Med Chem Res
4H, CHphenyl), 7.51–8.25 (m, 4H, CHpyridine), 8.66 (1 s, 1H,
NH exchangeable with D2O), 10.53 (s, 1H, NH
exchangeable with D2O), 12.01 (s, 1H, NH exchangeable
with D2O). 13C NMR (DMSO-d6, 75 MHz) d: 14.79,
124.50, 125.47, 125.89, 129.26, 132.24, 137.81, 139.69,
145.62, 149.68, 150.00, 169.69. FT-IR m: 3236, 3111,
1654, 1324 cm-1. MS (CI) m/z: 318 (M?). Anal.: Calcd.
for C14H14N4OS2 (318.41): C (52.80), H (4.43), N (17.59).
Found: C (52.71), H (4.38), N (17.51).
165.02, 182.69. FT-IR m: 3265, 3113, 1677, 1368 cm-1
.
MS (CI) m/z: 291 (M?). Anal.: Calcd. for C13H11N4OSF
(290.31): C (53.78), H (3.82), N (19.29). Found: C (53.65),
H (3.74), N (19.42) (Byung et al., 2004).
4-(2,4-Dichlorophenyl)-1-(pyridin-4-yl)carbonylthiosemi-
1
carbazide (10) Yield 84 %, m.p. 164–166 °C. H NMR
(DMSO-d6, 300 MHz) d: 7.37–7.45 (m, 3H, CHphenyl),
7.68–8.78 (m, 4H, CHpyridine), 9.76 (s, 1H, NH exchange-
able with D2O), 10.05 (s, 1H, NH exchangeable with D2O),
10.95 (s, 1H, NH exchangeable with D2O). 13C NMR
(DMSO-d6, 75 MHz) d: 122.24, 127.81, 129.30, 132.12,
132.92, 133.27, 136.55, 150.65, 165.09, 182.53. FT-IR m:
3309, 3117, 1677, 1380 cm-1. MS (CI) m/z (%): 341 (M?).
Anal.: Calcd. for C13H10N4OSCl2 (341.21): C (45.75), H
(2.95), N (16.41). Found: C (45.69), H (2.90), N (17.01)
(Goldfarb, 2009).
4-(4-Methylthiophenyl)-1-(pyridin-3-yl)carbonylthiosemi-
1
carbazide (6) Yield 89 %, m.p. 176–177 °C. H NMR
(DMSO-d6, 300 MHz) d: 2.47 (s, 3H, CH3), 7.23–7.57 (m,
4H, CHphenyl), 8.27–8.76 (m, 4H, CHpyridine), 9.11 (s, 1H,
NH exchangeable with D2O), 9.81 (s, 1H, NH exchange-
able with D2O), 10.76 (s, 1H, NH exchangeable with D2O).
13C NMR (DMSO-d6, 75 MHz) d: 15.58, 123.90, 126.24,
127.14, 128.72, 134.96, 136.05, 136.83, 149.40, 152.84,
165.14, 181.53. FT-IR m: 3284, 1632, 1341 cm-1. MS (CI)
m/z (%): 319 (M?). Anal.: Calcd. for C14H14N4OS2
(318.41): C (52.80), H (4.43), N (17.59). Found: C (52.72),
H (4.49), N (17.64).
X-ray analysis
The X-ray diffraction intensities were collected at 100 K
on an Oxford Diffraction Xcalibur CCD diffractometer
with graphite-monochromatized MoKa radiation (k =
4-(2,4-Dichlorophenyl)-1-(pyridin-3-yl)carbonylthiosemi-
carbazide (7) Yield 92 %, m.p. 196–197 °C. 1H (DMSO-
d6, 300 MHz) d: 7.37–7.68 (m, 3H, CHphenyl), 8.27–9.11
(m, 4H, CHpyridine), 9.75 (s, 1H, NH exchangeable with
D2O), 10.02 (s, 1H, NH exchangeable with D2O), 10.86 (s,
1H, NH exchangeable with D2O). 13C NMR (DMSO-d6,
75 MHz) d: 123.96, 129.36, 135.14, 148.55, 152.23,
164.80. FT-IR m: 3331, 3150, 1700, 1359 cm-1. MS (CI)
m/z: 342 (M?). Anal.: Calcd. for C13H10N4OSCl2 (341.21):
C (45.75), H (2.95), N (16.41). Found: C (45.98), H (2.91),
N (16.52) (CAS: 475180-05-3).
˚
0.71073 A) using the x scan technique, with an angular
scan width of 1.0°. The programs CrysAlis CCD and
CrysAlis Red (Oxford Diffraction, Xcalibur CCD System,
CRYSALIS Software System, Version 1.171, Oxford
Diffraction Ltd. 2009) were used for data collection, cell
refinement and data reduction. Absorption corrections were
applied using the multi-scan method by Blessing (Bless-
ing, 1995). The structures were solved via direct methods
using SHELXS-97 and refined by the full-matrix least-
squares on F2 using the SHELXL-97 (Sheldrick, 2008).
Non-hydrogen atoms were refined with anisotropic dis-
placement parameters. The N-bonded H atoms were found
in the difference Fourier maps and then remained fixed
during the least-squares refinements. All the remaining H
atoms were positioned geometrically and allowed to ride
on their parent atoms, with Uiso(H) = 1.2 Ueq(C). The
molecular plots were drawn with Olex2 (Dolomanov
et al., 2009).
4-(4-Methylthiophenyl)-1-(pyridin-4-yl)carbonylthiosemi-
1
carbazide (8) Yield 86 %, m.p. 197–198 °C. H NMR
(DMSO-d6, 300 MHz) d: 2.47 (s, 3H, CH3), 7.23–7.86 (m,
4H, CHphenyl), 8.77–8.78 (m, 4H, CHpyridine), 9.83 (s, 2H,
NH exchangeable with D2O), 10.86 (s, 1H, NH
exchangeable with D2O). 13C NMR (DMSO-d6, 75 MHz)
d: 15.57, 122.15, 126.26, 127.04, 134.97, 136.79, 140.07,
150.67, 164.93, 181.45. FT-IR m: 3097, 2936, 1667,
1378 cm-1. MS (CI) m/z (%): 319 (M?). Anal.: Calcd. for
C14H14N4OS2 (318.41): C (52.80), H (4.43), N (17.59).
Found: C (52.96), H (4.51), N (52.68).
Antibacterial activity
Panel reference strains of bacteria from the American Type
Culture Collection or Polish Collection of Microorganisms,
including aerobic Gram-positive bacteria: Staphylococcus
aureus ATCC 25923 and Staphylococcus epidermidis
ATCC 12228, and aerobic Gram-negative bacteria:
Escherichia coli ATCC 25922 and Pseudomonas aerugi-
nosa ATCC 9027, as well as microaerobic Gram-positive
bacteria: Lactobacillus spp., Lactobacillus acidophilus
PCM 2105, Streptococcus mutans PCM 2502 and
4-(2-Fluorophenyl)-1-(pyridin-4-yl)carbonylthiosemicar-
bazide (9) Yield 78 %, m.p. 202–204 °C. 1H NMR
(DMSO-d6, 300 MHz) d: 7.18–7.31 (m, 4H, CHphenyl),
7.86–8.78 (m, 4H, CHpyridine), 9.70 (s, 1H, NH exchange-
able with D2O), 9.99 (s, 1H, exchangeable with D2O),
10.94 (s, 1H, NH exchangeable with D2O). 13C NMR
(DMSO-d6, 75 MHz) d: 116.14, 116.27, 122.21, 124.44,
127.51, 128.74, 131.17, 140.00, 150.65, 157.08, 158.70,
123