6
R. P. Modh et al.
Arch. Pharm. Chem. Life Sci. 2012, 000, 1–9
d ppm): 2.44 (s, 3H, Ar–CH3), 3.74 (s, 3H, –OCH3), 3.88 (s,
–
2-(3,4,5-Trimethoxystyryl)-4-(4-chlorophenyl ureido)-
quinazoline (7d)
6H, 2x–OCH ), 6.56 (d, 1H, J ¼ 15, –CH CH), 8.02 (d, 1H,
–
3
–
J ¼ 16, –CH CH), 8.86 (s, 1H, –NH), 9.42 (s, 1H, –NH), 6.61 (d,
Yield (73%), mp 158–1608C; IR (KBr) (cmꢀ1): 1732 (C C str. a, b
–
–
–
unsat.), 1620 (C N str.), 1572 (C O str. in urea), 3343 (–NH str.),
2H, J ¼ 7, aromatic), 6.68 (dd, 1H, J ¼ 7.45, 2.35, Ar–H), 6.74 (dd,
1H, J ¼ 8.47, 2.26, Ar–H), 7.22–7.84 (m, 6H, Ar–H). 13C NMR
(75 MHz; DMSO-d6; d ppm): 24.30, 56.12, 56.42, 103.80, 112.70,
115.62, 119.73, 121.52, 126.22, 128.80, 129.22, 129.52, 132.83,
133.43, 133.82, 134.02, 138.43, 149.72, 150.72, 151.90, 169.90,
170.00. MS, m/z: [Mþ1]þ 471.20. Anal. calcd. for C27H26N4O4: C,
68.92; H, 5.57; N, 11.91. Found C, 68.87; H, 5.58; N, 11.86.
–
–
–
–
1547 (–NH def.), 813 (C–O–C assym.), 1242 (C–O–C sym.),
724 (C–Cl str. in aromatic ring); 1H NMR (300 MHz; DMSO-d6;
d ppm): 3.75 (s, 3H, –OCH3), 3.86 (s, 6H, 2x–OCH3), 6.54 (d, 1H,
–
–
J ¼ 15, –CH CH), 8.03 (d, 1H, J ¼ 16, –CH CH), 8.85 (s, 1H, –NH),
–
–
9.44 (s, 1H, –NH), 6.63 (d, 2H, J ¼ 7, aromatic), 6.69 (dd, 1H,
J ¼ 7.32, 2.18, Ar–H), 6.74 (dd, 1H, J ¼ 8.34, 2.12, Ar–H),
7.22–7.84 (m, 6H, Ar–H). 13C NMR (75 MHz; DMSO-d6; d ppm):
56.10, 56.40, 103.82, 112.72, 115.62, 119.70, 124.40, 126.20,
128.83, 129.52, 130.40, 133.42, 133.80, 134.52, 138.44, 149.71,
150.75, 151.93, 169.90, 170.02. MS, m/z: [Mþ1]þ 491.14. Anal.
calcd. for C26H23N4O4Cl: C, 63.61; H, 4.72; N, 11.41. Found C,
63.58; H, 4.69; N, 11.36.
2-(3,4,5-Trimethoxystyryl)-4-(2-methoxyphenyl ureido)-
quinazoline (7h)
Yield (62%), mp 152–1558C; IR (KBr) (cmꢀ1): 1732 (C C str. a, b
–
–
unsat.), 1622 (C N str.), 1573 (C O str. in urea), 3342 (–NH str.),
–
–
–
–
1545 (–NH def.), 810 (C–O–C assym.), 1240 (C–O–C sym.); 1H NMR
(300 MHz; DMSO-d6; d ppm): 3.76 (s, 3H, –OCH3), 3.87 (s,
–
6H, 2x–OCH ), 6.55 (d, 1H, J ¼ 14, –CH CH), 8.01 (d, 1H,
–
3
–
–
2-(3,4,5-Trimethoxystyryl)-4-(2-methyl phenyl ureido)-
quinazoline (7e)
