S.K. Bhati, A. Kumar / European Journal of Medicinal Chemistry 43 (2008) 2323e2330
2329
Table 5
Spectral data of compounds (6ae8h)
Compound
[M]þ at m/z
1H NMR (CDCl3 þ DMSOd6)
6.82e7.30 (m, 9H, Ar-H), 4.65 (d, 2H, NHeCH2), 5.90
IR (KBr) in cmꢂ1
6a
403
3042 (CeH), 1572 (C]N), 3270 (NeH), 1290 (NeN),
728 (CeSeC)
(t, 1H, NH2), 7.98 (s, 1H, CH-Ar)
6b
6c
[M]þ437 [M þ 1]þ 438
[M þ 2]þ 439
433
6.85e7.28 (m, 8H, Ar-H), 4.68 (d, 2H, NHeCH2), 5.94
(t, 1H, NH2), 7.95 (s, 1H, CH-Ar)
3045 (CeH), 1570 (C]N), 3275 (NeH), 1295 (NeN),
730 (CeSeC)
6.80e7.25 (m, 8H, Ar-H), 4.70 (d, 2H, NHeCH2), 5.88
(t, 1H, NH2), 7.97 (s, 1H, CH-Ar), 3.28 (s, 3H,
Ar-OCH3)
3050 (CeH), 1575 (C]N), 3278 (NeH), 1285 (NeN),
735 (CeSeC), 1165(CeOeC), 1695 (C]O)
6d
6e
419
446
6.82e7.20 (m, 8H, Ar-H), 4.78 (d, 2H, NHeCH2), 5.80
(t, 1H, NH), 8.02 (s, 1H, CH-Ar), 9.98 (s, 1H, Ar-OH)
7.05e7.35 (m, 8H, Ar-H), 4.72 (d, 2H, NHeCH2), 5.85
(t, 1H, NH), 8.10 (s, 1H, CH-Ar), 2.94 (s, 6H,
Ar-N(CH3)2)
3040 (CeH), 1580 (C]N), 3280 (NeH), 1295 (NeN),
725 (CeSeC), 1690 (C]O)
3035 (CeH), 1585 (C]N), 3285 (NeH), 1280 (NeN),
705 (CeSeC)
6f
417
6.95e7.25 (m, 8H, Ar-H), 4.67 (d, 2H, NHeCH2), 5.90
(t, 1H, NH), 8.05 (d, 1H, CH-Ar), 3.68 (s, 3H, Ar-CH3)
7.00e7.28 (m, 8H, Ar-H), 4.75 (d, 2H, NHeCH2), 5.98
(t, 1H, NH), 7.90 (s, 1H, CH-Ar)
3030 (CeH), 1582 (C]N), 3283 (NeH), 1282 (NeN),
698 (CeSeC)
3032 (CeH), 3278 (NeH), 1572 (C]N), 1290 (NeN),
725 (CeSeC), 668 (CeCl)
6g
6h
[M]þ437 [M þ 1]þ 438
[M þ 2]þ 439
433
6.90e7.32 (m, 8H, Ar-H), 4.80 (d, 2H, NHeCH2), 5.92
(t, 1H, NH), 7.87 (s, 1H, CH-Ar), 3.35 (s, 3H,
Ar-OCH3)
3037 (CeH), 1578 (C]N), 3287 (NeH), 1280 (NeN),
720 (CeSeC), 1168 (CeOeC), 1685 (C]O)
7a
7b
7c
7d
7e
7f
477
7.05e7.70 (m, 9H, Ar-H), 4.50 (d, 2H, NHeCH2), 6.08
(t, 1H, NH), 4.40 (s, 1H, CHeN), 2.85 (s, 2H, CH2)
3030 (CeH), 1590 (C]N), 3295 (NeH), 1270 (NeN),
710 (CeSeC), 1480 (CeN of eNeCH-Ar), 1695
(C]O)
3025 (CeH), 1595 (C]N), 3320 (NeH), 1275 (NeN),
715 (CeSeC), 1485 (CeN of eNeCH-Ar), 670
(CeCl), 1690 (C]O)
3035 (CeH), 1585 (C]N), 3325 (NeH), 1280 (NeN),
705 (CeSeC), 1482 (CeN of eNeCH-Ar), 1170
(CeOeC), 1700 (C]O)
[M]þ511 [M þ 1]þ 512
[M þ 2]þ 513
7.10e7.75 (m, 8H, Ar-H), 4.60 (d, 2H, NHeCH2), 6.10
(t, 1H, NH), 4.36 (s, 1H, CHeN), 2.90 (s, 2H, CH2)
507
493
520
491
7.15e7.80 (m, 8H, Ar-H), 4.57 (d, 2H, NHeCH2), 6.12
(t, 1H, NH), 4.30 (s, 1H, CHeN), 3.40 (s, 3H,
Ar-OCH3), 2.86 (s, 2H, CH2)
7.12e7.77 (m, 8H, Ar-H), 4.62 (d, 2H, NHeCH2), 6.09
(t, 1H, NH), 4.38 (s, 1H, CHeN), 9.95 (s, 1H, Ar-OH),
2.82 (s, 2H, CH2)
3038 (CeH), 1600 (C]N), 3330 (NeH), 1265 (NeN),
700 (CeSeC), 1475 (CeN of eNeCH-Ar), 3415
