Om temperature for 16 h and quenched with H2O (30 mL) and
Om temperature for 16 h and quenched with H2O (30 mL) and DSG3 Protein Purity & Documentation extracted with CH2Cl2 (20 mL X 3). Immediately after being dried over Na2SO4, the CH2Cl2 was evaporated along with the residue was purified by column chromatography (hexane: EtOAc = 2: 1) to afford the solution 14a or 14b. 5.1.five 1-(1,Complement C3/C3a Protein medchemexpress 1-Dibromoprop-1-en-2-yl)-4-nitrobenzene (14a)–White solid, 65 yield, mp 81sirtuininhibitor2 . 1H NMR (300 MHz, CDCl3) eight.23 (d, J = eight.7 Hz, two H), 7.41 (d, J = eight.7 Hz, two H), 2.23 (s, 1 H); 13C NMR (75 MHz, CDCl3) 148.five, 141.1, 128.6, 123.8, 123.4, 89.6, 25.9; CIMS m/z 321 (MH+). five.1.six 1-(1,1-Dibromobut-1-en-2-yl)-4-nitrobenzene (14b)–White solid, 50 yield: mp 57sirtuininhibitor8 . 1H NMR (300 MHz, CDCl3) 8.24 (d, J = 8.7 Hz, two H), 7.37 (d, J = eight.7 Hz, 2 H), 2.63 (q, J = 7.five Hz, 2 H), 0.98 (t, J = 7.4 Hz, 3 H); 13C NMR (75 MHz, CDCl3) 147.5, 147.0, 146.9, 129.0, 123.eight, 89.3, 32.6, 11.3; CIMS m/z 336 (MH+); HRCIMS m/z calcd for C10H10N1O279Br81Br (MH+) 335.9052, found 335.9048.Author Manuscript Author Manuscript Author Manuscript Author ManuscriptBioorg Med Chem. Author manuscript; offered in PMC 2017 November 01.Zhao et al.Page5.1.7 Basic Process for the Synthesis of Triphenylalkenes (12a )–A answer of 1,1-dibromo-1-alkenes 14a or 14b (1.0 mmol), 4-hydroxyphenylboronic acid or 4-aminophenylboronic acid (four.0 mmol), PdCl2(PPh3)two (0.1 mmol), and Na2CO3 (three.0 mmol) in THF-H2O (15 mL) was heated to 70 under Ar2 for 18 h. After cooling to area temperature, EtOAc (15 mL) and H2O (10 mL) have been poured in to the reaction mixture. The aqueous layer was extracted with EtOAc (20 mL X 3). The combined organic layers have been washed with water and dried, concentrated in vacuo and purified by flash column chromatography (hexane: EtOAc = two:1) to afford the goods 12a . five.1.eight 4-(1-(4-Hydroxyphenyl)-2-(4-nitrophenyl)prop-1-enyl)phenol (12a)–Light brown solid, 67 yield: mp 235sirtuininhibitor36 . 1H NMR (300 MHz, CDCl3) 8.02 (d, J = 9.0 Hz, two H), 7.28 (d, J = 7.8 Hz, two H), 7.ten (d, J = 8.1 Hz, 2 H), six.82 (d, J = 8.7 Hz, 2 H), 6.72 (d, J = 9.0 Hz, 2 H), six.52 (d, J = 8.four Hz, 2 H), four.78 (s, 1 H), 4.62 (s, 1 H), two.17 (s, 3 H); 13C NMR (75 MHz, CDCl3) 154.7, 154.3, 152.1, 145.5, 141.3, 135.2, 134.9, 132.three, 132.1, 131.three, 130.2, 123.2, 115.0, 114.7, 22.9; ESIMS m/z 370 (MNa+); HRESIMS m/z calcd for C21H17NO4Na (MNa+) 370.1055, discovered 370.1066; HPLC purity, one hundred (90 MeOH, ten H2O). five.1.9 4-(1-(4-Hydroxyphenyl)-2-(4-nitrophenyl)but-1-enyl)phenol (12b)–Pale yellow solid, 57 yield: mp 111sirtuininhibitor12 . 1H NMR (300 MHz, methanol-d4) 7.99 (d, J = 8.7 Hz, 2 H), 7.29 (d, J = 8.7 Hz, two H), 7.03 (d, J = eight.7 Hz, two H), 6.77 (d, J = 8.1 Hz, 2 H), 6.66 (d, J = 8.four Hz, two H), 6.62 (s, 2 H), six.44 (d, J = 9.0 Hz, two H), 2.54 (q, J = 7.8 Hz, 2 H), 0.90 (t, J = 7.eight Hz, 3 H); 13C NMR (75 MHz, methanol-d4) 157.7, 157.1, 152.three, 147.1, 142.eight, 139.six, 135.7, 135.3, 133.three, 132.0, 131.6, 128.5, 124.0, 116.8, 116.5, 115.9, 115.5, 29.5, 14.0; negative ion ESIMS m/z 360 (M sirtuininhibitorH+)-; adverse ion HRESIMS m/z calcd for C22H18NO4 (M sirtuininhibitorH+)- 360.1236, located 360.1237; HPLC purity, 95.18 (90 MeOH, 10 H2O). five.1.ten 4-(1-(4-Aminophenyl)-2-(4-nitrophenyl)prop-1-enyl)benzenamine (12c)– Brick red solid, 55 yield: mp 202sirtuininhibitor04 . 1H NMR (300 MHz, methanol-d4) 7.97 (d, J = six.6 Hz, two H), 7.32 (d, J = 7.2 Hz, 2 H), 6.96 (d, J = 6.9 Hz, two H), 6.71 (d, J = 6.9 Hz, two H), 6.60 (d, J = six.six Hz, two H), six.41 (d, J = 6.9 Hz, 2 H), two.16 (s, three H); 13C NMR (75 MHz, methanol-d4) 154.three,.