Design, synthesis, biological evaluation, and molecular docking study of thioxo-2,3-dihydroquinazolinone derivative as tyrosinase inhibitors

Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles

“…3-Phenylquinazoline-2,4(1H,3H)-dione (2a). 59 The title compound was synthesized according to the general procedure and obtained as a white solid (40.5 mg, 85%); 3:7 (EA/ Hexane) as the eluent; 3-(p-Tolyl)quinazoline-2,4(1H,3H)-dione (2b). 59 The title compound was synthesized according to the general procedure and obtained as a white solid (35.3 mg, 70%); 3:7 (EA/Hexane) as the eluent; 1 H-NMR (400 MHz, DMSO-d 6 ) 11.52 (s, 1H), 7.93 (dd, J = 8.0 Hz, 1.4 Hz, 1H), 7.69 (td, J = 8.0 Hz, 1.2 Hz, 1H), 7.28−7.17 (m, 6H), 2.37 (s, 3H); 13 3-(4-Ethylphenyl)quinazoline-2,4(1H,3H)-dione (2c).…”

“…59 The title compound was synthesized according to the general procedure and obtained as a white solid (40.5 mg, 85%); 3:7 (EA/ Hexane) as the eluent; 3-(p-Tolyl)quinazoline-2,4(1H,3H)-dione (2b). 59 The title compound was synthesized according to the general procedure and obtained as a white solid (35.3 mg, 70%); 3:7 (EA/Hexane) as the eluent; 1 H-NMR (400 MHz, DMSO-d 6 ) 11.52 (s, 1H), 7.93 (dd, J = 8.0 Hz, 1.4 Hz, 1H), 7.69 (td, J = 8.0 Hz, 1.2 Hz, 1H), 7.28−7.17 (m, 6H), 2.37 (s, 3H); 13 3-(4-Ethylphenyl)quinazoline-2,4(1H,3H)-dione (2c). 60 The title compound was synthesized according to the general procedure and obtained as a white solid (35.6 mg, 67%); 3:7 (EA/Hexane) as the eluent; 1 H-NMR (400 MHz, DMSO-d 6 ) δ 11.53 (s, 1H), 7.94 (dd, J = 8.0 Hz, 1.6 Hz, 1H), 7.70 (td, J = 8.0 Hz, 1.2 Hz, 1H), 7.33−7.30 (m, 2H), 7.25−7.19 (m, 4H), 2.67 (q, J = 8.0 Hz, 2H), 1.24 (t, J = 8.0 Hz, 3H).…”

“…13 3-(4-Methoxyphenyl)quinazoline-2,4(1H,3H)-dione (2d). 59 The title compound was synthesized according to the general procedure and obtained as a white solid (45 mg, 73%); 3:7 (EA/Hexane) as the eluent; 1 H-NMR (400 MHz, DMSO-d 6 ) δ 11.50 (s, 1H), 7.93 (dd, J = 8.0 Hz, 1.2 Hz, 1H), 7.69 (td, J = 8.0 Hz, 1.6 Hz, 1H), 7.23−7.20 (m, 4H), 7.03−6.99 (m, 2H), 3.81 (s, 3H); 13 3-(2,5-Dimethoxyphenyl)quinazoline-2,4(1H,3H)-dione (2e). 61 The title compound was synthesized according to the general procedure and obtained as a white solid (39 mg, 75%); 3:7 (EA/ Hexane) as the eluent; 1 H-NMR (400 MHz, DMSO-d 6 ) δ 11.48 (s, Table 3.…”

Rational Design, Synthesis, in Vitro, and in Silico Studies of Chlorophenylquinazolin‐4(3H)‐One Containing Different Aryl Acetohydrazides as Tyrosinase Inhibitors

“…Noteworthy the antibacterial activity of tyrosinase inhibitors were also confirmed in recent studies. [12] Lots of efforts have been made to discover new chemical pharmacophores that inhibit tyrosinase enzyme to reduce mentioned undesirable impacts with fewer side effects including polyphenol and flavonoids, [13] phenylpropanoids, [14] thioamides, and thioureas, [15] azine, [16] hydrazine, [17] thiosemicarbazide [18] piperazine, [19] benzothiazole, [20] salicylaldehyde bearing bis(sulfonate) [21] as well as quinazolines and quinazolinone [9,22] based derivatives.…”

Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents

“…Quinazoline as nitrogen-containing heterocyclic compound is synthesized in the structure of many synthetic compounds using different synthetic methods including aza-diels–alder reaction, aza-wittig reaction, metal-mediated reaction, and oxidative cyclization [ 8 – 12 ]. Quinazoline scaffold show diverse biologically and pharmacologically active anti-cancer [ 13 ], analgesic [ 14 ], anti-tuberculosis [ 15 ], antihypertensive [ 16 ], anti-diabetes [ 17 ] anti-melanogenesis [ 18 , 19 ], anti-urease [ 20 ], antifungal [ 21 ], and antibacterial [ 22 , 23 ] agents. Quinazolinone is a naturally occurring alkaloid that can be found in many natural products with diverse biological activities [ 24 – 26 ].…”