1-(4-AMino-phenyl)-3-(4-tert-butyl-benzoyl)-thiourea

Tenovin-3 is able to increase p53 levels, determined in MCF-7 cells treated for 6 hr at 10 μM.Target: p53in vitro: Tenovins inhibit the activities of human SirT1 and SirT2, two members of the NAD+-dependent class III histone deacetylases that also belong to the sirtuin family.[1]

To a stirred solution of 4-tert-butylbenzoyl chloride (10 iranol, 1.97 g) in acetone (20 mL) under argon atmosphere was added sodium thiocyanate (10 mol, 0.81 g) . After 2 h this mixture was added dropwise to a solution of 1, 4- phenylenediamine (20 mmol, 2.1βg) in acetone (50 mL) under argon that was cooled to 0 °C. After warming to ambient temperature the reaction mixture was stirred for 36 h. The mixture was concentrated in vacuo to a residue that was taken up into dichloromethane, filtered and the filtrate was concentrated and chromatographed on a silica gel column, eluting with ethyl acetate - petroleum ether mixture. Trituration of the resultant solid with diethyl ether provided analytically pure material, 2.45g (75percent). Analysis provided the following data: mpt 189-191 °C; To a solution of 4 (4.0 g, 20.4 mmol) in acetone (30 mL) was added sodium thiocyanate (1.7 g, 20.8 mmol). The resulting pale yellow suspension was stirred at rt for 8 h, then added to a solution of 1, 4-phenylenediamine (4.4 g, 40.8 mmol) in acetone (30 mL) at 0 °C. The brown suspension was warmed to rt and stirred for 16 h. The solvent was concentrated in vacuo and the remaining residue resuspended in CH

Molecular Weight:327.4
XLogP3:4.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:327.14053348
Monoisotopic Mass:327.14053348
Topological Polar Surface Area:99.2
Heavy Atom Count:23
Complexity:417
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes