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IR spectrum, ν, cm–1: 3100 (O–H), 1606 (C=N), 1456
(C=C), 1225 (C–O), 746 (C–S), 559 (S–S). H NMR
6.48–6.59 m (2H, Ar-H), 7.13 d.d (1H, J = 7.7, 1.2 Hz,
Ar-H), 7.17 d.d (1H, J = 7.7, 1.4 Hz, Ar-H), 7.23 t.d
(1H, J = 7.4, 1.3 Hz, Ar-H), 7.30 d (1H, J = 8.5 Hz,
Ar-H), 7.65 d.d (1H, J = 7.8, 1.3 Hz, Ar-H), 8.54 s
(1H, H–C=N), 13.27 s (1H, O–H). 13C NMR spectrum,
δC, ppm: 55.55, 101.13, 107.42, 113.19, 117.52, 126.97,
127.19, 127.47, 131.39, 133.88, 146.48, 161.79, 163.61,
164.33. Found, %: C 65.25; H 4.65; N 5.38; S 12.37.
C28H24N2O4S2. Calculated %: C 65.09; H 4.68; N 5.42; S
12.41. M 517 [M + H]+.
1
spectrum, δ, ppm: 6.87 t (1H, J = 7.8 Hz, Ar-H), 6,99
d (1H, J = 7.8 Hz, Ar-H), 7.19 d (1H, J = 7.8 Hz,
Ar-H), 7.29 t (1H, J = 7.6 Hz, Ar-H), 7.38 t (1H, J =
7.5 Hz, Ar-H), 7.54 d (1H, J = 7.8 Hz, Ar-H), 7.48 d
(1H, J = 7.8 Hz, Ar-H), 9.01 s (1H, H–C=N), 9.28 s
(1H, O–H), 12.81 s (1H, O–H). 13C NMR spectrum,
δC, ppm: 101.57, 108.47, 112.25, 114.23, 120.98,
126.64, 127.55, 127.82, 132.27, 145.37, 148.67, 156.85,
166.81. Found, %: C 63.99; H 4.10; N 5.69; S 13.04.
C26H20N2O4S2. Calculated %: C 63.92; H 4.13; N 5.73;
S 13.13. M 489 [M + H]+.
2,2'-{(1Z,1'Z)-[(Disulfanediylbis(2,1-phenylene)]-
bis(azanylylidene)bis(methanylylidene)}bis(4-meth-
oxyphenol) (5c). Bright orange solid, yield 96%, mp
170°C. IR spectrum, ν, cm–1: 2832 (OCH3), 1614
(C=N), 1485 (C=C), 1271 (C–O), 748 (C–S), 577
(S–S). 1H NMR spectrum, δ, ppm: 3.82 s (3H, OCH3),
6.91 d (1H, J = 2.7 Hz, Ar-H), 7.02 d.t (2H, J = 14.0,
5.8 Hz, Ar-H), 7.16 t.d (1H, J = 7.3, 1.4 Hz, Ar-H),
7.20 d.d (1H, J = 7.6, 1.6 Hz, Ar-H), 7.24 d.d (1H, J =
7.5, 1.6 Hz, Ar-H), 7.66 d.d (1H, J = 7.7, 1.5 Hz,
Ar-H), 8.59 s (1H, H–C=N), 12.43 s (1H, O–H). 13C
NMR spectrum, δC, ppm: 55.98, 115.45, 117.63,
118.32, 118.76, 121.15, 127.22, 127.64, 127.77, 131.67,
146.34, 152.36, 155.50, 162.51. Found, %: C 65.17; H
4.64; N 5.38; S 12.38. C28H24N2O4S2. Calculated %: C
65.09; H 4.68; N 5.42; S 12.41. M 517 [M + H]+.
2,2'-{(1Z,1'Z)-[(Disulfanediylbis(2,1-phenylene)]-
bis(azanylylidene)bis(methanylylidene)}bis(benzene-
1,4-diol) (4c). Shiny brown solid, yield 92%, mp 225°C.
