Synthesis of a new series of 2-(2-/3-/4-fluorophenyl)-4-O alkyl quinoline compounds and biologocal activities

In this study, first of all, flour substituted chalcones (3-5) were analogs of natural chalcone compounds were synthesized from o-aminoacetophenone and flour substituted benzaldehyde. In the second step, azaflavanone (6-8) were synthesized from chalcone compounds (3-5) by microwave methods. In the third step of this work, azaflavanones (6-8) were treated with alkyl halides (C5-C15-Br) under basic conditions (KOH) in DMF to yield 33 new quinoline compounds (9a-k, 10a-k and 11a-k). Quinolines were synthesized form azaflavanone for the first time in this work, presumably by air oxidation. The structure of synthesized compounds (3-5, 6-8, 9a-k, 10a-k, and 11a-k) were assigned by spectroscopic techniques (1H-NMR, 13C-NMR, FT-IR, UV, LC-MS/MS and elemental analysis). All of the synthesized compounds (3-5, 6-8, 9a-k, 10a-k, and 11a-k) were tested for their antimicrobial, antioxidant and anti-tumor activities. Antimicrobial MIC values (62.5-500 µg/mL) of synthetic compounds were determined. Antioxidant activity tests of synthetic compounds were carried out using the DPPH and FRAP techniques and anti-tumor activity tests were made against uterus cancer cells (HeLa).