736 M. U. Rahman et al.
J Enzyme Inhib Med Chem, 2014; 29(5): 733–743
7.40–7.34 (m, 4H, Ar–H), 7.42 (d, 1H, J ¼ 8.4 Hz, Ar–H), (found) ¼ C 48.89 (48.87), H 2.46 (2.45), N 11.40 (11.38); Ms
8.38–8.32 (m, 4H, Ar–H), 8.54 (t, 1H, J ¼ 6 Hz, J ¼ 10 Hz, Ar–H), (m/z): 493.30 (M þ 2).
8.58 (d, 1H, J ¼ 7.6 Hz, Ar–H), 9.83 (bs, 1H, NH, D2O
exchangeable); % Anal Calcd (found) ¼ C 53.56 (53.54), H 3.21 N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4-
(3.23), N 11.90 (11.92); Ms (m/z): 471.88 (M þ 1).
nitrobenzenesulfonamide (20)
Yield: 72%; m.p. 190–193 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3218 (N–H),
3012 (Ar–CH), 2886 (C–H), 2197 (C–N), 1688 (CO), 1610
(C¼N), 1590, 1476 (C¼C), 1378 (NO2), 1289, 1192 (–SO2–), 612
N-[2-(4-methoxyphenyl)-7-nitro-4-oxoquinazolin-3(4H)yl]-4-
methylbenzenesulfonamide (15)
Yield: 60%; m.p. 180–182 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3282 (N–H), (C–Cl); 1H NMR (DMSO-d6) ꢁ (ppm): 3.15 (s, 3H, OCH3), 7.54–
3056 (Ar–CH), 2877 (C–H), 2184 (C–N), 1723 (CO), 1631 7.51 (m, 4H, Ar–H), 7.62 (d, 1H, J ¼ 9.6 Hz, Ar–H), 8.02 (d, 1H,
(C¼N), 1590, 1476 (C¼C), 1378 (NO2), 1289, 1185 (–SO2–); 1H J ¼ 5.6 Hz, Ar–H), 8.10 (t, 1H, J ¼ 7.2 Hz, J ¼ 6 Hz,
NMR (DMSO-d6) ꢁ (ppm): 2.01(s, 3H, CH3), 3.75 (s, 3H, OCH3), Ar–H),8.16–8.18(m, 4H, Ar–H), 9.34 (bs, 1H, NH, D2O
7.75–7.74 (m, 4H, Ar–H), 7.78 (s, 1H, Ar–H), 8.13 (d, 1H, exchangeable); % Anal Calcd (found) ¼ C 51.80 (51.78), H 3.11
J ¼ 8.8 Hz, Ar–H), 8.17 (t, 1H, J ¼ 6 Hz, J ¼ 7.6 Hz, Ar–H), (3.08), N 11.51 (11.58); Ms (m/z): 487.88 (M þ 1).
8.35–8.33 (m, 4H, Ar–H), 10.03 (bs, 1H, NH, D2O exchangeable);
% Anal Calcd (found) ¼ C 56.65 (56.63), H 3.89 (3.87), N 12.01 N-[7-bromo-2-(4-methylphenyl)-4-oxoquinazolin-3(4H)-yl]-4-
(12.03); Ms (m/z): 465.46 (M ꢀ 1).
