S.K. Kashaw et al. / European Journal of Medicinal Chemistry 44 (2009) 4335–4343
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(m, 2H, –CH2), 0.9 (m, 3H, –CH3 present at C2 of 4(3H)-quinazoli-
none ring), 6.0 (s, 2H of –NH–CO–NH–); MI m/z peak at 323.
Compound E10: 1-(2-ethyl-4-oxo-4H-quinazolin-3-yl)-3-(4-
ethyl-phenyl)-urea; IR (cmꢁ1): 1696 (C]O str. of 4(3H)-quinazoli-
none ring), 1668 (C]O str. of phenyl urea), 1580 (C]N), 3041
(Ar–CH str.), 3422 (secondary amide NH str.), 2970 (C–H str.); 13C
Compound P3: 1-(4-chloro-phenyl)-3-(4-oxo-2-phenyl-4H-
quinazolin-3-yl)-urea; IR (cmꢁ1): 1683 (C]O str. of 4(3H)-quina-
zolinone ring), 1669 (C]O str. of phenyl urea), 1582 (C]N), 3045
(Ar–CH str.), 3420 (secondary amide NH str.), 2970 (C–H str.); 13C
NMR (300 MHz, d): 165 (C-4), 164 (C-2), 121.1 (C8 of 4(3H)-quina-
zolinone ring), 125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of
4(3H)-quinazolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring),
154.3 (CZ of phenyl urea), 133 (C01), 129.4 (C04), 136.3 (C001), 129.9
NMR (300 MHz, d): 165 (C-4), 164 (C-2), 109 (C-11), 121.1 (C8 of
4(3H)-quinazolinone ring), 21.7 (Ca), 5.3 (Cb), 28.6 (Cc), 16.1 (Cd),
125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of 4(3H)-quina-
zolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring), 154 (CZ of
(C004); 1H NMR (300 MHz,
d): 7.4–7.9 (m, 4H, Ar–H of (3H)-quina-
zolinone ring), 7.0–7.64 (m, 4H, Ar–H of phenyl urea), 7.29–7.62 (m,
5H, Ar–H of phenyl ring at C2), 6.0 (s, 2H of –NH–CO–NH–); MI m/z
peak at 391.
Compound P4: 1-(4-bromo-phenyl)-3-(4-oxo-2-phenyl-4H-
quinazolin-3-yl)-urea; IR (cmꢁ1): 1698 (C]O str. of 4(3H)-quina-
zolinone ring), 1660 (C]O str. of phenyl urea), 1584 (C]N), 3045
(Ar–CH str.), 3420 (secondary amide NH str.), 2970 (C–H str.); 13C
phenyl urea), 133 (C04); 1H NMR (300 MHz,
d): 7.4–7.9 (m, 4H, Ar–H
of (3H)-quinazolinone ring), 6.88–7.52 (m, 4H, Ar–H of phenyl
urea), 1.24–2.59 (m, 5H, –CH2CH3), 1.4 (m, 2H, –CH2), 0.9 (m, 3H,
–CH3 present at C2 of 4(3H)-quinazolinone ring), 6.0 (s, 2H of –NH–
CO–NH–); MI m/z peak at 337.
Compound E11: 1-(2-ethyl-4-oxo-4H-quinazolin-3-yl)-3-(4-
methoxy-phenyl)-urea; IR (cmꢁ1): 1686 (C]O str. of 4(3H)-qui-
nazolinone ring), 1670 (C]O str. of phenyl urea), 1590 (C]N),
3042 (Ar–CH str.), 3423 (secondary amide NH str.), 2970 (C–H
NMR (300 MHz, d): 165 (C-4), 164 (C-2), 121.1 (C8 of 4(3H)-quina-
zolinone ring), 125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of
4(3H)-quinazolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring),
154 (CZ of phenyl urea), 137.2 (C01), 118.7 (C04), 132.9 (C001), 129.9
str.); 13C NMR (300 MHz,
d): 165 (C-4), 164 (C-2), 109 (C-11),
121.15(C8 of 4(3H)-quinazolinone ring), 21.7 (Ca), 5.3 (Cb), 56.0
(Cc), 125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of 4(3H)-
quinazolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring), 154
(C004); 1H NMR (300 MHz,
d): 7.4–7.9 (m, 4H, Ar–H of (3H)-quina-
zolinone ring), 7.0–7.64 (m, 4H, Ar–H of phenyl urea), 7.29–7.62 (m,
5H, Ar–H of phenyl ring at C2), 6.0 (s, 2H of –NH–CO–NH–); MI m/z
peak at 436.
