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Med Chem Res (2013) 22:225–233
1-(4-Methylsulfanyl-phenyl)-3-[2-(6-nitro-4-oxo-2-phenyl-
4H-quinazolin-3-yl)-ethyl]-urea (7j)
145.21 (C=N, quinazolinone ring), 142.44 (C–NO2),
141.99, 138.65, 134.29, 134.53, 133.32, 133.38, 129.96,
129.73, 129.22, 128.10, 127.82, 127.72, 127.24, 125.92,
125.53, 122.25, 121.77, 40.59 (–CH2), 39.25 (–CH2), 11.89
(–CH3); IR (KBR, cm-1): 3303.59 (–NH), 1691.0 (C=O
str.), 1538.20 (C=N str.), 1507.09 (–NO2 asy.), 1336.36
(–NO2 sym.), 1158 (C–N str.); ESI–MS (m/z): 444 (M?1).
1H NMR (400 MHz, DMSO, dppm): 8.94 (1H, s, –NH), 6.77
(1H, t, –NH), 6.92–8.71 (12H, m, Ar–H), 2.32 (3H, s, –CH3),
2.47 (2H, q, –CH2), 1.20 (2H, t, –CH2); 13C NMR (100 MHz,
DMSO, dppm): 166.51 (C=O), 165.83 (C=O), 145.23 (C=N,
quinazolinone ring), 142.37 (C–NO2), 141.91, 138.56,
134.92, 134.35, 133.39, 133.30, 129.76, 129.73, 129.46,
128.15, 127.97, 127.92, 127.84, 125.54, 1258.43, 122.25,
121.77, 40.62 (–CH2), 39.37 (–CH2), 16.70 (–SCH3); IR
(KBR, cm-1): 3303.59 (–NH), 1691.0 (C=O str.), 1538.20
(C=N str.), 1507.09 (–NO2 asy.), 1336.36 (–NO2 sym.), 1158
(C–N str.); ESI–MS (m/z): 476 (M?1).
1-[2-(6-Nitro-4-oxo-2-phenyl-4H-quinazolin-3-yl)-ethyl]-
3-p-tolyl-urea (7g)
1H NMR (400 MHz, DMSO, dppm): 8.96 (1H, s, –NH),
6.91 (1H, t, –NH), 7.34–8.89 (12H, m, Ar–H), 2.32 (2H, q,
–CH2), 2.25 (3H, s, –CH3), 1.29 (2H, t, –CH2); 13C NMR
(100 MHz, DMSO, dppm): 166.51 (C=O), 165.89 (C=O),
145.29 (C=N, quinazolinone ring), 142.54 (C–NO2),
141.89, 138.55, 134.23, 134.53, 133.52, 133.38, 129.92,
129.63, 129.32, 128.11, 127.93, 12.63, 127.36, 125.83,
125.59, 122.76, 121.77, 40.54 (–CH2), 39.29 (–CH2), 11.97
(–CH3); IR (KBR, cm-1): 3303.59 (–NH), 1691.0 (C=O
str.), 1538.20 (C=N str.), 1507.09 (–NO2 asy.), 1336.36
(–NO2 sym.), 1158 (C–N str.); ESI–MS (m/z): 444 (M?1).
1-(2-Chloro-5-trifluoromethyl-phenyl)-3-[2-(6-nitro-4-oxo-
2-phenyl-4H-quinazolin-3-yl)-ethyl]-urea (7k)
1H NMR (400 MHz, DMSO, dppm): 8.95 (1H, s, –NH),
6.84 (1H, t, –NH), 7.04–8.72 (11H, m, Ar–H), 2.44 (2H, q,
–CH2), 1.21 (2H, t, –CH2); 13C NMR (100 MHz, DMSO,
dppm): 166.35 (C=O), 165.76 (C=O), 145.21 (C=N, qui-
nazolinone ring), 142.35 (C–NO2), 141.39, 134.31, 133.35,
133.35, 130.32 (C–Cl), 129.73, 129.77, 129.41, 128.19,
127.97, 127.82, 127.44, 125.58, 125.43, 123.15, 122.20,
121.71, 119.23 (–CF3), 40.58 (–CH2), 39.32 (–CH2); IR
(KBR, cm-1): 3303.59 (–NH), 1691.0 (C=O str.), 1538.20
(C=N str.), 1507.09 (–NO2 asy.), 1336.36 (–NO2 sym.),
1158 (C–N str.); ESI–MS (m/z): 533 (M?1).
