Synthesis, structure-activity relationships and preliminary mechanism of action of novel water-soluble 4-quinolone-3-carboxamides as antiproliferative agents

Design, synthesis, and biological evaluation of novel arylcarboxamide derivatives as anti-tubercular agents

“… 54 – 56 The 7-bromo derivative 9g was the only isomer that could be isolated as a product from the starting material 3-bromoaniline and it was difficult to characterise its chemical structure by 1 H NMR due its poor solubility even in DMSO-d 6 as previously reported. 57 …”

Effect of a newly synthesized quinoline-based compound (PPQ-8) on murine schistosomiasis mansoni

“…Quinoline pharmacophore has a diverse variety of pharmacological activities, which include anti-tubercular (Fan et al ., 2018a), anti-bacterial (Zhang et al ., 2018), anti-protozoan (Fan et al ., 2018b), anti-fungal (Musiol et al ., 2006), anti-oxidant (Wilhelm et al ., 2017), anti-proliferative (Zhang et al ., 2017), anti-tumour (Sharma et al ., 2013), anti-inflammatory (Upadhyay et al ., 2018), anti-hypertensive (Muruganantham et al ., 2004) and anti-HIV effects (Luo et al ., 2010). Moreover, quinolines can be used for treatment of lupus (Bengtsson et al ., 2012) and neurodegenerative diseases (Wang et al ., 2018).…”

Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones

“…13 C NMR (125 Hz, CDCl 3 ) δ 1.5 (q), 39.0 (t), 42.4 (q), 69.1 (d), 85.9 (s), 112.0 (d), 114.7 (d), 118.7 (s), 126.6 (d), 127.2 (d), 127.6 (d), 127.9 (d) Methyl 2-(Bis(4-fluorophenyl)((trimethylsilyl)oxy)methyl)-4-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (3c). Colorless paste (367 mg); R f 0.25 (hexane−ethyl acetate, 5:1); IR (ATR) 1705, 1684, 1603 cm −1 ; 1 H NMR (500 MHz, CDCl 3 ) δ −0.34 (s, 9H), 3.08 (d, 1H, J = 17.8 Hz), 3.17 (dd, 1H, J = 6.9, 17.8 Hz), 3.66 (s, 3H), 5.85 (d, 1H, J = 6.9 Hz), 6.85− 6.90 (m, 2H), 6.95−7.00 (m, 2H), 7.03−7.08 (m, 2H), 7.09− 7.13 (m, 1H), 7.22−7.27 (m, 3H), 7.39−7.44 (m, 1H), 7.76− 7.79 (m, 1H); 13 C NMR (125 Hz, CDCl 3 ) δ 1.2 (q), 40.5 (t), 53.3 (q), 61.2 (d), 84.5 (s), 113.9 (d, J CCF = 21.0 Hz), 114.9 (d, J CCCF = 21.6 Hz), 123.9 (d), 125.2 (d) 13 C NMR (125 Hz, CDCl 3 ) δ 1.3 (q), 37.4 (t), 52.9 (q), 63.0 (d), 76.2 (s), 115.9 (d), 116.5 (d), 122.3 (d), 122.8 (d), 123.4 (d), 123.7 (d), 124.6 (s), 125.1 (s), 125.6 (d), 126.4 (s), 127.3 (d), 128.1 (d), 129.3 (d), 129.4 (d), 133.5 (d) 3.53 (t, 1H, J = 12.9 Hz), 5.25 (d,1H,J = 6.3 Hz),1H),4H),1H),1H),1H),1H),1H),1H),1H); 13 C NMR (125 Hz, CDCl 3 ) δ 1.5 (q), 34.8 (t), 36.4 (t), 38.4 (t), 52.8 (q), 63.1 (d), 89.5 (s), 123.2 (d), 123.8 (d), 124.3 (d), 125.6 (d), 125.9 (d), 126.4 (s), 127.5 (d), 128.2 (d), 129.8 (d), 130.5 (d), 131.9 (d), 133.3 (d), 139.5 (s), 139.8 (s), 140.9 (s), 141.0 (s), 142.8 (s), 154.5 (s), 192.8 (s); HRMS (ESI, ion trap) calcd for C 29 H 32 NO 4 Si (M + H + ) 486.2101, found 486.2081.…”

“…Methyl 4-Oxo-2- (5-((trimethylsilyl)oxy)-5H-dibenzo[a,d]- [7]annulen-5-yl)-3,4-dihydroquinoline-1(2H)-carboxylate (3f). Colorless paste (329 mg); R f 0.25 (hexane−ethyl acetate, 5:1); mp 181−183 °C; IR (ATR) 1717, 1680, 1597 cm −1 ; 1 H NMR (500 MHz, CDCl 3 ) δ −0.07 (s, 9H), 2.32 (d, 1H, J = 18.0 Hz), 2.58 (dd, 1H, J = 7.3, 18.0 Hz), 3.48 (s,3H),5.47 (d,1H,J = 7.3 Hz),6.85 (d,1H, J = 11.9 Hz), 6.94 (d,1H,J = 11.9 Hz),1H),9H),1H),1H); 13 C NMR (125 Hz, CDCl 3 ) δ 2.6 (q), 37.8 (t), 52.7 (q), 55.9 (d), 90.2 (s), 123.6 (d), 124.9 (d), 125.6 (d), 127.0 (d), 127.2 (s), 127.6 (d), 127.8 (d), 127.9 (d), 128.2 (d), 130.1 (d), 130.3 (d), 131.1 (d), 132.9 (s), 133.2 (d), 133.4 (s), 139.5 (s), 140.2 (s), 142.8 (s), 154.5 (s), 193.1 (s); HRMS (ESI, ion trap) calcd for C 29 H 30 NO 4 Si (M + H + ) 484.1944, found 484.1924.…”

“…Benzyl 2-(Diphenyl((trimethylsilyl)oxy)methyl)-4-oxo-3,4dihydroquinoline-1(2H)-carboxylate (3h). White solid (364 mg); R f 0.5 (hexane−ethyl acetate, 5:1); mp 124−126 °C; IR (ATR) 1705, 1688, 1597 cm −1 ; 1 H NMR (500 MHz, CDCl 3 ) δ −0.40 (s, 9H), 2.96−3.16 (m, 2H), 4.90 (d, 1H, J = 12.2 Hz), 5.13 (d,1H,J = 12.2 Hz),5.85 (brs,1H),7H),10H),1H),1H); 13 C NMR (125 Hz, CDCl 3 ) δ 1.3 (q), 40.7 (t), 61.8 (d), 68.0 (t), 86.0 (s), 123.8 (d), 125.2 (brd), 126.1 (d), 126.6 (s), 127.1 (d), 127.4 (d), 127.8 (d), 127.9 (d), 128.0 (d), 128.1 (d), 128.2 (d), 128.3 (d), 128.4 (d), 128.5 (d), 133.0 (d), 135.6 (s), 141.7 (s), 143.3 (s), 154.1 (s), 192.8 (s); HRMS (ESI, ion trap) calcd for C 33 H 34 NO 4 Si (M + H + ) 536.2257, found 536.2249.…”