C.R. Prakash, S. Raja / European Journal of Medicinal Chemistry 46 (2011) 6057e6065
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6.1.2.5.1. 1-Benzylidene-3-(1-(morpholinomethyl)-2,3-dioxoindo-
lin-5-yl)urea (5a). FT-IR (KBr): cmꢀ1 3352 (NHStr); 3038 (Ar
CeHStr); 1710 (C]O, isatin); 1564 (CH]N); 1059 (Cyclic CeOeCstr);
MS (EI) m/z: 408 [Mþ]; Anal. Calcd for C22H21FN4O3: C, 64.70; H,
5.18; N, 13.72. Found: C, 64.83; H, 5.20; N, 13.77.
6.1.2.5.9. 1-(4-nitrobenzylidene)-3-(1-(morpholinomethyl)-2,3-
dioxoindolin-5-yl)urea (5i). FT-IR (KBr): cmꢀ1 3321 (NHStr); 3045
(Ar CeHStr); 1720 (C]O, isatin); 1584 (CH]N); 1526 (AreNO2, N]
O asym); 1344 (AreNO2, N]O sym); 1041 (Cyclic CeOeCstr); 1H
1H NMR (400 MHz, CDCl3,
d
ppm): 2.56 (t, J ¼ 6.2 Hz, 4H, eCH2
morpholine); 3.30 (t, J ¼ 5.8 Hz, 4H, eCH2 morpholine); 4.12 (s, 2H,
eCH2); 6.80e7.52 (m, 8H, AreCH); 8.12 (s, 1H, NH); 8.52 (s, 1H,
CH]N); MS (EI) m/z: 392 [Mþ]; Anal. Calcd for C21H20N4O4: C,
64.28; H, 5.14; N, 14.28. Found: C, 64.12; H, 5.16; N, 14.33.
NMR (400 MHz, CDCl3,
d
ppm): 2.44 (t, J ¼ 6.2 Hz, 4H, eCH2 mor-
pholine); 3.32 (t, J ¼ 5.8 Hz, 4H, eCH2 morpholine); 4.10 (s, 2H,
eCH2); 6.84e7.96 (m, 7H, AreCH); 8.20 (s, 1H, NH); 8.54 (s, 1H,
CH]N); MS (EI) m/z: 437 [Mþ]; Anal. Calcd for C21H19N5O6: C,
57.66; H, 4.38; N, 16.01. Found: C, 57.78; H, 4.40; N, 16.07.1528
(AreNO2, N]O assym.); 1348 (AreNO2, N]O sym.);
6.1.2.5.2. 1-Benzylidene-3-(2,3-dioxo-1-(piperidin-1-ylmethyl)
indolin-5-yl)urea (5b). FT-IR (KBr): cmꢀ1 3386 (NHStr); 3012 (Ar
CeHStr); 1742 (C]O, isatin); 1574 (CH]N); 1H NMR (400 MHz,
CDCl3,
d ppm): 1.20e1.52 (m, 6H, eCH2 piperidinyl); 2.21e2.48 (m,
4H, eCH2 piperidinyl); 4.44 (s, 2H, eCH2); 7.10e7.84 (m, 8H, AreH);
8.42 (s, 1H, NH-Urea); 8.58 (s, 1H, CH]N); MS (EI) m/z 390 [Mþ];
Anal. Calcd for C22H22N4O3: C, 67.68; H, 5.68; N, 14.35. Found: C,
67.81; H, 5.70; N, 14.40.
