Careful deprotection of the acetyl groups under mildly alkaline condition (NH3?H2O in MeOH) at room temperature afforded the desired three novel 5-deoxyflavonoids-3-O-��-D-glycosides 20~22. The glycosylation selectively affords ��-products by taking the advantage of 2-OAc neighboring Alisertib FDA participation effects to secure the 1, 2-trans glycosylation of each sugar residue. In the 1H NMR spectra of compounds 20~22, the chemical shift of the C1-H in the glycosyl ring appeared downfield (�� 5.5~5.8) with a coupling constant J1,2 = 7.3 ~ 8.0Hz, which confirmed their ��-anomeric configuration [13]. The 22 designed target chalcones 1~8 and 5-deoxyflavonoids 9~22 were exposed to four human cancer cell lines MDA-MB-23 (human breast cancer cell), U251 (human glia cancer cell), BGC-823 (human stomach cancer cell), and B16 (mouse melanoma cell), respectively, for 48h using the sulforhodamine B (SRB) protein staining method with the Hydroxycamptothecin (HCPT), Vincristine, and Taxol as positive control.

It appeared that these closely related molecules displayed a wide range of inhibitory activities against MDA-MB-23, U251, BGC-823, and B16 cancer cells lines at the maximum concentration of 10��g/mL as shown in Table 1. Compounds 2, 4, 5, 6, 10, 15, and 19 showed moderate cytotoxic activity against four cancer cell lines with IC50 values ranging from 2.37 to 9.71��g/mL. Table 1IC50 value (��g/mL) of chalcones and deoxyflavonoids on the cancer cell lines.3. ExperimentalMelting points were measured on a XRC-1 apparatus and were uncorrected. IR spectra were recorded on a Bruker Tensor-27 spectrometer.

1HNMR spectra were recorded on a Bruker AM-500 or Bruker AM-400 instrument, using tetramethylsilane as an internal standard, chemical shifts (��) in ppm, and coupling constants (J) in Hz. Mass spectra were determined with ZAB-HS spectrometer by the EI or FAB method. Elemental analyses were carried out on a PerkinElmer 240B microanalyser. All solvents were dried by standard procedures. ��-Acetylglucose bromide, ��-acetylgalactose bromide, and ��-acetyllactose bromide were prepared as described in detail [14, 15].3.1. General Procedure for the Synthesis of Chalcones 1~8To a stirred solution of KOH (9.3g, 165mmol) in EtOH (40mL) cooled in an ice bath was added dropwise a solution of the corresponding acetophenone (12.9mmol) and aldehyde (12.9mmol) in EtOH (40mL).

The mixture was kept at 0��C for 0.5h and then room temperature for 22h. The mixture was poured into ice water (20mL), adjusted to pH 3~4 with 1mol?L?1 HCl, filtered, and then recrystallized from EtOH to obtain the desired products 1~8, respectively.2��,4��-Hydroxy-4-methoxy chalcone (1): light-yellow needles, yield 91%, and m.p. 178~180��C (lit. [16]: 168~170��C). 1H NMR Brefeldin_A (400MHz, DMSO-d6): �� 3.83 (3H, s, OCH3), 6.