Om temperature for 16 h and quenched with H2O (30 mL) and

Om temperature for 16 h and quenched with H2O (30 mL) and extracted with CH2Cl2 (20 mL X 3). Immediately after becoming dried over Na2SO4, the CH2Cl2 was evaporated and also the residue was purified by column chromatography (hexane: EtOAc = two: 1) to afford the item 14a or 14b. five.1.five 1-(1,1-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, 2 H), 7.41 (d, J = 8.7 Hz, 2 H), two.23 (s, 1 H); 13C NMR (75 MHz, CDCl3) 148.5, 141.1, 128.6, 123.8, 123.four, 89.six, 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, 2 H), 7.37 (d, J = eight.7 Hz, two H), 2.63 (q, J = 7.5 Hz, two H), 0.98 (t, J = 7.four Hz, 3 H); 13C NMR (75 MHz, CDCl3) 147.five, 147.0, 146.9, 129.0, 123.8, 89.3, 32.6, 11.3; CIMS m/z 336 (MH+); HRCIMS m/z calcd for C10H10N1O279Br81Br (MH+) 335.DKK-1 Protein Gene ID 9052, discovered 335.9048.Author Manuscript Author Manuscript Author Manuscript Author ManuscriptBioorg Med Chem. Author manuscript; accessible in PMC 2017 November 01.Zhao et al.Page5.1.7 General Procedure for the Synthesis of Triphenylalkenes (12a )–A remedy of 1,1-dibromo-1-alkenes 14a or 14b (1.0 mmol), 4-hydroxyphenylboronic acid or 4-aminophenylboronic acid (4.0 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. Soon after cooling to room temperature, EtOAc (15 mL) and H2O (10 mL) had been poured in to the reaction mixture. The aqueous layer was extracted with EtOAc (20 mL X three). The combined organic layers had been washed with water and dried, concentrated in vacuo and purified by flash column chromatography (hexane: EtOAc = 2:1) to afford the merchandise 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, 2 H), 7.ten (d, J = 8.1 Hz, 2 H), 6.82 (d, J = 8.7 Hz, two H), six.72 (d, J = 9.0 Hz, two H), six.52 (d, J = eight.four Hz, 2 H), 4.78 (s, 1 H), 4.62 (s, 1 H), 2.17 (s, three H); 13C NMR (75 MHz, CDCl3) 154.7, 154.3, 152.1, 145.5, 141.three, 135.two, 134.9, 132.three, 132.1, 131.three, 130.2, 123.two, 115.0, 114.7, 22.9; ESIMS m/z 370 (MNa+); HRESIMS m/z calcd for C21H17NO4Na (MNa+) 370.1055, identified 370.1066; HPLC purity, 100 (90 MeOH, 10 H2O). 5.1.9 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 = eight.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 = eight.1 Hz, 2 H), six.66 (d, J = 8.4 Hz, 2 H), six.62 (s, 2 H), 6.44 (d, J = 9.0 Hz, two H), two.54 (q, J = 7.8 Hz, two H), 0.IL-17A Protein Molecular Weight 90 (t, J = 7.PMID:23833812 8 Hz, 3 H); 13C NMR (75 MHz, methanol-d4) 157.7, 157.1, 152.3, 147.1, 142.8, 139.six, 135.7, 135.3, 133.three, 132.0, 131.six, 128.5, 124.0, 116.8, 116.5, 115.9, 115.five, 29.five, 14.0; damaging ion ESIMS m/z 360 (M sirtuininhibitorH+)-; negative ion HRESIMS m/z calcd for C22H18NO4 (M sirtuininhibitorH+)- 360.1236, identified 360.1237; HPLC purity, 95.18 (90 MeOH, 10 H2O). 5.1.ten 4-(1-(4-Aminophenyl)-2-(4-nitrophenyl)prop-1-enyl)benzenamine (12c)– Brick red strong, 55 yield: mp 202sirtuininhibitor04 . 1H NMR (300 MHz, methanol-d4) 7.97 (d, J = 6.six Hz, 2 H), 7.32 (d, J = 7.2 Hz, two H), 6.96 (d, J = six.9 Hz, two H), six.71 (d, J = six.9 Hz, 2 H), 6.60 (d, J = six.six Hz, two H), 6.41 (d, J = six.9 Hz, two H), 2.16 (s, three H); 13C NMR (75 MHz, methanol-d4) 154.three,.