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10 CCDC804781 (for compound 4a) and CCDC804782 (for compound 4d) contain the supplementary crystallographic data
for this paper. These data can be obtained free of charge from The
Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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Representative
Brazilin-Like Compounds
Lactone analogue 4e: pale red syrup. ¹H
NMR (300 MHz, CDCl3): δ = 7.02 (1 H,
d, J = 7.5
Hz), 6.70-6.86 (4 H, m), 4.15 (1 H, s), 3.84 (3 H, s),
3.81 (3 H, s), 3.77 (3 H, s), 3.34 (1 H, d, J = 15.3
Hz), 3.04-3.13 (2 H, m), 2.84 (1 H, d, J = 15.6
Hz) ppm. ¹³C NMR (75 MHz, CDCl3): δ = 148.41, 148.12,
146.88, 137.37, 133.69, 130.87, 122.96, 121.67, 117.82, 108.72,
77.83, 56.10, 55.48, 52.51, 48.07, 42.13 ppm. MS (EI): m/z (%) = 328
(25) [M+ + 1], 327
(100) [M+], 309 (23), 308
(86), 294 (32), 278 (9), 250 (4), 239 (4), 220 (4), 208 (4), 191
(4), 176 (58), 151 (65), 133 (13), 107 (12). HRMS: m/z calcd
for C19H21NO4 [M]+:
327.1471; found: 327.1479.
13 The cytotoxicity assay was carried
out on four cell lines (K562, A549, HT-29, and HL60). Cells were
cultured at 37 ˚C under a humidified atmosphere of 5% CO2 in
RPMI 1640 medium supplemented with 10% fetal serum and
dispersed in replicate 96-well plates. Compounds were then added. After
48 h exposure to the compounds, cells viability were determined
by the [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-
tetrazolium
bromide] (MTT) cytotoxicity assay by measur-ing the absorbance
at λ = 570 nm with a microplate spectrophotometer.
Each test was performed in triplicate. Cisplatin (DDP) was used
as the reference drug.