J ¼ 16, –CH CH), 8.85 (s, 1H, –NH), 9.43 (s, 1H, –NH), 6.63 (d,
2H, J ¼ 7, aromatic), 6.70 (dd, 1H, J ¼ 7.55, 2.39, Ar–H), 6.73 (dd,
1H, J ¼ 8.38, 2.52, Ar–H), 7.22–7.84 (m, 6H, Ar–H), 3.69 (s, 3H,
Ar–OCH3). 13C NMR (75 MHz; DMSO-d6; d ppm): 55.82, 56.12,
56.43, 103.82, 112.72, 114.52, 115.63, 119.72, 121.32, 122.63,
124.23, 125.40, 126.22, 128.82, 129.52, 133.43, 133.82, 138.46,
149.73, 150.72, 151.90, 152.72, 169.92, 170.02. MS, m/z: [Mþ1]þ
486.19. Anal. calcd. for C27H26N4O5: C, 66.65; H, 5.39; N, 11.52.
Found C, 66.55; H, 5.37; N, 11.48.
Yield (65%), mp 139–1428C; IR (KBr) (cmꢀ1): 1733 (C C str. a, b
–
–
unsat.), 1622 (C N str.), 1578 (C O str. in urea), 3340 (–NH str.),
–
–
–
–
1543 (–NH def.), 811 (C–O–C assym.), 1243 (C–O–C sym.), 1390
(C–CH3 str. in aromatic ring); 1H NMR (300 MHz; DMSO-d6;
d ppm): 2.46 (s, 3H, Ar–CH3), 3.74 (s, 3H, –OCH3), 3.88 (s,
–
6H, 2x–OCH ), 6.56 (d, 1H, J ¼ 14, –CH CH), 8.02 (d, 1H,
–
3
–
–
J ¼ 15, –CH CH), 8.86 (s, 1H, –NH), 9.42 (s, 1H, –NH), 6.61 (d,
2H, J ¼ 7, aromatic), 6.68 (dd, 1H, J ¼ 7.25, 2.31, Ar–H), 6.74 (dd,
1H, J ¼ 8.29, 2.35, Ar–H), 7.22–7.84 (m, 6H, Ar–H). 13C NMR
(75 MHz; DMSO-d6; d ppm): 18.8, 56.10, 56.42, 103.82, 112.75,
115.61, 119.75, 121.52, 124.43, 126.04, 126.22, 128.82, 129.25,
129.52, 133.41, 133.85, 134.35, 134.71, 138.42, 149.73, 150.72,
151.92, 169.92, 170.04. MS, m/z: [Mþ1]þ 471.20. Anal. calcd.
for C27H26N4O4: C, 68.92; H, 5.57; N, 11.91. Found C, 68.95;
H, 5.59; N, 11.89.
2-(3,4,5-Trimethoxystyryl)-4-(4-methoxyphenyl ureido)-
quinazoline (7i)
Yield (73%), mp 193–1958C; IR (KBr) (cmꢀ1): 1731 (C C str. a,
–
–
b unsat.), 1621 (C N str.), 1582 (C O str. in urea), 3340 (–NH
–
–
–
–
str.), 1542 (–NH def.), 813 (C–O–C assym.), 1242 (C–O–C sym.);
1H NMR (300 MHz; DMSO-d6; d ppm): 3.74 (s, 3H, –OCH3), 3.88 (s,
–
6H, 2x–OCH ), 6.56 (d, 1H, J ¼ 15, –CH CH), 8.02 (d, 1H, J ¼ 16,
–
3
–
–
–CH CH), 8.86 (s, 1H, –NH), 9.42 (s, 1H, –NH), 6.61 (d, 2H, J ¼ 7,
2-(3,4,5-Trimethoxystyryl)-4-(3-methyl phenyl ureido)-
quinazoline (7f)
aromatic), 6.68 (dd, 1H, J ¼ 7.0, 2.2, Ar–H), 6.74 (dd, 1H, J ¼ 8.27,
2.34, Ar–H), 7.22–7.84 (m, 6H, Ar–H), 3.74 (s, 3H, Ar–OCH3). 13C NMR
(75 MHz; DMSO-d6; d ppm): 55.80, 56.10, 56.42, 103.84, 112.74,
114.50, 115.62, 119.72, 122.63, 126.22, 128.12, 128.80, 129.52,
133.40, 133.82, 138.42, 149.70, 150.72, 151.90, 156.22, 169.90,
170.05. MS, m/z: [Mþ1]þ 486.19. Anal. calcd. for C27H26N4O5: C,
66.65; H, 5.39; N, 11.52. Found C, 66.59; H, 5.41; N, 11.49.