nitrobenzenesulfonamide (21)
Yield: 68%; m.p. 157–160 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3310 (N–H),
3072 (Ar–CH), 2890 (C–H), 2178 (C–N), 1680 (CO), 1602
(C¼N), 1588, 1465 (C¼C), 1382 (NO2), 1267, 1190 (–SO2–), 520
N-(7-chloro-4-oxo-2-phenylquinazolin-3(4H)-yl)-4-methylbenze-
nesulfonamide (16)
Yield: 78%; m.p. 150–152 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3302 (N–H), (C–Br); 1H NMR (DMSO-d6) ꢁ (ppm): 2.04 (s, 3H, CH3),
3068 (Ar–CH), 2887 (C–H), 2197 (C–N), 1698 (CO), 1611 7.12–7.13 (m, 4H, Ar–H), 8.02 (d, 1H, J ¼ 7.2 Hz, Ar–H),
1
(C¼N), 1598, 1480 (C¼C), 1279, 1193 (–SO2–), 560 (C–Cl); H 8.10–8.08 (m, 4H, Ar–H), 8.14(t, 1H, J ¼ 9.2 Hz, J ¼ 5.2 Hz,
NMR (DMSO–d6) ꢁ (ppm): 2.05 (s, 3H, CH3), 7.18–7.16 (m, 4H, Ar–H), 8.18 (d, 1H, J ¼ 8.8 Hz, Ar–H), 9.19 (bs, 1H, NH, D2O
Ar–H), 7.18 (d, 1H, J ¼ 5.6, Ar–H), 7.21–7.18 (m, 5H, Ar–H), exchangeable); % Anal Calcd (found) ¼ C 48.94 (48.96), H 2.93
8.10 (t, 1H, J ¼ 8.8 Hz, J ¼ 7.2 Hz, Ar–H), 8.32 (d, 1H, J ¼ 8 Hz, (2.95), N 10.87 (10.85); Ms (m/z): 516.33 (M þ 1).
Ar–H), 10.34 (bs, 1H, NH, D2O exchangeable); % Anal Calcd
(found) ¼ C 59.22 (59.20), H 3.79 (3.77), N 9.87 (9.85); Ms (m/z):
N-[7-bromo-2-(2-chlorophenyl)-4-oxoquinazolin-3(4H)-yl]-4-
426.88 (M þ 1).
nitrobenzenesulfonamide (22)
Yield: 75%; m.p. 200–202 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3270 (N–H),
N-[2-(3-bromophenyl)-7-chloro-4-oxoquinazolin-3(4H)-yl]-4-
methylbenzenesulfonamide (17)
3097 (Ar–CH), 2170 (C–N), 1688 (CO), 1603 (C¼N), 1595, 1465
(C¼C), 1380 (NO2), 1268, 1192 (–SO2–), 715 (C–Cl), 620
(C–Br); 1H NMR (DMSO-d6) ꢁ (ppm): 7.32–7.33 (m, 4H, Ar–H),
7.37 (d, 1H, J ¼ 6.4 Hz, Ar–H), 8.18–8.22 (m, 4H, Ar–H), 8.64
(t, 1H, J ¼ 6.4 Hz, J ¼ 7.2 Hz, Ar–H), 8.84 (d, 1H, J ¼ 7.2 Hz,
Ar–H), 9.54 (bs, 1H, NH, D2O exchangeable); % Anal Calcd
(found) ¼ C 44.84 (44.82), H 2.26 (2.22), N 10.46 (10.42); Ms
(m/z): 537.75 (M þ 2).
Yield: 60%; m.p. 185–187 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3308 (N–H),
3070 (Ar–CH), 2880 (C–H), 2187 (C–N), 1720 (CO), 1618
(C¼N), 1596,1455 (C¼C), 1269, 1191 (–SO2–), 730 (C–Cl), 520
(C–Br); 1H NMR (DMSO-d6) ꢁ (ppm): 2.03 (s, 3H, CH3),
7.08–7.04 (m, 4H, Ar–H), 7.12 (d, 1H, J ¼ 8 Hz, Ar–H), 7.17 (d,
1H, J ¼ 5.2 Hz, Ar–H), 7.21–7.19 (m, 3H, Ar–H), 8.17 (t, 1H,
J ¼ 5.6 Hz, J ¼ 4.4 Hz, Ar–H), 10.44 (bs, 1H, NH, D2O exchange-
able); % Anal Calcd (found) ¼ C 49.57 (49.55), H 3.00 (3.02), N
8.32 (8.34); Ms (m/z): 506.78 (M þ 2).
