10
S. Malik et al. / European Journal of Medicinal Chemistry 67 (2013) 1e13
exchangeable); 13C NMR (
d
) DMSO-d6: 25.9 (C-11), 112.5 (C-70), 118.7
AreH of benzothiazole), 7.85 (d, 1H, AreH of benzothiazole), 8.30
(d, 1H, AreH at C6eH quinazoline), 8.64 (s, 1H, AreH at C8eH qui-
nazoline), 8.80 (br s, 1H of NHC]O, D2O exchangeable), 12.72 (br s,
(C-60), 120.3 (C-40), 123.5 (C-8), 125.8 (C-6), 127.7 (C-50), 128.5 (C-10),
130.6 (C-5), 134.5 (C-7), 131.5 (C-90), 143.4 (C-80), 145.4 (C-9), 152.5
(C]O),162.2 (C-2),164.6 (C-20),168.5 (C-4),186.6 (C]S); MS (m/z, %):
509.70 (Mþ þ 1 for 35,37Cl and 79,81Br, 100), 508.25 (Mþ þ 1 for 35Cl
and 79Br, 72.23), 511.92 (Mþ þ 1 for 37Cl and 81Br, 70.13).
1H of NHC]S, D2O exchangeable); 13C NMR (
d) DMSO-d6: 24.6 (C-
11), 116.4 (C-70), 118.7 (C-60), 120.5 (C-40), 122.6 (C-8), 126.5 (C-50),
127.5 (C-6), 128.8 (C-10), 130.2 (C-5), 131.5 (C-90), 135.7 (C-7), 146.4
(C-80), 148.6 (C-9), 155.5 (C]O), 162.2 (C-2), 164.6 (C-20), 168.5 (C-
4),186.2 (C]S); MS (m/z, %): 465.20 (Mþ þ 1 for 35,35Cl, 100), 466.34
(Mþ þ 1 for 35,37Cl, 75.43), 470.41 (Mþ þ 1 for 37,37Cl, 18.38).
4.1.1.14. 7-Chloro-2-methyl-4-oxo-(6-(trifluoromethoxy)benzo[d]
thiazol-2-ylcarbamoyl) quinazoline-3(4H)-carbothioamide (SA 14).
IR (KBr) nmax (cmꢀ1): 3440 (Secondary amide NH), 3055 (AreCH),
2899 (Aliphatic CH), 1640 (C]O of quinazoline), 1615 (C]O of
urea), 1520 (C]N), 1322 (CeF), 1170 (CeOCF3), 1055 (C]S), 670 (Ce
4.1.1.18. 7-Chloro-(5-chlorobenzo[d]thiazol-2-ylcarbamoyl)-2-
methyl-4-oxoquinazoline-3(4H)-carbothioamide (SA 18). IR (KBr)
nmax (cmꢀ1): 3435 (Secondary amide NH), 3065 (AreCH), 2975
(Aliphatic CH), 1675 (C]O of quinazoline), 1625 (C]O of urea),
1555 (C]N), 1060 (C]S), 834, 810 (CeCl), 685 (CeSeC); 1H NMR
SeC); 1H NMR (
d) DMSO-d6: 2.47 (s, 3H, quinazolineeCH3), 6.99 (d,
1H, AreH of benzothiazole), 7.10 (d, 1H, AreH at C5eH quinazoline),
7.45 (d, 1H, AreH of benzothiazole), 7.85 (s, 1H, AreH of benzo-
thiazole), 8.25 (d, 1H, AreH at C6eH quinazoline), 8.30 (s, 1H, AreH
at C8eH quinazoline), 8.99 (br s, 1H of NHC]O, D2O exchangeable),
(d) DMSO-d6: 2.43 (s, 3H, quinazolineeCH3), 7.15 (d, 1H, AreH of
benzothiazole), 7.30 (d,1H, AreH of benzothiazole), 7.50 (d, 1H, Are
H at C5eH quinazoline), 7.86 (s, 1H, AreH of benzothiazole), 7.99 (br
s, 1H of NHC]O, D2O exchangeable), 8.23 (d, 1H, AreH at C6eH
quinazoline), 8.48 (s, 1H, AreH at C8eH quinazoline), 11.51 (br s, 1H
11.44 (br s, 1H of NHC]S, D2O exchangeable); 13C NMR (
d) DMSO-
d6: 26.1 (C-11), 106.5 (C-70), 116.8 (C-50), 119.7 (C-40), 120.2 (eOCF3),
122.5 (C-8), 126.4 (C-6), 127.8 (C-10), 130.5 (C-5), 132.1 (C-90), 135.5
(C-7), 145.4 (C-80), 146.7 (C-9), 152.8 (C]O), 156.4 (C-60), 162.5 (C-
2), 165.6 (C-20), 167.6 (C-4), 186.6 (C]S); MS (m/z, %): 514.91
(Mþ þ 1 for 35Cl, 100), 516.52 (Mþ þ 1 for 37Cl, 32.45).