Yield (64%), mp 188–1908C; IR (KBr) (cmꢀ1): 1731 (C C str. a, b
–
–
unsat.), 1620 (C N str.), 1583 (C O str. in urea), 3343 (–NH str.),
–
–
–
–
1545 (–NH def.), 810 (C–O–C assym.), 1240 (C–O–C sym.), 1394
(C–CH3 str. in aromatic ring); 1H NMR (300 MHz; DMSO-d6;
d ppm): 2.42 (s, 3H, Ar–CH3), 3.76 (s, 3H, –OCH3), 3.86 (s,
–
6H, 2x–OCH ), 6.55 (d, 1H, J ¼ 15, –CH CH), 8.04 (d, 1H,
–
3
–
–
J ¼ 16, –CH CH), 8.84 (s, 1H, –NH), 9.41 (s, 1H, –NH), 6.63 (d,
2-(3,4,5-Trimethoxystyryl)-4-(3-nitrophenyl ureido)-
quinazoline (7j)
2H, J ¼ 7, aromatic), 6.66 (dd, 1H, J ¼ 7.45, 2.34, Ar–H), 6.77 (dd,
1H, J ¼ 8.39, 2.19, Ar–H), 7.22–7.84 (m, 6H, Ar–H). 13C NMR
(75 MHz; DMSO-d6; d ppm): 24.32, 56.15, 56.43, 103.82, 112.72,
115.60, 118.62, 119.73, 121.32, 124.63, 126.22, 128.82, 128.94,
129.55, 133.43, 133.82, 135.72, 138.46, 138.63, 149.72, 150.74,
151.94, 169.92, 170.02. MS, m/z: [Mþ1]þ 471.20. Anal. calcd.
for C27H26N4O4: C, 68.92; H, 5.57; N, 11.91. Found C, 68.85;
H, 5.54; N, 11.87.
Yield (62%), mp 164–1668C; IR (KBr) (cmꢀ1): 1732 (C C str. a,
–
–
b unsat.), 1620 (C N str.), 1578 (C O str. in urea), 3342 (–NH str.),
–
–
–
–
1545 (–NH def.), 810 (C–O–C assym.), 1240 (C–O–C sym.), 1546
(C–NO2 str. in aromatic ring); 1H NMR (300 MHz; DMSO-d6;
d ppm): 3.73 (s, 3H, –OCH3), 3.87 (s, 6H, 2x–OCH3), 6.55 (d, 1H,
–
–
J ¼ 15, –CH CH), 8.03 (d, 1H, J ¼ 16, –CH CH), 8.85 (s, 1H, –NH),
–
–
9.44 (s, 1H, –NH), 6.63 (d, 2H, J ¼ 7, aromatic), 6.67 (dd, 1H,
J ¼ 7.59, 2.49, Ar–H), 6.75 (dd, 1H, J ¼ 8.43, 2.36, Ar–H),
7.22–7.84 (m, 6H, Ar–H). 13C NMR (75 MHz; DMSO-d6; d ppm):
56.12, 56.40, 103.82, 112.72, 114.54, 115.63, 119.53, 119.72,
126.22, 127.73, 128.86, 129.55, 129.94, 133.42, 133.82, 136.72,
138.42, 148.14, 149.74, 150.72, 151.93, 169.92, 170.02. MS,
m/z: [Mþ1]þ 502.16. Anal. calcd. for C26H23N5O6: C, 62.27;
H, 4.62; N, 13.97. Found C, 62.20; H, 4.60; N, 13.91.
2-(3,4,5-Trimethoxystyryl)-4-(4-methyl phenyl ureido)-
quinazoline (7g)
Yield (70%), mp 172–1758C; IR (KBr) (cmꢀ1): 1734 (C C str. a, b
–
–
unsat.), 1623 (C N str.), 1579 (C O str. in urea), 3341 (–NH str.),
–
–
–
1543 (–NH def.), 812 (C–O–C assym.), 1241 (C–O–C sym.), 1388
–
(C–CH3 str. in aromatic ring); 1H NMR (300 MHz; DMSO-d6;
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