An effective two-step synthesis, fluorescent properties, antioxidant activity and cytotoxicity evaluation of benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones

Design, synthesis and evaluation of novel 2,2-dimethyl-2,3-dihydroquinolin-4(1H)-one based chalcones as cytotoxic agents

“…Synthetic approaches towards the 4-quinolinone skeleton include the approach of Politanskaya [7] , who used a p -toluene sulfonic acid-catalyzed cyclocondensation reaction of o -alkynylanilines, in turn prepared by the PdCl 2 (PPh 3 ) 2 –catalysed Sonogashira reaction of iodoanilines with 2-methylbut-3-yn-2-ol. Similarly, Pisansechi et al [15] used o -halo or o -trifloxy- N -acetylanilines in the coupling step and hydrochloric acid to induce cyclisation.…”

“…These compounds all possessed an acetic acid ester side chain at C6. More recent publications focus on the cytotoxic potential of quinolinones, notably simple halo-substituted examples such as ( 6 ), which exhibited cytotoxicity, most notably against the RPMI human myeloma cell line with IC 50 s of 13.0–17.5 μM [7] .…”

Fluorinated 3,4-Dihydro-2H-1,4-Benzothiazin- 1,1-Dioxide Derivatives with Antiarrhythmic and Hypertensive Effects

“…The structures of all new products were confirmed by 1 H, 19 F, 13 C NMR; Infrared (IR) spectroscopy; and high-resolution mass spectrometry (HRMS). The molecular and crystal structures of 2 and 3a-c were solved by X-ray crystallography (Figure 2).…”

“…All solvents and SOCl 2 were purified using standard The structures of all new polyfluorinated compounds 2-5 prepared here were corroborated by their 19 F, 1 H and 13 C NMR, high-resolution mass spectrometry, and IR-spectroscopy data (see SI). Signals in the NMR spectra of 2-5 were assigned based on spin coupling constants, which are typical for polyfluorinated benzenes [15][16][17][18][19][20].…”

“…mixture was diluted with H 2 O (50mL) and extracted with CH 2 Cl 2 (2×50mL). The combined organic layers were washed with H 2 O 7 ), 143.0(s,C 13 ), 130.9(dd, 2 J(C 4a ,F 5 )=11.9Hz, C 4a ), 120.7(dd, 2 J(C 8a ,F 8 )=13.0Hz, C 8a ), 110.7(s,C 12 ), 109.6(ddm, 2 J(C 6 ,F 7 )=27.1Hz, 2 J(C 6 ,F 5 )=21.8Hz, C 6 ), 109.5(s, C 11 ), 50.4(d, J(C 9 ,F 5 )=11.4Hz, C 9 ), 49.3(s,C 2 ), 47.3(s,C 3 ) 19. F NMR (282MHz, CDCl 3 ): δ=-120.8(t, J(F 5 ,F 8 )≈J(F 5 ,H 6 )=12.8Hz, 1F, F 5 ), -141.3 (m, J(F 8 ,F 7 )=22.6Hz,J(F 8 ,F 5 )=13.5Hz, J(F 8 ,H 6 )=7.3Hz,1F,F 5 ), -142.7(ddm, J(F 7 ,F 8 )=22.6Hz, J(F 7 ,H 6 )=9.5Hz, 1F, F 7 ).…”