of NHC]S, D2O exchangeable); 13C NMR (
d) DMSO-d6: 27.1 (C-11),
118.7 (C-70), 120.2 (C-40), 122.2 (C-60), 122.8 (C-8), 126.5 (C-6), 127.4
(C-50),128.5 (C-10),131.5 (C-5),132.5 (C-90),134.9 (C-7),145.5 (C-80),
149.6 (C-9), 155.5 (C]O), 161.2 (C-2), 164.6 (C-20), 168.5 (C-4), 186.2
(C]S); MS (m/z, %): 465.11 (Mþ þ 1 for 35,35Cl, 100), 466.28 (Mþ þ 1
for 35,37Cl, 80.11), 470.46 (Mþ þ 1 for 37,37Cl, 19.35).
4.1.1.15. 7-Chloro-(6-hydroxybenzo[d]thiazol-2-ylcarbamoyl)-2-
methyl-4-oxoquinazoline-3(4H)-carbothioamide (SA 15). IR (KBr) nmax
(cmꢀ1): 3445 (Secondary amide NH), 3095 (AreCH), 2985 (Aliphatic
CH), 1665 (C]O of quinazoline), 1635 (C]O of urea), 1535 (C]N),
4.1.1.19. 7-Chloro-2-methyl-(6-methylbenzo[d]thiazol-2-ylcarbamoyl)-
4-oxoquinazoline-3(4H)-carbothioamide (SA 19). IR (KBr) nmax
(cmꢀ1): 3445 (Secondary amide NH), 3055 (AreCH), 2950 (Aliphatic
CH), 1660 (C]O of quinazoline), 1625 (C]O of urea), 1535 (C]N),
1220 (CeO),1055 (C]S), 670 (CeSeC); 1H NMR (
d) DMSO-d6: 2.48 (s,
3H, quinazolineeCH3), 6.95 (d, 1H, AreH of benzothiazole), 7.05 (d,
1H, AreH at C5eH quinazoline), 7.20 (d, 1H, AreH of benzothiazole),
7.88 (s, 1H, AreH of benzothiazole), 8.28 (d, 1H, AreH at C6eH qui-
nazoline), 8.35 (s, 1H, AreH at C8eH quinazoline), 8.98 (br s, 1H of
NHC]O, D2O exchangeable), 10.48 (s, 1H AreOH of benzothiazole),
1055 (C]S), 834 (CeCl), 675 (CeSeC); 1H NMR (
d) DMSO-d6: 2.40 (s,
3H, quinazolineeCH3), 2.65 (s, 3H, AreCH3 of benzothiazole), 7.10 (d,
1H, AreH of benzothiazole), 7.37 (d,1H, AreH of benzothiazole), 7.60
(d, 1H, AreH at C5eH quinazoline), 7.85 (s, 1H, AreH of benzothia-
zole), 8.20 (d, 1H, AreH at C6eH quinazoline), 8.25 (s, 1H, AreH at
C8eH quinazoline), 8.36 (br s, 1H of NHC]O, D2O exchangeable),
12.98 (br s,1H of NHC]S, D2O exchangeable); 13C NMR (
d) DMSO-d6:
24.4 (C-11), 117.6 (C-70), 120.5 (C-50), 122.8 (C-8), 125.2 (C-40), 126.4
(C-6), 129.8 (C-10), 132.2 (C-5), 133.5 (C-90), 136.2 (C-7), 145.4 (C-80),
148.6 (C-9), 150.5 (C-60), 154.4 (C]O), 158.8 (C-2), 161.2 (C-20), 165.4
(C-4), 188.6 (C]S); MS (m/z, %): 446.95 (Mþ þ 1 for 35Cl, 99.70),
548.52 (Mþ þ 1 for 37Cl, 38.40).
12.31 (br s,1H of NHC]S, D2O exchangeable); 13C NMR (
d) DMSO-d6:
20.5 (eCH3), 26.5 (C-11), 109.5 (C-70), 118.7 (C-50), 121.6 (C-40), 122.2
(C-8), 126.5 (C-6), 128.5 (C-10), 129.9 (C-60), 130.8 (C-5), 131.5 (C-90),
136.1 (C-7), 145.4 (C-80), 147.6 (C-9), 152.5 (C]O), 160.2 (C-2), 162.2
(C-20), 169.5 (C-4), 185.8 (C]S); MS (m/z, %): 444.95 (Mþ þ 1 for 35Cl,
100), 446.52 (Mþ þ 1 for 37Cl, 38.60).