6.1.2.5.10. 1-(4- nitrobenzylidene)-3-(2,3-dioxo-1-(piperidin-1-
ylmethyl) indolin-5-yl)urea (5j). FT-IR (KBr): cmꢀ1 3372 (NHStr);
3051 (Ar CeHStr); 1744 (C]O, isatin); 1596 (CH]N); 1548
(AreNO2, N]O asym); 1356 (AreNO2, N]O sym); 860 (CeCl); 1H
6.1.2.5.3. 1-(4-chlorobenzylidene)-3-(1-(morpholinomethyl)-2,3-
dioxoindolin-5-yl)urea (5c). FT-IR (KBr): cmꢀ1 3366 (NHStr); 3058
(Ar CeHStr); 1726 (C]O, isatin); 1588 (CH]N,); 1068 (Cyclic
NMR (400 MHz, CDCl3, d ppm): 1.40e1.72 (m, 6H, eCH2 piper-
idinyl); 2.30e2.64 (m, 4H, eCH2 piperidinyl); 4.40 (s, 2H, eCH2);
6.60e7.74 (m, 7H, AreH); 8.25 (s, 1H, NH-Urea); 8.65 (s, 1H, CH]
N); MS (EI) m/z: 435 [Mþ]; Anal. Calcd for C22H21N5O5: C, 60.68; H,
4.86; N, 16.08. Found: C, 60.90; H, 4.88; N, 16.03.
6.1.2.5.11. 1-(3-nitrobenzylidene)-3-(1-(morpholinomethyl)-2,3-
dioxoindolin-5-yl)urea (5k). FT-IR (KBr): cmꢀ1 3378 (NHStr); 3050
(Ar CeHStr); 1732 (C]O, isatin); 1556 (CH]N); 1568 (AreNO2, N]
O asym); 1326 (AreNO2, N]O sym); 1063 (Cyclic CeOeCstr); 1H
CeOeCstr); 850 (CeCl); 1H NMR (400 MHz, CDCl3,
d ppm): 2.55 (t,
J ¼ 6.2 Hz, 4H, eCH2 morpholine); 3.28 (t, J ¼ 5.8 Hz, 4H, eCH2
morpholine); 4.30 (s, 2H, eCH2); 6.88e8.10 (m, 7H, AreCH); 8.22 (s,
1H, NH); 8.78 (s, 1H, CH]N); MS (EI) m/z: 428 [Mþ2]; Anal. Calcd
for C21H19ClN4O4: C, 59.09; H, 4.49; N, 13.13. Found: C, 58.87; H,
4.51; N, 13.18.
6.1.2.5.4. 1-(4-chlorobenzylidene)-3-(2,3-dioxo-1-(piperidin-1-
ylmethyl) indolin-5-yl)urea (5d). FT-IR (KBr): cmꢀ1 3358 (NHStr);
3016 (Ar CeHStr); 1722 (C]O, isatin); 1562 (CH]N); 876 (CeCl); 1H
NMR (400 MHz, CDCl3,
d
ppm): 2.52 (t, J ¼ 6.2 Hz, 4H, eCH2 mor-
pholine); 3.30 (t, J ¼ 5.8 Hz, 4H, eCH2 morpholine); 4.20 (s, 2H,
eCH2); 7.02e7.98 (m, 7H, AreCH); 8.14 (s,1H, NH); 8.38 (s,1H, CH]
N); MS (EI) m/z: 437 [Mþ]; Anal. Calcd for C21H19N5O6: C, 57.66; H,
4.38; N, 16.01. Found: C, 57.48; H, 4.36; N, 16.06.
6.1.2.5.12. 1-(3- nitrobenzylidene)-3-(2,3-dioxo-1-(piperidin-1-
ylmethyl) indolin-5-yl)urea (5l). FT-IR (KBr): cmꢀ1 3384 (NHStr);
3062 (Ar CeHStr); 1730 (C]O, isatin); 1567 (CH]N); 1560
(AreNO2, N]O asym); 1332 (AreNO2, N]O sym); 1H NMR
NMR (400 MHz, CDCl3,
d ppm): 1.23e1.51 (m, 6H, eCH2 piper-
idinyl); 2.34e2.61 (m, 4H, eCH2 piperidinyl); 4.10 (s, 2H, eCH2);
7.23e7.94 (m, 7H, AreH); 8.22 (s, 1H, NH-Urea); 8.48 (s, 1H, CH]
N); MS (EI) m/z: 426 [Mþ2]; Anal. Calcd for C22H21ClN4O3: C, 62.19;
H, 4.98; N, 13.19. Found: C, 62.36; H, 5.00; N, 13.14.