1-[2-(6-Nitro-4-oxo-2-phenyl-4H-quinazolin-3-yl)-ethyl]-
3-(4-trifluoromethyl-phenyl)-urea (7h)
1H NMR (400 MHz, DMSO, dppm): 8.99 (1H, s, –NH),
6.91 (1H, t, –NH), 7.15–8.81 (12H, m, Ar–H), 2.49 (2H, q,
–CH2), 1.26 (2H, t, –CH2); 13C NMR (100 MHz, DMSO,
dppm): 166.35 (C=O), 165.76 (C=O), 145.21 (C=N, qui-
nazolinone ring), 142.35 (C–NO2), 141.39, 134.31, 133.35,
133.35, 130.32, 129.73, 129.77, 129.41, 128.19, 127.97,
127.82, 127.44, 125.58, 125.43, 123.15, 122.20, 121.71,
119.23 (–CF3), 40.58 (–CH2), 39.32 (–CH2); IR (KBR,
cm-1): 3303.59 (–NH), 1691.0 (C=O str.), 1538.20 (C=N
str.), 1507.09 (–NO2 asy.), 1336.36 (–NO2 sym.), 1283.92
(C–F str.), 1158 (C–N str.); ESI–MS (m/z): 498 (M?1).
Pharmacology
The newly synthesized compounds 7 (a–k) were evaluated
for their in vitro antibacterial and antifungal activities. The
standard strain used for antimicrobial activity was procured
from Promotech Life sciences, Bangalore. The in vitro
antibacterial activity were performed against gram-positive
bacteria B. subtilis ATCC 11774 and S. aureus ATCC
25923 and gram-negative bacteria E. coli ATCC 25922 and
P. aeruginosa ATCC 27853 by using Kirby Bauer tech-
nique and serial broth dilution technique. Here, antifungal
screening was carried out by using C. albicans ATCC
66027 by the same method.
1-(3,5-Bis-trifluoromethyl-phenyl)-3-[2-(6-nitro-4-oxo-
2-phenyl-4H-quinazolin-3-yl)-ethyl]-urea (7i)
1H NMR (400 MHz, DMSO, dppm): 8.96 (1H, s, –NH),
6.90 (1H, t, –NH), 7.09–8.45 (11H, m, Ar–H), 2.48 (2H, q,
–CH2), 1.27 (2H, t, –CH2); 13C NMR (100 MHz, DMSO,
dppm): 166.47 (C=O), 165.47 (C=O), 145.25 (C=N, qui-
nazolinone ring), 142.39 (C–NO2), 141.41, 134.33, 133.37,
133.45, 130.49, 129.77, 129.71, 129.41, 128.21, 127.99,
127.78, 127.41, 125.59, 125.49, 123.51, 122.27, 121.79,
119.87 (–CF3), 119.23 (–CF3), 40.58 (–CH2), 39.32
(–CH2); IR (KBR, cm-1): 3303.59 (–NH), 1691.0 (C=O
str.), 1538.20 (C=N str.), 1507.09 (–NO2 asy.), 1336.36
(–NO2 sym.), 1283.92 (C–F str.), 1158 (C–N str.); ESI–MS
(m/z): 566 (M?1).
Kirby Bauer is a technique which uses antibiotic
impregnated wafers to test whether particular bacteria are
susceptible to specific antibiotics. First, the Mueller–Hinton
agar media were sterilized (autoclaved at 120°C for half an
hour), poured into a Petri dish maintaining uniform depth of
5 mm and allowed to solidify. The microbial suspension
(105 CFU/ml) (0.5 McFarland Nephelometery Standards)
was streaked over the surface of agar using a sterile cotton
swab for growth of the organisms. Here, all the compounds
7(a–k) were dissolved in dimethyl sulfoxide and seven
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