1-Aryl-4,6-dihydropyrazolo[4,3-d][1]benzazepin-5(1H)-ones: A new class of antiproliferative agents with selectivity for human leukemia and breast cancer cell lines

A Facile Synthesis of Face “D” Quinolino Annulated Benzazepinone Analogues with Its Quinoline Framework Appended To Oxadiazole, Triazole and Pyrazole Heterocycles

“…), 3090 (C-H str. ), 2900, 1400 (-CH 2 Synthesis of 7-(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-2-fluoro-5H-benzo [2,3] azepino [4,5-b]quinolin-6-(7H)-one (8).…”

“…The product obtained on drying (over anhydrous sodium sulfate) and evaporation of the ether layer was dissolved in ethanol (10 mL), and hydrazine hydrate (1 mL, 0.02 mol) was added. The mixture was refluxed for 10 h. The product that settled on cooling was recrystallized with ethanol to give compound 4 (0.90 g, yield 70%); mp 180-182°C; IR (KBr) cm Synthesis of 2-fluoro-8-(5-mercapto-4H-1,2,4-triazol-3-yl)-7,7a-dihydro-5H-benzo [2,3]azepino- [4,5-b]quinolin-6-(13aH)-one (7). A mixture of carbohydrazide (4) (0.64 g, 0.002 mol) and potassium thiocyanate (0.776 g, 0.008 mol), conc.…”

“…The product was extracted with ethyl acetate (3 × 10 mL). The extract was dried over anhydrous Na 2 SO 4 Synthesis of 2-fluoro-6-oxo-6,7,7a,13a-tetrahydro-5H-benzo [2,3]azepino [4,5-b]quinoline-8-carbohydrazide (4). To a solution of compound 3 (1.28 g, 0.004 mol) in methanol (25 mL), conc.…”

“…HCl. The solid obtained was filtered and recrystallized with methanol to give 2-fluoro-8-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-5H-benzo- [2,3] azepino [4,5- A mixture of carbohydrazide (4) (0.64 g, 0.002 mol) and ethoxymethylenemalono nitrile (0.24 g, 0.002 mol) was stirred for 2 h and then ethanol (20 mL) was added. The mixture was stirred at room temperature for 25 h. The solid product obtained was filtered and recrystallized with methanol-water to give compound 9 (0.41 g, yield: 64%); mp 130-132°C; IR (KBr) cm À1 : 3400 (NH 2 ), 3220 (N-H str.…”

“…The advent of an impressive anti-proliferative [1] and anti-leukemic [2,3] activity in face "d" indolo annulated analogue of benzazepinone, namely the paullone, was hailed as a major step forward in the direction of developing potentially useful agents to combat these diseases, from this class of compounds. This discovery provided an impetus for us to design and develop a focused library of other hetero-ring annulated benzazepinone analogues bearing such bioactive scaffolds as pyrazole, isoxazole, pyrimidine, and quinoline in its molecule.…”