acta 2_2015

Anticancer activity of newly synthesized triazolopyrimidine... 311Table 1. In vitro cytotoxicity activity of the synthesized compounds in three human cancer cell lines as measuredwith SRB assay.IC 50 (µg/mL)CompoundMCF-7 A549 HCT116Doxorubicin 2.90 ± 0.27 4.30 ± 0.40 4.80 ± 0.50DMSO N.A. N.A. N.A.2 4.80 ± 0.55 8.20 ± 0.78 75.40 ± 8.803 2.80 ± 0.33 4.20 ± 0.50 75.00 ± 7.304 N.A. N.A. N.A.6 14.70 ± 1.75 33.20 ± 5.00 N.A.7a N.A. N.A. N.A.9 3.90 ± 0.42 8.00 ± 0.83 80.70 ± 9.3010 3.60 ± 0.39 6.50 ± 0.67 66.80 ± 7.5011 22.70 ± 2.50 28.00 ± 3.29 88.50 ± 9.4012a N.A. N.A. N.A.Data were expressed as the mean ± standard error (SE) of six independent experiments. N.A. is no activity.Compound 3Compound 6Compound 10Compound 11Compound 9Compound 2DoxorubicinFigure 1. Effect of treatment with various concentrations of prepared compounds on breast MCF-7 cell line cytotoxicity (IC 50 ) as measuredwith SRB method(Z)-3-(4-Methoxybenzyl)-5-(hydrazinylsugar)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one(12a-c)General procedureTo a well-stirred solution of the respectivemonosaccharide (0.01 mol) in water (2 mL), andglacial acetic acid (0.2 mL) was added the hydrazinederivative 11 (10 mmol) in ethanol (15 mL). Themixture was heated under reflux for 4-6 h (TLC) andthe resulting solution was concentrated and left tocool. The precipitate formed was filtered off,washed with water, then dried and crystallized fromethanol-DMF (2 : 1, v/v).(Z)-3-(4-Methoxybenzyl)-5-(per-O-acetylhydrazinylsugar)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one(13a-c)General procedureTo a solution of the hydrazinyl sugar derivative12a-c (5 mmol) in pyridine (10 mL) was addedacetic anhydride (6 mmol) and the mixture wasstirred at room temperature for 7 h. The resultingsolution was poured onto crushed ice, and the productthat separated out was filtered off, washed withsodium hydrogen carbonate and water, then dried toafford compounds 13a-c.