208
N. Chandak et al. / European Journal of Medicinal Chemistry 59 (2013) 203e208
stretch), 1335
&
1165 (s, SO2 stretch); 1H NMR (DMSO-d6,
with antibiotics (200-unit having concentration of penicillin
100 IU/mL and streptomycin 100 IU/mL) in CO2 incubator (5% CO2,
95% humidity, 38 ꢃC). The cells were plated at a density of 105 cells/
300 MHz): d 9.11 (s, 1H, imidazo C4eH), 8.57 (s, 1H, Ar), 8.31 (d, 2H,
J ¼ 8.1 Hz, Ar), 8.16 (d, 1H, J ¼ 8.4 Hz, Ar), 8.11 (d, 2H, J ¼ 8.1 Hz, Ar),
8.02 (d, 1H, J ¼ 8.4 Hz, Ar), 7.53 (s, ex, 2H, SO2NH2); 13C NMR
mL and pre-incubated with 10
DMSO for 30 min before induction of apoptosis. Then the apoptosis
was induced with 5 M malathion in DMSO. The cell apoptosis was
mM of each tested compound in
(DMSO-d6, 75.5 MHz):
d 149.5, 146.6, 145.0, 141.5, 140.4, 133.9,
130.5, 125.8, 125.0, 124.7, 123.5, 114.3, 112.6; DART-MS: m/z 375.06
m
(M þ H)þ, C15H10N4O4S2Hþ calcd. 375.01.
assayed by Acridine Orange staining after 6 h of culture duration
under the fluorescence microscope (Olympus, Japan) using 500e
525 nm filters [5,24]. Normal cells were identified by their intact
cell membranes and round nucleus with scanty chromatin. Cells
with bright green condensed nuclei (intact or fragmented) were
interpreted as apoptotic.
4.1.7. 2-(2-Oxo-2H-chromen-3-yl)imidazo[2,1-b][1,3]benzothia-
zole-7-sulfonamide (5a)
Yield: 85%; m.p. > 330 ꢃC; IR (KBr) cmꢀ1: 3271 & 3140 (m, NeH
stretch), 1720 (s, lactone C]O stretch), 1605 (s, C]N stretch), 1497
(s, C]C stretch), 1311 & 1157 (s, SO2 stretch); 1H NMR (DMSO-d6,
300 MHz): d 8.87 (s, 1H, imidazo C4eH), 8.62 (s, 1H, Ar), 8.51 (s, 1H,
Acknowledgements
coumarin C4eH), 8.35 (d, 1H, J ¼ 8.4 Hz, Ar), 7.94 (d, 1H, J ¼ 8.4 Hz,
Ar), 7.80 (d, 1H, J ¼ 7.5 Hz, coumarin), 7.49e7.56 (m, 3H, SO2NH2,
coumarin), 7.37 (d, 1H, J ¼ 8.1 Hz, coumarin), 7.30 (t, 1H, J ¼ 7.2 Hz,
Defence Research and Development Organization (DRDO), New
Delhi is thankfully acknowledged for financial support in the form
of a research project. Navneet Chandak is grateful to the Council of
Scientific and Industrial Research (CSIR), New Delhi for the award of
senior research fellowship. The authors are thankful to Sophisti-
cated Analytical Instrument Facility, Central Drug Research Insti-
tute, Lucknow for Mass spectra.
coumarin); 13C NMR (DMSO-d6, 75.5 MHz):
d 158.9, 152.7, 141.4,
140.5, 137.3, 134.1, 131.9, 130.3,129.1, 125.2, 124.9, 123.3,120.4,119.7,
116.3,114.6, 114.3; DART-MS: m/z 398.12 (M þ H)þ, C18H11N3O4S2Hþ
calcd. 398.01.
4.1.8. 2-(6-Chloro-2-oxo-2H-chromen-3-yl)imidazo[2,1-b][1,3]
benzothiazole-7-sulfonamide (5b)
Yield: 80%; m.p. > 330 ꢃC; IR (KBr) cmꢀ1: 3348 & 3163 (m, NeH
stretch), 1720 (s, lactone C]O stretch), 1597 (s, C]N stretch), 1497
(s, C]C stretch), 1327 & 1157 (s, SO2 stretch); 1H NMR (DMSO-d6,
Appendix A. Supplementary data
Supplementary data related to this article can be found at http://
300 MHz): d 8.93 (s, 1H, imidazo C4eH), 8.64 (s, 1H, Ar), 8.53 (s, 1H,
coumarin C4eH), 8.39 (d, 1H, J ¼ 8.4 Hz, Ar), 7.94e7.98 (m, 2H, Ar,
coumarin C5eH), 7.57 (d, 1H, J ¼ 8.7 Hz, coumarin), 7.51 (s, ex, 2H,
SO2NH2), 7.44 (d, 1H, J ¼ 8.4 Hz, coumarin); 13C NMR (DMSO-d6,
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