6.1.2.5.5. 1-(2-chlorobenzylidene)-3-(1-(morpholinomethyl)-2,3-
dioxoindolin-5-yl)urea (5e). FT-IR (KBr): cmꢀ1 3376 (NHStr); 3024
(Ar CeHStr); 1732 (C]O, isatin); 1590 (CH]N); 1064 (Cyclic
(400 MHz, CDCl3,
d ppm): 1.33e1.74 (m, 6H, eCH2 piperidinyl);
2.50e2.82 (m, 4H, eCH2 piperidinyl); 4.31 (s, 2H, eCH2); 6.90e7.78
(m, 7H, AreH); 8.19 (s, 1H, NH-Urea); 8.45 (s, 1H, CH]N); MS (EI)
m/z: 435 [Mþ]; Anal. Calcd for C22H21N5O5: C, 60.68; H, 4.86; N,
16.08. Found: C, 60.48; H, 4.84; N, 16.02.
CeOeCstr); 765 (CeCl); 1H NMR (400 MHz, CDCl3,
d ppm): 2.54 (t,
J ¼ 6.0 Hz, 4H, eCH2 morpholine); 3.26 (t, J ¼ 5.8 Hz, 4H, eCH2
morpholine); 4.48 (s, 2H, eCH2); 7.23e8.00 (m, 7H, AreCH); 8.18 (s,
1H, NH); 8.42 (s, 1H, CH]N); MS (EI) m/z: 428 [Mþ2]; Anal. Calcd
for C21H19ClN4O4: C, 59.09; H, 4.49; N, 13.13. Found: C, 59.23; H,
4.51; N, 13.17.
6.1.2.5.6. 1-(2-chlorobenzylidene)-3-(2,3-dioxo-1-(piperidin-1-
ylmethyl) indolin-5-yl)urea (5f). FT-IR (KBr): cmꢀ1 3350 (NHStr);
2986 (Ar CeHStr); 1718 (C]O, isatin); 1546 (CH]N); 748 (CeCl); 1H
6.1.2.5.13. 1-(4-bromobenzylidene)-3-(1-(morpholinomethyl)-2,3-
dioxoindolin-5-yl)urea (5m). FT-IR (KBr): cmꢀ1 3358 (NHStr); 3010
(Ar CeHStr); 1712 (C]O, isatin); 1578 (CH]N); 1032 (Cyclic
CeOeCstr); 632 (CeBr); 1H NMR (400 MHz, CDCl3,
d ppm): 2.55 (t,
J ¼ 5.8 Hz, 4H, eCH2 morpholine); 3.36 (t, J ¼ 5.6 Hz, 4H, eCH2
morpholine); 4.45 (s, 2H, eCH2); 7.13e7.85 (m, 7H, AreCH); 8.13 (s,
1H, NH); 8.60 (s, 1H, CH]N); MS (EI) m/z: 472 [Mþ2]; Anal. Calcd
for C21H19BrN4O4: C, 53.52; H, 4.06; N, 11.89. Found: C, 53.36; H,
4.04; N, 11.93.
6.1.2.5.14. 1-(4-bromobenzylidene)-3-(2,3-dioxo-1-(piperidin-1-
ylmethyl) indolin-5-yl)urea (5n). FT-IR (KBr): cmꢀ1 3365 (NHStr);
3021 (Ar CeHStr); 1741 (C]O, isatin); 1539 (CH]N); 662 (CeBr); 1H
NMR (400 MHz, CDCl3,
d ppm): 1.19e1.47 (m, 6H, eCH2 piper-
idinyl); 2.44e2.72 (m, 4H, eCH2 piperidinyl); 4.16 (s, 2H, eCH2);
7.04e7.84 (m, 7H, AreH); 8.11 (s, 1H, NH-Urea); 8.54 (s, 1H, CH]N);
MS (EI) m/z: 426 [Mþ2]; Anal. Calcd for C22H21ClN4O3: C, 62.19; H,
4.98; N, 13.19. Found: C, 62.39; H, 4.96; N, 13.14.
