Med Chem Res
3-(4-(2-(4-methoxyphenyl)-4-oxothiazolidin-3yl)phenyl)-2-
phenylquinazolin-4(3H)-one (QT5)
2′′, H-6′′, H-5), 10.1 (1H, s, OH); 13C NMR (DMSO-d6) δ
= 171.2 (N–CO–C), 165.4 (N=C–N), 161.4 (N–CO–C),
156.9 (C–OH), 151.3 (C–N), 137.6 (C–N), 133.1 (C-7),
131.8 (C-1‴), 130.2 (C-2‴), 130.2 (C-6‴), 130.1 (C-4′),
129.8 (C-2′,C-6′), 128.8 (C-3′, C-5′),128.7 (C-5, C-1′),
128.4 (C–N), 127.7 (C-6), 122.4 (C-8), 121.3 (C-2″, C-3″,
C-5″, C-6″), 120.6 (C-10), 115.8 (C-3‴), 115.8 (C-5‴), 65.1
(N-C-S), 33.5 (CH2); MS: m/z = 491.13; Anal. Calcd for:
C29H21N3O3S: C, 70.86; H, 4.31; N, 8.55%. Found C,
70.82; H, 4.27; N, 8.51%.
Yield 59.41%; mp > 300 °C; IR (KBR) vmax 3060.01(CH
aromatic), 1715.10 (C=O), 1607.49 (C=N), 1305.12
(C–N), 1280–1253 (C–O–C);1H NMR (300 MHz, DMSO-
d6) δ = 3.40 (1H, dd, H-IIIb), 3.48 (1H, dd, H-IIIa), 3.73
(3H,s, OCH3), 5.97 (1H, s, H-V), 6.65 (2H, dd, H-3′′′,
H-5′′′), 6.95 (2H, dd, H-2′′′, H-6′′′), 7.10–7.15 (2H, m,
H-3′′, H-5′′), 7.32–7.45 (6H, m, H-6 to H-8, H-3′ to H-5′),
7.63–7.92 (5H, m, H-2′, H-6′, H-2′′, H-6′′, H-5);13C NMR
(DMSO-d6) δ = 171.7 (N–CO–C), 165.1 (N=C–N), 161.2
(N–CO–C), 159.1 (C-OCH3), 151.7 (C–N), 137.4 (C–N),
133.1 (C-7), 131.5 (C-1‴), 130.1 (C-4′), 129.8 (C-2‴),
129.8 (C-6‴), 129.3 (C-2′, C-6′), 128.9 (C-3′, C-5′), 128.8
(C-1′, C-5), 128.6 (C–N), 127.7 (C-6), 122.5 (C-8), 121.2
(C-2″), 121.1 (C-3″, C-5″, C-6″), 120.5 (C-10), 114.2 (C-
5‴), 114.2 (C-3‴),65.6 (N–C–S), 55.9 (CH3), 33.5 (CH2);
MS: m/z = 505.15; Anal. Calcd for: C30H23N3O3S: C,
71.27; H, 4.59; N, 8.37%. Found C, 71.22; H, 4.53; N,
8.33%.
3-(4-(4-oxo-2-p-tolylthiazolidin-3yl)phenyl)-2-
phenylquinazolin-4(3H)-one (QT8)
Yield 57.2%; mp > 300 °C; IR (KBR) vmax 3060.34 (CH
aromatic), 1721.08 (C=O), 1601.32 (C=N), 1306.79
1
(C–N); H NMR (300 MHz, DMSO-d6) δ = 2.35 (3H, s,
CH3), 3.48 (1H, dd, H-IIIb), 3.51 (1H, dd, H-IIIa), 5.89 (1H,
s, H-V), 6.94–7.01 (4H, m, H-2′′′, H-3′′′ H-5′′′, H-6′′′),
7.05–7.12 (2H, m, H-3′′, H-5′′), 7.26–7.50 (6H, m, H-6 to
H-8, H-3′ to H-5′), 7.61–7.88 (5H, m, H-2′, H-6′, H-2′′,
H-6′′, H-5); 13C NMR (DMSO-d6) δ = 172.1 (N-CO-C),
165.6 (N=C–N), 161.3 (N–CO–C), 151.6 (C–N), 137.3
(C–N), 136.8 (C-4‴), 136.2 (C-1‴), 133.5 (C-7), 131.1 (C-
4′), 130.0 (C-2′, C-6′), 129.2 (C-3′, C-5′), 129.0 (C-3‴, C-
5‴), 128.9 (C-1′), 128.8 (C-5), 128.7 (C-6‴, C-2‴), 128.5
(C–N), 127.3 (C-6), 122.6 (C-8), 121.8 (C-2″, C-3″, C-5″,
C-6″), 120.5 (C-10), 65.1 (N–C–S), 33.5 (CH2), 24.3 (CH3);
MS: m/z = 489.15; Anal. Calcd for: C30H23N3O2S: C,
73.60; H, 4.74; N, 8.58%. Found C, 73.52; H, 4.69; N,
8.52%.