(CZ of phenyl urea), 157 (C04); 1H NMR (300 MHz,
d): 7.4–7.9 (m,
4H, Ar–H of (3H)-quinazolinone ring), 6.74–7.53 (m, 4H, Ar–H of
phenyl urea), 3.73 (s, 3H, –CH3), 1.4 (m, 2H, –CH2), 0.9 (m, 3H,
–CH3 present at C2 of 4(3H)-quinazolinone ring), 6.0 (s, 2H of
–NH–CO–NH–); MI m/z peak at 339.
Compound P5: 1-(4-iodo-phenyl)-3-(4-oxo-2-phenyl-4H-qui-
nazolin-3-yl)-urea; IR (cmꢁ1): 1697 (C]O str. of 4(3H)-quinazoli-
none ring), 1668 (C]O str. of phenyl urea), 1578 (C]N), 3045 (Ar–
CH str.), 3420 (secondary amide NH str.), 2970 (C–H str.); 13C NMR
Compound E12: 1-(4-ethoxy-phenyl)-3-(2-ethyl-4-oxo-4H-
quinazolin-3-yl)-urea; IR (cmꢁ1): 1680 (C]O str. of 4(3H)-quina-
zolinone ring), 1665 (C]O str. of phenyl urea), 1582 (C]N), 3045
(Ar–CH str.), 3420 (secondary amide NH str.), 2970 (C–H str.); 13C
(300 MHz, d): 165 (C-4), 164 (C-2), 121.1 (C8 of 4(3H)-quinazolinone
ring), 125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of 4(3H)-
quinazolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring), 154 (CZ
of phenyl urea), 137.1 (C01), 92.9 (C04), 132.9 (C001), 129.9 (C004); 1H
NMR (300 MHz,
d
): 165 (C-4), 164 (C-2), 109 (C-11), 121.1 (C8 of
NMR (300 MHz, d): 7.4–7.9 (m, 4H, Ar–H of (3H)-quinazolinone
4(3H)-quinazolinone ring), 21.7 (Ca), 5.3 (Cb), 65.1 (Cc), 14.3 (Cd),
125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of 4(3H)-quina-
zolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring), 154 (CZ of
ring), 7.0–7.64 (m, 4H, Ar–H of phenyl urea), 7.29–7.62 (m, 5H, Ar–H
of phenyl ring at C2), 6.0 (s, 2H of –NH–CO–NH–); MI m/z peak at
383.
Compound P6: 1-(4-nitro-phenyl)-3-(4-oxo-2-phenyl-4H-qui-
nazolin-3-yl)-urea; IR (cmꢁ1): 1681 (C]O str. of 4(3H)-quinazoli-
none ring), 1666 (C]O str. of phenyl urea), 1586 (C]N), 3045
(Ar–CH str.), 3420 (secondary amide NH str.), 2970 (C–H str.); 13C
phenyl urea), 157 (C04); 1H NMR (300 MHz,
d): 7.4–7.9 (m, 4H, Ar–H
of (3H)-quinazolinone ring), 6.75–7.53 (m, 4H, Ar–H of phenyl
urea), 1.33–3.98 (m, 5H, –CH2CH3), 1.4 (m, 2H, –CH2), 0.9 (m, 3H,
–CH3 present at C2 of 4(3H)-quinazolinone ring), 6.0 (s, 2H of –NH–
CO–NH–); MI m/z peak at 353.
