At room temperature. When the reaction was full checked by TLC
At room temperature. When the reaction was comprehensive checked by TLC evaluation, the mixture was diluted by DCM (60 mL), washed by saturated aq. NaHSO3 (30 mL) and brine (30 mL), dried over anhydrous Na2SO4, concentrated below decreased FAP Protein medchemexpress stress, and purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (two:3, v/v) to afford compounds 7sirtuininhibitor. Data for 7: CAS: 1458601-16-5. Yield = 81 , white solid, m.p. 217sirtuininhibitor18 [lit. 218sirtuininhibitor19 ]27; []20D = -64 (c two.7 mg/mL, CHCl3); IR cm-1 (KBr): 3075, 2933, 1787, 1685, 1487, 1391, 1117, 1020; 1H NMR (500 MHz, CDCl3) : 7.49 (s, 1H, H-5), 6.57 (s, 1H, H-8), 6.19 (s, 1H, H-6), 6.05 (d, J = three.0 Hz, 2H, OCH2O), five.42 (d, J = 5.five Hz, 1H, H-1), 4.58sirtuininhibitor.62 (m, 1H, H-11), 4.33sirtuininhibitor.36 (t, J = 9.five Hz, 1H, H-11), 3.92 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), three.76sirtuininhibitor.80 (m, 1H, H-3), 3.65 (s, 3H, OCH3), 3.40 (dd, J = 16.0, five.five Hz, 1H, H-2); HRMS (ESI): Calcd for C22H19ClO8Na ([M+Na]+) 469.0671, discovered 469.0660. Information for 8: Yield = 85 , white solid, m.p. 224sirtuininhibitor25 ; []20D = -80 (c three.0 mg/mL, CHCl3); IR cm-1 (KBr): 3084, 2937, 1789, 1686, 1479, 1395, 1249, 1062; 1H NMR (500 MHz, CDCl3) : 7.47 (s, 1H, H-5), 6.49 (s, 1H, H-8), 6.05 (s, 2H, OCH2O), five.73 (d, J = 7.5 Hz, 1H, H-1), four.59sirtuininhibitor.62 (m, 1H, H-11), 4.28sirtuininhibitor.35 (m, 1H, H-11), 3.97 (s, 3H, OCH3), three.96 (s, 3H, OCH3), 3.82sirtuininhibitor.86 (m, 4H, H-3 and OCH3), three.52sirtuininhibitor.57 (m, 1H, H-2); HRMS m/z calcd for C22H21O8NCl ([M+H]+) 481.0451, discovered 481.0447. Information for 9: CAS: 37158-57-9. Yield = 83 , white strong, m.p. 222sirtuininhibitor23 [lit. 220sirtuininhibitor21 ]27; []20D = -93 (c 2.9 mg/mL, CHCl3); IR cm-1 (KBr): 3074, 2934, 1789, 1685, 1479, 1391, 1196, 1075; 1H NMR (500 MHz, CDCl3) : 7.50 (s, 1H, H-5), six.57 (s, 1H, H-8), 6.18 (s, 1H, H-6), six.06 (d, J = three.5 Hz, 2H, OCH2O), 5.52 (d, J = four.5 Hz, 1H, H-1), four.60sirtuininhibitor.64 (m, 1H, H-11), 4.34sirtuininhibitor.38 (m, 1H, H-11), three.92 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), three.80sirtuininhibitor.84 (m, 1H, H-3), 3.64 (s, 3H, OCH3), three.40 (dd, J = 16.0, 5.5 Hz, 1H, H-2); HRMS (ESI): Calcd for C22H19BrO8Na ([M+ Na]+) 513.0154, discovered 513.0155.MethodsGeneral procedure for synthesis of two(two,six)-(di)halogenopodophyllones (7sirtuininhibitor).Basic process for synthesis of 2(two,six)-(di)halogeno-isoxazolopodophyllic acids (10sirtuininhibitor12) and oximes of 2(2,6)-(di)halogenopodophyllones (13sirtuininhibitor5). A mixture of two (two ,six )-(di)Scientific RepoRts | six:33062 | DOI: 10.1038/srepwww.nature/scientificreports/Figure two. The synthetic route for the preparation of compounds 10sirtuininhibitor5.halogenopodophyllone (7, 8 or 9, 1 mmol), hydroxylamine hydrochloride (1.5 mmol), and pyridine (four mmol) in absolute ethanol (20 mL) was refluxed. When the reaction was comprehensive checked by TLC analysis, the solvent was removed beneath lowered pressure, and saturated aq. NaHCO3 (15 mL) was added for the residue, which was extracted with ethyl acetate (three sirtuininhibitor30 mL). The combined organic phase was dried more than anhydrous Na2SO4, filtered, concentrated below decreased stress, and purified by silica gel column chromatography eluting with DCM/ methanol (98:2, v/v) to afford compounds 10sirtuininhibitor5. For compounds 13sirtuininhibitor5 were not steady, they were made use of directly for the subsequent step. Data for ten: Yield = 65 , white strong, m.p. MIP-1 alpha/CCL3 Protein Accession 174sirtuininhibitor75 ; []20D = -78 (c two.0 mg/mL, CH.
