The Kelch-like ECH-associated protein 1 (Keap1)/nuclear factor erythroid 2-related factor 2 (Nrf2)/antioxidant response elements pathway enables cells to survive oxidative stress conditions through regulating the expression of cytoprotective enzymes such as for example NAD(P)H:quinone oxidoreductase 1 (NQO1). in the binding pocket (Arg483, Tyr525, and Phe478) set alongside the indigenous ligand or any additional compound with this series. (%): 319 (M+) (3.23), 204 (100). Calculated for C21H25N3 (319): C, 78.96; H, 7.89; N, 13.15. Found out: C, 78.59; H, 8.13; N, 12.81. (%): 333 (M+) (12.7), 255 (100). Calculated for C22H27N3 (333.47): C, 79.24; H, 8.16; N, 12.60. Found out: C, 79.50; H, 7.84; N, 12.25. 2-Phenyl-(%): 318 (M+) (22.5), 247 (100). Calculated for C20H22N4 (318): C, 75.44; H, 6.96; N, 17.60. Found out: C, 75.09; H, 6.63; U-69593 IC50 N, 17.92. (%): 332 (M+) (21.6), 316 (100). Calculated for C21H24N4 (332): C, 75.87; H, 7.28; N, 16.85. Found out: C, 76.11; H, 7.57; N, 17.20. (%): 328 (M+) (3.26), 248 (100). Calculated for C21H20N4 (328): C, 76.80; H, 6.14; N, 17.06. Found out: C, 76.55; H, 6.47; N, 16.81. 1-(3-(2-Phenylquinazolin-4-ylamino)propyl)pyrrolidin-2-one (7) Produce, 88%; mp 360C. IR (cm?1): 3,370 (NH), 3,100 (arom), 2,932, 2,847, (aliph), 1,654 (CO), 1,572 (CN). 1H NMR: 1.5C3.2 [m, 6H, 3CH2 Cyclo], 1.9 [m, 2H, CH2-(%): 346 (M+) (15.38), 317 (100). Calculated for C21H22N4O (346): C, 72.81; H, 6.40; N, 16.17. Found out: C, 72.54; H, 6.08; N, 16.46. (%): 315 (M+) (9.54), 286 (100). Calculated for C19H17N5 (315): C, 72.36; H, 5.43; N, 22.21. Found out: C, 72.69; H, 5.16; N, 22.51. 1,5-Dimethyl-2-phenyl-4-(2-phenylquinazolin-4-ylamino)-1,2-dihydropyrazol-3-one (9) Produce, 84%; mp 149CC150C. IR (cm?1): 3,413 (NH), 3,060 (arom), 2,923, 2,839, (aliph), 1,654 (CO), 1,618 (CN). 1H NMR: 2.3 [s, 3H, CH3], 3.1 [s, 3H, N-CH3], 7.3C8.5 [m, 14H, Ar-H], 9.4 [s, 1H, NH]. 13C NMR: Rabbit Polyclonal to MLK1/2 (phospho-Thr312/266) 11.6, 31.2, 114.2 (2), 123.6, 124.0 (2), 126.2, 126.7 (2), 128.2, 128.4, 128.7 (2), 129.6 (2), 130.6 (2), 133.5, 135.9, 138.8, 150.8, 159.5, 160.1, 162.7. MS (%): 407 (M+) (5.98), 331 (100). Calculated for C25H21N5O (407): C, 73.69; H, 5.19; N, 17.19. Found out: C, 73.44; H, 5.50; N, 17.56. (%): 329 (M+) (17.23), 288 (100). Calculated for C20H19N5 (329): C, 72.93; H, 5.81; N, 21.26. Found out: C, 72.71; H, 5.49; N, 20.93. (%): 360 (M+) (33.85), 344 (100). Calculated for C23H28N4 (360): C, 76.63; H, 7.83; N, 15.54. Found out: C, 76.91; H, 7.49; N, 15.22. 2-Phenyl-(%): 332 (M+) (45.11), 219 (100). Calculated for C21H24N4 (332.20): C, 75.87; H, 7.28; N, 16.85. Found out: C, 76.11; H, 7.55; N, 17.10. (%): 334 (M+) (22.17), 256 (100). Calculated for C20H22N4O (334): C, 71.83; H, 6.63; N, 16.75. Found out: C, 71.50; U-69593 IC50 H, 6.30; N, 16.45. (%): 348 (M+) (10.62), 221 (100). Calculated for C21H24N4O (348): C, 72.39; H, 6.94; U-69593 IC50 N, 16.08. Found out: C, 72.08; H, 6.60; N, 16.35. (%): 394 (M+) (5.88), 314 (100). Calculated for C26H26N4 (394.22): C, 79.16; H, 6.64; N, 14.20. Found out: C, 79.48; H, 6.36; N, 13.83. 6-(2-Penylquinazolin-4-ylamino)hexanoic acidity (16a) Produce, 76%; mp 163CC165C. IR (cm?1): 3,438 (OH), 3,311 (NH), 3,078 (arom), 2,939, 2,854 (aliph), 1,687 (CO), 1,613 (CN). 1H NMR: 1.4C1.8 [m, 6H, 3CH2], 2.2 [t, 2H, CH2CO], 3.8 [t, 2H, NH-CH2], 7.3C8.8 [m, 9H, Ar-H], 10.5 [s, 1H, NH], 14.9 [s, 1H, OH]. 13C NMR: 24.6, 26.3, 28.3, 34.0, 41.9, 112.6, 126.8, 128.2 (2), 129.4 (2), 129.6 (2), 133.7 (2), 135.8, 157.4 (2), 160.2, 174.8. MS (%): 335 (M+) (39.45), 290 (100). Calculated for C20H21N3O2 (335): C, 71.62; H, 6.31; N, 12.53. Found out: C, 71.29; H, 6.60; N, 12.19. Biological evaluation Hepa1c1c7 murine hepatoma cells had been grown inside a humidified atmosphere at 37C, 5% CO2. The cell tradition moderate was -minimal essential moderate (-MEM) and was supplemented with 10% (v/v) warmth- and charcoal-inactivated fetal bovine serum. For evaluation from the potential NQO1 inducer activity, cells (104 per well) had been produced in 96-well plates every day and night,.