NMR (300 MHz, d): 165 (C-4), 164 (C-2), 121.1 (C8 of 4(3H)-quina-
Compound
P1:
1-(4-oxo-2-phenyl-4H-quinazolin-3-yl)-3-
zolinone ring), 125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of
4(3H)-quinazolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring),
154 (CZ of phenyl urea), 144.3 (C01), 144.0 (C04), 132.9 (C001), 129.9
phenyl urea; IR (cmꢁ1): 1682 (C]O str. of 4(3H)-quinazolinone
ring), 1672 (C]O str. of phenyl urea), 1598 (C]N), 3045 (Ar–CH
str.), 3420 (secondary amide NH str.), 2970 (C–H str.); 13C NMR
(C004); 1H NMR (300 MHz,
d): 7.4–7.9 (m, 4H, Ar–H of (3H)-quina-
(300 MHz,
d
): 165 (C-4), 164 (C-2), 121.1 (C8 of 4(3H)-quinazolinone
zolinone ring), 7.0–7.64 (m, 4H, Ar–H of phenyl urea), 7.29–7.62 (m,
5H, Ar–H of phenyl ring at C2), 6.0 (s, 2H of –NH–CO–NH–); MI m/z
peak at 402.
Compound P7: 1-(4-oxo-2-phenyl-4H-quinazolin-3-yl)-3-o-
tolyl urea; IR (cmꢁ1): 1689 (C]O str. of 4(3H)-quinazolinone ring),
1665 (C]O str. of phenyl urea), 1588 (C]N), 3045 (Ar–CH str.),
3420 (secondary amide NH str.), 2970 (C–H str.); 13C NMR
ring), 125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of 4(3H)-
quinazolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring), 154.3
(CZ of phenyl urea), 138.2 (C01), 124.1 (C04), 132.9 (C001), 129.9 (C004);
1H NMR (300 MHz,
d): 7.4–7.9 (m, 4H, Ar–H of (3H)-quinazolinone
ring), 7.0–7.64 (m, 5H, Ar–H of phenyl urea), 7.29–7.62 (m, 5H, Ar–H
of phenyl ring at C2), 6.0 (s, 2H of –NH–CO–NH–); MI m/z peak at
357.
(300 MHz, d): 165 (C-4), 164 (C-2), 121.1 (C8 of 4(3H)-quinazolinone
Compound P2: 1-(4-fluoro-phenyl)-3-(4-oxo-2-phenyl-4H-
quinazolin-3-yl)-urea; IR (cmꢁ1): 1698 (C]O str. of 4(3H)-quina-
zolinone ring), 1656 (C]O str. of phenyl urea), 1581 (C]N), 3045
(Ar–CH str.), 3420 (secondary amide NH str.), 2970 (C–H str.); 13C
ring), 125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of 4(3H)-
quinazolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring), 154 (CZ
of phenyl urea), 138 (C01), 129.6 (C02), 124.0 (C04), 11.8 (Ca), 132.9
(C001), 129.9 (C004); 1H NMR (300 MHz,
d): 7.4–7.9 (m, 4H, Ar–H of
NMR (300 MHz,
d
): 165 (C-4), 164 (C-2), 121.1 (C8 of 4(3H)-quina-
(3H)-quinazolinone ring), 7.0–7.64 (m, 5H, Ar–H of phenyl urea),
7.29–7.62 (m, 4H, Ar–H of phenyl ring at C2), 6.0 (s, 2H of –NH–CO–
NH–); MI m/z peak at 371.
Compound P8: 1-(4-oxo-2-phenyl-4H-quinazolin-3-yl)-3-m-
tolyl urea; IR (cmꢁ1): 1679 (C]O str. of 4(3H)-quinazolinone ring),
1664 (C]O str. of phenyl urea), 1592 (C]N), 3045 (Ar–CH str.),
3420 (secondary amide NH str.), 2970 (C–H str.); 13C NMR
zolinone ring), 125.9 (C10 of 4(3H)-quinazolinone ring), 126.1 (C6 of
4(3H)-quinazolinone ring), 146.8 (C9 of 4(3H)-quinazolinone ring),
154.3 (CZ of phenyl urea), 133 (C01), 157.7 (C04), 132.9 (C001), 129.9
(C004); 1H NMR (300 MHz,
d): 7.4–7.9 (m, 4H, Ar–H of (3H)-quina-
zolinone ring), 7.0–7.64 (m, 4H, Ar–H of phenyl urea), 7.29–7.62 (m,
5H, Ar–H of phenyl ring at C2), 6.0 (s, 2H of –NH–CO–NH–); MI m/z
peak at 375.
(300 MHz, d): 165 (C-4), 164 (C-2), 121.1 (C8 of 4(3H)-quinazolinone