6.1.2.5.7. 1-(4-fluorobenzylidene)-3-(1-(morpholinomethyl)-2,3-
dioxoindolin-5-yl)urea (5g). FT-IR (KBr): cmꢀ1 3392 (NHStr); 3022
(Ar CeHStr); 1744 (C]O, isatin); 1570 (CH]N); 1067 (Cyclic
NMR (400 MHz, CDCl3,
d ppm): 1.11e1.50 (m, 6H, eCH2 piper-
idinyl); 2.15e2.60 (m, 4H, eCH2 piperidinyl); 4.12 (s, 2H, eCH2);
6.90e7.82 (m, 7H, AreH); 8.30 (s, 1H, NH-Urea); 8.64 (s, 1H, CH]
N); MS (EI) m/z: 470 [Mþ2]; Anal. Calcd for C22H21BrN4O3: C, 56.30;
H, 4.51; N, 11.94. Found: C, 56.48; H, 4.53; N, 11.98.
CeOeCstr); 1112 (CeF); 1H NMR (400 MHz, CDCl3,
d ppm): 2.40 (t,
J ¼ 5.6 Hz, 4H, eCH2 morpholine); 3.36 (t, J ¼ 5.6 Hz, 4H, eCH2
morpholine); 4.22 (s, 2H, eCH2); 6.98e7.84 (m, 7H, AreCH); 8.16 (s,
1H, NH); 8.64 (s, 1H, CH]N); MS (EI) m/z: 410 [Mþ]; Anal. Calcd for
C21H19FN4O4: C, 61.46; H, 4.67; N, 13.65. Found: C, 61.67; H, 4.69; N,
13.60.
6.1.2.5.15. 1-(4-hydroxybenzylidene)-3-(1-(morpholinomethyl)-
2,3-dioxoindolin-5-yl)urea (5o). FT-IR (KBr): cmꢀ1 3510 (OHstr);
3362 (NHStr); 3020 (Ar CeHStr); 1743 (C]O, isatin); 1546 (CH]N);
6.1.2.5.8. 1-(4-fluorobenzylidene)-3-(2,3-dioxo-1-(piperidin-1-
ylmethyl) indolin-5-yl)urea (5h). FT-IR (KBr): cmꢀ1 3326 (NHStr);
3032 (Ar CeHStr); 1736 (C]O, isatin); 1566 (CH]N); 1126 (CeF);
1056 (Cyclic CeOeCstr); 1H NMR (400 MHz, CDCl3,
d ppm): 2.50 (t,
J ¼ 6.0 Hz, 4H, eCH2 morpholine); 3.32 (t, J ¼ 5.6 Hz, 4H, eCH2
morpholine); 4.55 (s, 2H, eCH2); 5.02 (s, 1H, OH); 6.92e7.82 (m, 7H,
AreCH); 8.35 (s, 1H, NH); 8.74 (s, 1H, CH]N); MS (EI) m/z: 408
[Mþ]; Anal. Calcd for C21H20N4O5: C, 61.76; H, 4.94; N, 13.72. Found:
C, 61.70; H, 4.96; N, 13.77.
1H NMR (400 MHz, CDCl3,
d ppm): 1.45e1.76 (m, 6H, eCH2 piper-
idinyl); 2.49e2.81 (m, 4H, eCH2 piperidinyl); 3.98 (s, 2H, eCH2);
7.12e7.77 (m, 7H, AreH); 8.33 (s, 1H, NH-Urea); 8.51 (s, 1H, CH]N);