410 El-Sayed et al.
Arch. Pharm. Pharm. Med. Chem. 2002, 335, 403–410
Table 4. (continued)
Comp
No.
R
Yield
[%]
Mp
[°C]
Mol. formula
(Mol. wt.)
1H-NMR
(DMSO-d6)
7 f
OCH3
50
271–273
C16H11N3O2
(277.28)
3.68 (s, 3 H, OCH3 overlapping with DMSO, 6.82–7.70 (m,
4 H, C1,2,3,4-H), 7.74 (d, J = 8.8 Hz, 1 H, C9-H), 7.78 (d, J
= 8.8 Hz, 1 H, C8-H), 8.44 (s, 1 H, C11-H), 8.66 (s, 1 H,
C7-H)
a The yield is calculated according to Method B.
ed solid was filtered and crystallized from dimethylformamide/
ethanol (1 : 2) to obtain the products 7 a–c and 7 d–f as the
monohydrochlorides. These were treated with 10 N NaOH
(5–10 mL) to give the free bases.IR (cm–1):1666–1660 (C=O).
13C-NMR for 9-methoxythiazolo[3Ј,2Ј:1,2]pyrimido[4,5-b]-
quinolin-5-one 7 c: 166.2 (C5), 160.0 (C3a), 155.5 (C11a), 140.5
(C9), 137.1 (C1), 134.0 (C10a), 130.5 (C5a), 126.6 (C6), 122.0
(C6a), 114.0 (C7), 112.7 (C10), 111.0 (C8), 102.6 (C2), 55.1
(OCH3). 13C-NMR for pyrido [1Ј,2Ј:1,2]pyrimido[4,5-b]quinolin-
6-one 7 d: 163.7 (C6), 158.6 (C4a), 155.2 (C12a), 149.0 (C1),
147.9 (C11a), 142.5 (C6a), 138.0 (C7), 137.6 (C7a), 137.2 (C11),
130.1 (C10), 127.8 (C8), 125.0 (C9), 122.3 (C3), 118.1 (C4),
115.3 (C2). M.S. for thiazolo[3Ј,2Ј:1,2]pyrimido[4,5-b]quinolin-
5-one 7 a m/z %:253 (56 %).229 (10 %), 212 (7 %), 196 (26 %),
186 (100 %), 170 (7 %), 153 (59 %), 142 (18 %), 128 (18 %),
114 (19 %), 100 (12 %), 76 (19 %), 64 (75 %). Physical and
spectral data of the products are recorded in Table 4.
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The microdilution susceptibility test in Muller-Hinton Broth (Ox-
oid) and Sabouraud Liquid Medium (Oxoid) were used for the
determination of antibacterial and antifungal activities [13].
Test organisms included:Staphylococcus aureus ATCC 29213,
Bacillus subtilis ATCC 6633, Bacillus sphaericus; Institute Pas-
teur, Bacillus thuringiensis ATCC 1322, and Bacillus anthracis
as Gram-positive bacteria, Salmonella typhimurium ATCC
3311, Escherichia coli ATCC 25722, and Esherichia coli ATCC
13607 as Gram-negative bacteria, Aspergillus flavus local, as
fungi, and Candida albicans ATCC 10231 as yeast-like fungi.
Ampicillin trihydrate and clotrimazole were used as standard
antibacterial and antifungal agents respectively. Solutions of
the tested compounds, ampicillin trihydrate and clotrimazole,
were prepared in dimethylformamide at a concentration of
1 mg /mL. Two-fold dilution of the compounds was performed.
Plates were incubated at 37 °C for 24 h for bacteria and
48–72 h for fungi. The MICs of all the tested compounds were
determined by means of standard two-fold serial dilution meth-
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