(OH), 1680 (C]O)
7.10e7.72 (m, 8H, Ar-H), 4.65 (d, 2H, NHeCH2), 6.15
(t, 1H, NH), 4.42 (s, 1H, CHeN), 2.80 (s, 2H, CH2),
2.98 (s, 6H, Ar-N(CH3)2)
3022 (CeH), 1588 (C]N), 3322 (NeH), 1270 (NeN),
720 (CeSeC), 1460 (CeN of eNeCH-Ar), 1688
(C]O)
7.06e7.70 (m, 8H, Ar-H), 4.70 (d, 2H, NHeCH2), 6.12
(t, 1H, NH), 4.36 (s, 1H, CHeN), 2.85 (s, 2H, CH2),
3.70 (s, 3H, Ar-CH3)
3020 (CeH), 1592 (C]N), 3328 (NeH), 1278 (NeN),
725 (CeSeC), 1465 (CeN of eNeCH-Ar), 1692
(C]O)
7g
7h
8a
8b
8c
8d
8e
8f
[M]þ511 [M þ 1]þ 512
[M þ 2]þ 513
6.95e7.62 (m, 8H, Ar-H), 4.54 (d, 2H, NHeCH2), 6.11
(t, 1H, NH), 4.32 (s, 1H, CHeN), 2.87 (s, 2H, CH2)
3025 (CeH), 1598 (C]N), 3335 (NeH), 1280 (NeN),
730 (CeSeC), 1472 (CeN of eNeCH-Ar), 1698
(C]O), 675 (CeCl)
3015 (CeH), 1594 (C]N), 3320 (NeH), 1285 (NeN),
728 (CeSeC), 1477 (CeN of eNeCH-Ar), 1695
(C]O)
507
6.98e7.75 (m, 8H, Ar-H), 4.55 (d, 2H, NHeCH2), 6.05
(t, 1H, NH), 3.44 (s, 3H, Ar-OCH3), 4.34 (s, 1H,
CHeN), 2.87 (s, 2H, CH2)
[M]þ479 [M þ 1]þ 480
[M þ 2]þ 481
7.08e7.68 (m, 9H, Ar-H), 4.50 (d, 2H, NHeCH2), 6.02
(t, 1H, NH), 4.35 (d, 1H, eNeCH), 4.82 (d, 1H,
CHeCl)
3020 (CeH), 1585 (C]N), 3310 (NeH), 1280 (NeN),
715 (CeSeC), 1485 (CeN of eNeCH-Ar), 1690
(C]O), 675 (CeCl)
[M]þ514 [M þ 1]þ 515
7.12e7.73 (m, 8H, Ar-H), 4.52 (d, 2H, NHeCH2), 6.05
(t, 1H, NH), 4.38 (d, 1H, eNeCH), 4.85 (d, 1H,
CHeCl)
3015 (CeH), 1590 (C]N), 3315 (NeH), 1275 (NeN),
720 (CeSeC), 1480 (CeN of eNeCH-Ar), 670
(CeCl), 1685 (C]O)
[M þ 2]þ 516
[M]þ509 [M þ 1]þ 510
[M þ 2]þ 511
7.15e7.70 (m, 8H, Ar-H), 4.55 (d, 2H, NHeCH2), 6.10
(t, 1H, NH), 4.42 (d, 1H, eNeCH), 4.80 (d, 1H,
CHeCl), 3.42 (s, 3H, Ar-OCH3)
3025 (CeH), 1580 (C]N), 3320 (NeH), 1290 (NeN),
710 (CeSeC), 1170 (CeOeC), 1695 (C]O), 677
(CeCl), 1475 (CeN of eNeCH-Ar).
[M]þ495 [M þ 1]þ 496
7.10e7.65 (m, 8H, Ar-H), 4.60 (d, 2H, NHeCH2), 6.15
(t, 1H, NH), 4.45 (d, 1H, eNeCH), 4.88 (d, 1H,
CHeCl), 10.12 (s, 1H, Ar-OH)
7.05e7.72 (m, 8H, Ar-H), 4.57 (d, 2H, NHeCH2), 6.12
(t, 1H, NH), 4.39 (d, 1H, eNeCH), 4.84 (d, 1H,
CHeCl), 2.92 (s, 6H, Ar-N(CH3)2
3010 (CeH), 1600 (C]N), 3325 (NeH), 1265 (NeN),
710 (CeSeC), 1495 (CeN of eNeCH-Ar), 3410
(OH), 1680 (C]O), 665 (CeCl)
3015 (CeH), 1595 (C]N), 3320 (NeH), 1270 (NeN),
715 (CeSeC), 1490 (CeN of eNeCH-Ar), 3410
(OH), 1690 (C]O), 670(CeCl)
[M þ 2]þ 497
[M]þ522 [M þ 1]þ 523
[M þ 2]þ 524
[M]þ493 [M þ 1]þ 494
6.97e7.62 (m, 8H, Ar-H), 4.54 (d, 2H, NHeCH2), 6.18
(t, 1H, NH), 4.33 (d, 1H, eNeCH), 4.89 (d, 1H,
CHeCl), 3.65 (s, 3H, Ar-CH3)
3020 (CeH), 1590 (C]N), 3315 (NeH), 1275 (NeN),
720 (CeSeC), 1485 (CeN of eNeCH-Ar), 1685
(C]O), 675 (CeCl)
[M þ 2]þ 495