4.1.1.16. 7-Chloro-(6-methoxybenzo[d]thiazol-2-ylcarbamoyl)-2-
methyl-4-oxoquinazoline-3(4H)-carbothioamide (SA 16). IR (KBr) nmax
(cmꢀ1): 3450 (Secondary amide NH), 3010 (AreCH), 2985 (Aliphatic
CH), 1675 (C]O of quinazoline), 1635 (C]O of urea), 1535 (C]N),
4.1.1.20. (4-Bromobenzo[d]thiazol-2-ylcarbamoyl)-7-chloro-2-methyl-
4-oxoquinazoline-3(4H)-carbothioamide (SA 20). IR (KBr) nmax
(cmꢀ1): 3435 (Secondary amide NH), 3070 (AreCH), 2986 (Aliphatic
CH), 1655 (C]O of quinazoline), 1635 (C]O of urea), 1525 (C]N),
1185 (AreOCH3), 1045 (C]S), 825 (CeCl), 670 (CeSeC); 1H NMR (
d)
DMSO-d6: 2.40 (s, 3H, quinazolineeCH3), 3.65 (s, 3H AreOCH3 of
benzothiazole), 6.95 (d,1H, AreH of benzothiazole), 7.15 (d,1H, AreH
at C5eH quinazoline), 7.35 (d, 1H, AreH of benzothiazole), 7.85 (s,1H,
AreH of benzothiazole), 8.34 (d,1H, AreH at C6eH quinazoline), 8.52
(s, 1H, AreH at C8eH quinazoline), 8.73 (br s, 1H of NHC]O, D2O
exchangeable), 12.08 (br s, 1H of NHC]S, D2O exchangeable); 13C
1055 (C]S), 670 (CeSeC), 590 (CeBr); 1H NMR (
d) DMSO-d6: 2.45 (s,
3H, quinazolineeCH3), 6.95 (d, 1H, AreH of benzothiazole), 7.22 (t,
1H, AreH of benzothiazole), 7.45 (d, 1H, AreH at C5eH quinazoline),
7.95 (d, 1H, AreH of benzothiazole), 8.23 (d, 1H, AreH at C6eH qui-
nazoline), 8.55 (s, 1H, AreH at C8eH quinazoline), 9.15 (br s, 1H of
NHC]O, D2O exchangeable), 11.30 (br s, 1H of NHC]S, D2O
NMR (d
) DMSO-d6: 26.2 (C-11), 50.2 (eOCH3), 108.5 (C-70), 118.4 (C-
50),121.6 (C-40),124.2 (C-8),126.5 (C-6),127.9 (C-10),131.5 (C-5),132.5
(C-90), 135.4 (C-7), 145.5 (C-80), 148.6 (C-9), 152.5 (C]O), 154.4 (C-60),
161.5 (C-2), 164.6 (C-20),168.5 (C-4), 185.6 (C]S); MS (m/z, %): 460.95
(Mþ þ 1 for 35Cl, 100), 462.52 (Mþ þ 1 for 37Cl, 35.60).
exchangeable); 13C NMR ( ) DMSO-d6: 26.1 (C-11), 114.4 (C-40), 119.2
d
(C-70), 122.5 (C-8), 126.2 (C-60), 128.2 (C-50), 127.5 (C-6), 128.8 (C-10),
130.5 (C-5), 136.3 (C-7), 131.5 (C-90), 144.4 (C-80), 148.6 (C-9), 154.3
(C]O),158.4 (C-2),162.5 (C-20),168.5 (C-4),186.2 (C]S); MS (m/z, %):
509.66 (Mþ þ 1 for 35,37Cl and 79,81Br, 100), 508.15 (Mþ þ 1 for 35Cl
and 79Br, 74.28), 511.82 (Mþ þ 1 for 37Cl and 81Br, 72.53).
4.1.1.17. 7-Chloro-(4-chlorobenzo[d]thiazol-2-ylcarbamoyl)-2-
methyl-4-oxoquinazoline-3(4H)-carbothioamide (SA 17). IR (KBr)
nmax (cmꢀ1): 3433 (Secondary amide NH), 3055 (AreCH), 2970
(Aliphatic CH), 1665 (C]O of quinazoline), 1625 (C]O of urea),
1550 (C]N), 1060 (C]S), 834, 820 (CeCl), 680 (CeSeC); 1H NMR
4.1.1.21. (6-Fluorobenzo[d]thiazol-2-ylcarbamoyl)-2-methyl-4-
oxoquinazoline-3(4H)-carbothioamide (SA 21). IR (KBr) nmax (cmꢀ1):
3425 (Secondary amide NH), 3060, 3040 (AreCH), 2925 (Aliphatic
CH), 1654 (C]O of quinazoline), 1640 (C]O of urea), 1525 (C]N),
(d) DMSO-d6: 2.40 (s, 3H, quinazolineeCH3), 6.91 (d, 1H, AreH of
benzothiazole), 7.10 (d, 1H, AreH at C5eH quinazoline), 7.40 (t, 1H,