IR spectrum, ν, cm–1: 3372 (O–H), 1617 (C=N), 1439
1
(C=C), 1252 (C–O), 758 (C–S), 575 (S–S). H NMR
spectrum, δ, ppm: 6.88 d (1H, J = 8.8 Hz, Ar-H), 6.96
d.d (1H, J = 8.8, 2.9 Hz, Ar-H), 7.17 d (1H, J =
2.9 Hz, Ar-H), 7.28–7.33 m (1H, Ar-H), 7.37 t.d (1H,
J = 7.6, 1.3 Hz, Ar-H), 7.52 d.d (1H, J = 7.8, 0.9 Hz,
Ar-H), 7.58 d.d (1H, J = 7.8, 1.2 Hz, Ar-H), 8.96 s
(1H, H–C=N), 9.23 s (1H, O–H), 11.83 s (1H, O–H).
13C NMR spectrum, δC, ppm: 116.79, 117.37, 118.34,
119.36, 121.84, 125.70, 127.75, 127.92, 130.39,
146.17, 149.78, 153.06, 163.02. Found, %: C 63.80; H
4.19; N 5.79; S 13.02. C26H20N2O4S2. Calculated %: C
63.92; H 4.13; N 5.73; S 13.13. M 489 [M + H]+.
Antimicrobial susceptibility patterns of Acineto-
bacter baumannii. Multiple-resistant A. baumannii
isolates were obtained from various clinical samples
(Medical Microbiology Laboratory of Duzce
University Medical Faculty). Identification of
A. baumannii isolates was performed by conventional
microbiological methods (Gram staining, oxidase,
three sugar iron broth and motion test) and an
automatized-bacterial identification system (Vitek 2,
bioMerieux, France).
6,6'-{(1Z,1'Z)-[(Disulfanediylbis(2,1-phenylene)]-
bis(azanylylidene)bis(methanylylidene)}bis(2-meth-
oxyphenol) (5a). Bright orange solid, yield 96%, mp
174°C. IR spectrum, ν, cm–1: 2839 (OCH3), 1610
(C=N), 1455 (C=C), 1247 (C–O), 729 (C–S), 559
(S–S). 1H NMR spectrum, δ, ppm: 3.96 s (3H, OCH3),
6.98 d (3H, J = 51.5 Hz, Ar-H), 7.19 d (3H, J =
10.2 Hz, Ar-H), 7.68 s (1H, Ar-H), 8.66 s (1H,
H–C=N), 13.26 s (1H, O–H). 13C NMR spectrum, δC,
ppm: 56.39, 116.52, 118.93, 119.38, 119.84, 124.47,
126.68, 128.41, 128.62, 130.88, 146.36, 148.44, 150.78,
164.23. Found, %: C 65.13; H 4.65; N 5.49; S 12.38.
C28H24N2O4S2. Calculated %: C 65.09; H 4.68; N 5.42;
S 12.41. M 517 [M + H]+.
Meropenem and other antibiotic susceptibilities of
A. baumannii isolates were determined by the Vitek 2
system and evaluated according to CLSI [18].
Detection of resistance to typical antibiotics belonging
to at least three antibiotic classes was defined as
multiple antibiotic resistance. Antibacterial activities
of all the compounds were determined by the broth
microdilution method [18]. The compounds were
dissolved in DMSO to a final concentration of 60 μg/mL.
The isolates were adjusted to McFarland’s 0.5 standard
and 100 µL of the Mueller Hinton broth was placed in
each 96-well plate. Afterwards, serial dilutions of the
solutions were carried out. MIC50 and MIC90 values of
6,6'-{(1Z,1'Z)-[(Disulfanediylbis(2,1-phenylene)]-
bis(azanylylidene)bis(methanylylidene)}bis(3-meth-
oxyphenol) (5b). Bright orange solid, yield 97%, mp
198°C. IR spectrum, ν, cm–1: 2839 (OCH3), 1632
(C=N), 1461 (C=C), 1243 (C–O), 757 (C–S), 553
(S–S). 1H NMR spectrum, δ, ppm: 3.86 s (3H, OCH3),
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 2 2018