2H), 5.11 (s, 2H), 7.18–7.35 (m, 7H), 7.63–7.72 (m,
3H), 7.92 (d, J=7.6 Hz, 2H), 8.31 (d, J=7.2 Hz, 2H), 9.93 ppm (d,
J=12.4 Hz, 2H); 13C NMR (100 MHz, [D6]DMSO): d=180.7, 178.4,
166.3, 162.9, 143.5, 142.3, 142.0, 141.6, 139.5, 138.3, 136.9, 136.4,
135.6, 134.4 (2C), 127.2 (2C), 125.9 (2C), 125.2, 124.7 (2C), 123.2,
72.9, 47.4, 36.5 ppm; MS (ES, 70 eV): m/z 519 [M+H]+; elemental
analysis: calcd (%) for C26H22N4O4S2: C 60.21, H 4.28, N 10.80;
found: C 60.26, H 4.36, N 10.92.
(Z)-N’-(3-(5-(4-Nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-
propanoyl)benzohydrazide (12): Yield: 69%; mp: 248–2498C;
1H NMR (400 MHz, [D6]DMSO): d=2.54 (t, J=8.8 Hz, 2H), 4.12 (t,
J=8.4 Hz, 2H), 7.63–7.83 (m, 7H), 7.92 (s, 1H), 8.31 (d, J=9.6 Hz,
2H), 9.60 ppm (d, J=11.6 Hz, 2H); 13C NMR (100 MHz, [D6]DMSO):
d=38.1, 46.9, 120.1, 120.6, 121.9 (2C), 125.4, 126.1, 126.6, 133.9,
134.6, 135.4, 139.6, 141.6, 143.0, 143.5, 163.4, 168.5, 173.2,
174.9 ppm; MS (ES, 70 eV): m/z 457 [M+H]+; elemental analysis:
calcd (%) for C20H16N4O5S2: C 52.62, H 3.53, N 12.27; found: C 52.72,
H 3.59, N 12.31.
(Z)-N’-(3-(5-(4-(Benzyloxy)benzylidene)-4-oxo-2-thioxothiazoli-
din-3-yl)propanoyl)-1-naphthohydrazide (18): Yield: 90%; mp:
240–2428C; 1H NMR (400 MHz, [D6]DMSO): d=2.43 (t, J=8.4 Hz,
2H), 4.21 (t, J=8.8 Hz, 2H), 5.12 (s, 2H), 7.36–7.20 (m, 5H), 7.92–
7.62 (m, 8H), 8.44–8.31 (m, 4H), 10.17 ppm (d, J=12.8 Hz, 2H);
13C NMR (100 MHz, [D6]DMSO): d=38.3, 49.4, 69.6, 123.2, 124.7
(2C), 125.2, 125.9 (2C), 126.4, 127.5, 128.2 (2C), 129.4, 132.5 (2C),
133.3 (2C), 135.6, 136.2, 136.9, 139.3, 140.7, 141.3, 141.7, 142.1,
143.3, 162.5, 164.3, 177.4, 179.7 ppm; MS (ES, 70 eV): m/z 568 [M+
H]+; elemental analysis: calcd (%) for C31H25N3O4S2: C 65.59, H 4.44,
N 7.40; found: C 65.66, H 4.46, N 7.42.
(Z)-N’-(3-(5-(4-Nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-
propanoyl)isonicotinohydrazide (13): Yield: 72%; mp: 229–2318C;
1H NMR (400 MHz, [D6]DMSO): d=2.61 (t, J=8.4 Hz, 2H), 4.23 (t,
J=7.6 Hz, 2H), 7.63–7.72 (m, 4H), 7.81 (d, J=7.4 Hz, 2H), 8.03 (s,
1H), 8.22 (d, J=7.8 Hz, 2H), 10.11 ppm (d, J=11.6 Hz, 2H); 13C NMR
(100 MHz, [D6]DMSO): d=34.8, 45.9, 121.1, 121.7, 123.4, 125.6,
126.0, 126.8, 134.2, 134.7, 136.4, 139.9, 143.7, 144.0, 145.7, 162.8,
167.4, 174.6, 176.3 ppm; MS (ES, 70 eV): m/z 458 [M+H]+; elemen-
tal analysis: calcd (%) for C19H15N5O5S2: C 49.88, H 3.30, N 15.31;
found: C 49.92, H 3.39, N 15.36.
(Z)-N’-(3-(5-(4-(Benzyloxy)benzylidene)-4-oxo-2-thioxothiazoli-
din-3-yl)propanoyl)nicotinohydrazide (19): Yield: 79%; mp: 249–
2508C; 1H NMR (400 MHz, [D6]DMSO): d=2.34 (t, J=7.6 Hz, 2H),
4.09 (t, J=8.0 Hz, 2H), 5.17 (s, 2H), 7.11–7.23 (m, 5H), 7.91–8.12 (m,
7H), 8.62 (d, J=6.0 Hz, 1H), 8.80 (s, 1H), 9.92 ppm (d, J=12.4 Hz,
2H); 13C NMR (100 MHz, [D6]DMSO): d=37.6, 48.2, 73.5, 123.7,
124.1 (2C), 124.6, 126.3 (2C), 127.2, 134.2 (2C), 135.3, 136.0, 136.4,
137.3, 138.4, 141.8, 142.4, 142.6, 144.3, 164.1, 167.5, 179.6,
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