3-(4-(2-(3-methoxyphenyl)-4-oxothiazolidin-3yl)phenyl)-2-
phenylquinazolin-4(3H)-one (QT6)
Yield 62.5%; mp > 300 °C; IR (KBR) vmax 3063.29 (CH
aromatic), 1721.12 (C=O), 1604.68 (C=N), 1323.75 (C–N)
1
1250 (C–O–C); H NMR (300 MHz, DMSO-d6) δ = 3.46
(1H, dd, H-IIIb), 3.50 (1H, dd, H-IIIa), 3.76 (3H,s, OCH3),
5.97 (1H, s, H-V), 6.57–6.62 (3H, m, H-2′′′, H-4′′′, H-6′′′),
7.03–7.08 (3H, m, H-5′′′,H-3′′, H-5′′), 7.28–7.51 (6H, m, H-
6 to H-8, H-3′ to H-5′), 7.62–7.89 (5H, m, H-2′, H-6′, H-2′′,
H-6′′, H-5); 13C NMR (DMSO-d6) δ = 171.5 (N–CO–C),
165.2 (N=C–N), 161.3 (N–CO–C), 160.6 (C–OCH3),
151.5 (C–N), 140.2 (C-1‴), 137.6 (C–N), 133.2 (C-7),
131.2 (C-4′), 129.9 (C-2′, C-6′), 129.7 (C-5‴), 129.0 (C-3′,
C-5′), 128.9 (C-5), 128.7 (C-1′), 128.5 (C–N), 127.3 (C-6),
122.7 (C-8), 121.4 (C-2″, C-3″, C-5″, C-6″), 121.1 (C-
6‴),120.5 (C-10), 112.8 (C-2‴), 112.7 (C-4‴), 65.9
(N–C–S), 55.8 (CH3), 33.6 (CH2); MS: m/z = 505.15; Anal.
Calcd for: C30H23N3O3S: C, 71.25; H, 4.61; N, 8.31%.
Found C, 71.20; H, 4.55; N, 8.29%.
3-(4-(2-(4-fluorophenyl)-4-oxothiazolidin-3yl)phenyl)-2-
phenylquinazolin-4(3H)-one (QT9)
Yield 53%; mp > 300 °C; IR (KBR) vmax 3061.36 (CH
aromatic), 1713.93 (C=O), 1603.02 (C=N), 1307.22
1
(C–N), 1235 (C–F); H NMR (300 MHz, DMSO-d6) δ =
3.39 (1H, dd, H-IIIb), 3.46(1H, dd, H-IIIa), 5.93 (1H, s, H-
V), 6.85 (2H, dd, H-3′′′, H-5′′′), 7.04 (2H, dd, H-2′′′, H-6′′′),
7.10–7.16 (2H, m, H-3′′, H-5′′), 7.39–7.50 (6H, m, H-6 to
H-8, H-3′ to H-5′), 7.65–7.93 (5H, m, H-2′, H-6′, H-2′′, H-6′
′, H-5); 13C NMR (DMSO-d6) δ = 171.8 (N–CO–C), 165.3
(N=C–N), 161.6 (N–CO–C), 161.3 (C–F), 151.5 (C–N),
137.6 (C–N), 134.8 (C-1‴), 133.8 (C-7), 131.0 (C-4′), 130.4
(C-2‴, C-6‴), 130.2 (C-2′, C-6′), 129.1 (C-3′, C-5′), 128.7
(C-5, C-1′), 128.6 (C–N), 127.5 (C-6), 122.2 (C-8), 121.3
(C-2″, C-3″, C-5″, C-6″), 120.7 (C-10), 115.4 (C-3‴), 115.4
(C-3‴), 65.1 (N–C–S), 33.5 (CH2); MS: m/z = 493.15;
Anal, Calcd for: C29H20FN3O2S: C, 70.57; H, 4.08; N,
8.51%. Found C, 70.51; H, 4.01; N, 8.47%.
3-(4-(2-(4-hydroxyphenyl)-4-oxothiazolidin-3yl)phenyl)-2-
phenylquinazolin-4(3H)-one (QT7)
Yield 54.32%; mp > 300 °C; IR (KBR) vmax 3470–3320
(O–H), 3064.42 (CH aromatic), 1724.21 (C=O), 1602.62
(C=N), 1327.40 (C–N); 1H NMR (300 MHz, DMSO-d6) δ
= 3.42 (1H, dd, H-IIIb), 3.49 (1H, dd, H-IIIa), 5.94 (1H, s,
H-V), 6.61 (2H, dd, H-3′′′, H-5′′′), 6.89 (2H, dd, H-2′′′,
H-6′′′), 7.08–7.15 (2H, m, H-3′′, H-5′′), 7.30–7.46 (6H, m,
H-6 to H-8, H-3′ to H-5′), 7.69–7.90 (5H, m, H-2′, H-6′, H-