N-[7-bromo-2-(3-bromophenyl)-4-oxoquinazolin-3(4H)-yl]-4-
nitrobenzenesulfonamide (23)
Yield: 62%; m.p. 290–292 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3285 (N–H),
3085 (Ar–CH), 2174 (C–N), 1685 (CO), 1602 (C¼N), 1595,
N-[7-chloro-2-(4-methylphenyl)-4-oxoquinazolin-3(4H)-yl]-4-
methylbenzenesulfonamide (18)
1
1460 (C¼C), 1382 (NO2), 1275, 1190 (–SO2–), 615 (C–Br); H
Yield: 88%; m.p. 176–178 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3311 (N–H),
3056 (Ar–CH), 2876 (C–H), 2189 (C–N), 1690 (CO), 1612
NMR (DMSO-d6) ꢁ (ppm): 7.22–7.21(m, 4H, Ar–H), 7.31(d,
1H, J ¼ 6.4 Hz, Ar–H), 7.62 (d, 1H, J ¼ 7.2 Hz, Ar–H), 7.70–7.68
(m, 3H, Ar–H), 8.76 (t, 1H, J ¼ 8.8 Hz, J ¼ 8.4 Hz, Ar–H), 9.80
(bs, 1H, NH, D2O exchangeable); % Anal Calcd (found) ¼ C
41.40 (41.38), H 2.08 (2.06), N 9.66 (9.64); Ms (m/z): 582.20
(M þ 2).
1
(C¼N), 1598, 1480 (C¼C), 1279, 1194 (–SO2–), 670 (C–Cl); H
NMR (DMSO-d6) ꢁ (ppm): 2.05 (s, 3H, CH3), 2.34 (s, 3H, CH3),
7.04–7.02 (m, 4H, Ar–H), 8.10 (d, 1H, J ¼ 8.8 Hz, Ar–H),
8.14–8.12 (m, 4H, Ar–H), 8.18 (t, 1H, J ¼ 4.4 Hz, J ¼ 5.6 Hz,
Ar–H), 8.32 (d, 1H, J ¼ 8.8 Hz, Ar–H), 10.40 (bs, 1H, NH, D2O
exchangeable); % Anal Calcd (found) ¼ C 60.07 (60.05), H 4.12
(4.10), N 9.55 (9.57); Ms (m/z): 440.91 (M þ 1).
N-(7-bromo-4-oxo-2-phenylquinazolin-3(4H)-yl)-4-nitrobenzene-
sulfonamide (24)
N-[7-chloro-2-(2-chlorophenyl)-4-oxoquinazolin-3(4H)-yl]-4-
nitrobenzenesulfonamide (19)
Yield: 70%; m.p. 185–187 ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3280 (N–H),
3093 (Ar–CH), 2172 (C–N), 1695 (CO), 1606 (C¼N), 1597, 1478
Yield: 90%; m.p. 122–124ꢂC; IR(KBr) ꢀmax (cmꢀ1): 3304 (N–H), (C¼C), 1377 (NO2), 1285, 1195 (–SO2–), 612 (C–Br); H NMR
1
3038 (Ar–CH), 2192 (C–N), 1699 (CO), 1614 (C¼N), 1594, 1487 (DMSO-d6) ꢁ (ppm): 7.21–7.20 (m, 4H, Ar–H), 7.28(d, 1H,
1
(C¼C), 1375 (NO2), 1288, 1198 (–SO2–), 710 (C–Cl); H NMR J ¼ 9.2, Ar–H), 8.01–8.08 (m, 5H, Ar–H), 8.12 (t, 1H, J ¼ 5.2 Hz,
(DMSO-d6) ꢁ (ppm): 7.10–7.14 (m, 4H, Ar–H), 7.19 (d, 1H, J ¼ 8.8 Hz, Ar–H), 8.38 (d, 1H, J ¼ 8.4 Hz, Ar–H), 9.09 (bs, 1H,
J ¼ 6.4 Hz, Ar–H), 8.28–8.30 (m, 4H, Ar–H), 8.42 (t, 1H, NH, D2O exchangeable); % Anal Calcd (found) ¼ C 47.92
J ¼ 9.6 Hz, J ¼ 7.2 Hz, Ar–H), 8.48 (d, 1H, J ¼ 9.2 Hz, Ar–H), (47.90), H 2.61 (2.65), N 11.18 (11.15); Ms (m/z): 502.31
10.06 (bs, 1H, NH, D2O exchangeable);
%
Anal Calcd (M þ 1).