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Cl3); IR cm-1 (KBr): 3447, 2930, 1713, 1483, 1583, 1233, 1036; 1H NMR (500 MHz, CDCl3) : 7.43 (s, 1H, H-
Cl3); IR cm-1 (KBr): 3447, 2930, 1713, 1483, 1583, 1233, 1036; 1H NMR (500 MHz, CDCl3) : 7.43 (s, 1H, H-5), six.52 (s, 1H, H-8), 6.07 (s, 1H, H-6), 5.99 (d, J = eight.0 Hz, 2H, OCH2O), 5.35 (d, J = five.5 Hz, 1H, H-1), four.79 (t, J = 9.0 Hz, 1H, H-11), 4.01sirtuininhibitor.09 (m, 1H, H-11), three.87 (s, 3H, OCH3), three.85 (s, 3H, OCH3), three.79sirtuininhibitor.84 (m, 1H, H-3), three.62 (s, 3H, OCH3), three.28 (dd, J = 13.0, 5.5 Hz, 1H, H-2); HRMS m/z calcd for MIP-1 alpha/CCL3 Protein medchemexpress C22H21O8NCl ([M+H]+) 462.0950, identified 462.0943. Information for 11: Yield = 63 , white strong, m.p. 200sirtuininhibitor01 ; []20D = -150 (c 2.four mg/mL, CHCl3); IR cm-1 (KBr): 3437, 3108, 2938, 1711, 1480, 1230, 1096; 1H NMR (500 MHz, CDCl3) : 7.37 (s, 1H, H-5), 6.33 (s, 1H, H-8), five.98 (d, J = 3.five Hz, 2H, OCH2O), five.72 (d, J = 8.5 Hz, 1H, H-1), 4.74sirtuininhibitor.78 (m, 1H, H-11), four.51sirtuininhibitor.56 (m, 1H, H-11), three.94 (s, 3H, OCH3), three.89 (s, 3H, OCH3), three.76sirtuininhibitor.80 (m, 4H, H-3 and OCH3), three.38 (dd, J = 13.0, 8.five Hz, 1H, H-2); HRMS m/z calcd for C22H20O8NCl2 ([M+H]+) 496.0560, identified 496.0553. Information for 12: Yield = 60 , white solid, m.p. 194sirtuininhibitor95 ; []20D = -109 (c 2.7 mg/mL, CHCl3); IR cm-1 (KBr): 3446, 3058, 2936.1709, 1482, 1234, 1105; 1H NMR (500 MHz, CDCl3) : 7.37 (s, 1H, H-5), six.45 (s, 1H, H-8), six.15 (s, 1H, H-6), five.98 (d, J = 16.5 Hz, 2H, OCH2O), five.24 (d, J = five.0 Hz, 1H, H-1), 4.73 (t, J = 8.five Hz, 1H, H-11), three.98sirtuininhibitor.05 (m, 1H, H-11), three.81 (s, 3H, OCH3), three.80 (s, 3H, OCH3), three.71sirtuininhibitor.76 (m, 1H, H-3), three.59 (s, 3H, OCH3), 3.03 (dd, J = 12.five, six.0 Hz, 1H, H-2); HRMS m/z calcd for C22H21O8NBr ([M+H]+) 506.0445, discovered 506.0440.N-dicyclohexylcarbodiimide (DCC, 0.2 mmol), 4-dimethylaminopyridine (DMAP, 0.04 mmol), and two(2,6)-(di) halogeno-isoxazolopodophyllic acids (ten, 11, or 12, 0.2 mmol) in dry DCM (ten mL) was stirred at space temperature. When the reaction was full as outlined by TLC CA125 Protein manufacturer evaluation, the mixture was diluted by DCM (40 mL), washed by water (20 mL), aq. HCl (0.1 mol/L, 20 mL), saturated aq. NaHCO3 (20 mL) and brine (20 mL), dried more than anhydrous Na2SO4, concentrated in vacuo, and purified by PTLC to provide compounds Ia ,e ; IIa ; and IIIa in 47sirtuininhibitor3 yields. The instance information of Ia ; IIa ; and IIIa are listed as follows, whereas data of Ie ; IId ; and IIId is usually found in the Supporting Info. Data for Ia: Yield = 63 , white strong, m.p. 155sirtuininhibitor56 ; []20D = -81 (c three.0 mg/mL, CHCl3); IR cm-1 (KBr): 3094, 2937, 1736, 1484, 1233, 1109; 1H NMR (500 MHz, CDCl3) : 7.43 (s, 1H, H-5), 6.50 (s, 1H, H-8), 6.08 (s, 1, H, H-6), 5.99 (dd, J = eight.0, 1.5 Hz, 2H, OCH2O), 5.31 (d, J = 5.five Hz, 1H, H-1), 4.78sirtuininhibitor.81 (m, 1H, H-11), 4.06sirtuininhibitor.13 (m, 1H, H-11), three.89 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.76sirtuininhibitor.80 (m, 1H, H-3), three.62 (s, 3H, OCH3), three.61 (s, 3H, CO2CH3), three.27 (dd, J = 13.0, five.five Hz, 1H, H-2); HRMS m/z calcd for C23H23O8NCl ([M+H]+) 476.1107, identified 476.1099. Information for Ib: Yield = 54 , white solid, m.p. 129sirtuininhibitor30 , []20D = -91 (c three.0 mg/mL, CHCl3); IR cm-1 (KBr): 3036, 2931, 1728, 1484, 1232, 1110; 1H NMR (500 MHz, CDCl3) : 7.43 (s, 1H, H-5), six.51 (s, 1H, H-8), six.11 (s, 1H,Basic process for synthesis of two(2,six)-(di)halogeno-isoxazolopodophyllic acids-based esters (Ia ,e ; IIa ; and IIIa ). A mixture in the corresponding alcohols R1OH (0.28 mmol), N,Scientific RepoRts | 6:33062 | DOI: 10.1038/srepwww.nature/scientificreports/Figure three. Preparation of 2(2,six)-(di)halogeno-isoxazolopodophyllic aci.