ChemicalBook--->CAS DataBase List--->1211-19-4

1211-19-4

1211-19-4 Structure

1211-19-4 Structure
IdentificationBack Directory
[Name]

BenzaMide, 2-(phenylaMino)-
[CAS]

1211-19-4
[Synonyms]

SIRT-IN-3
2-anilinobenzamide
2-(Phenylamino)benzamide
BenzaMide, 2-(phenylaMino)-
[Molecular Formula]

C13H12N2O
[MDL Number]

MFCD00476529
[MOL File]

1211-19-4.mol
[Molecular Weight]

212.25
Chemical PropertiesBack Directory
[Melting point ]

122 °C
[Boiling point ]

413.3±28.0 °C(Predicted)
[density ]

1.218±0.06 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[solubility ]

DMSO: 250 mg/mL (1177.86 mM)
[form ]

Solid
[pka]

15.59±0.50(Predicted)
[color ]

White to yellow
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Uses]

SIRT-IN-3 is a potent SIRT inhibitor, with an IC50 of 17 μM for SIRT1. SIRT-IN-3 shows about 4-fold and 14-fold selectivity for SIRT1 over SIRT2 and SIRT3, respectively (IC50 of 74 μM and 235 μM for SIRT2 and SIRT3, respectively)[1].
[Synthesis]

2-IODOBENZAMIDE

3930-83-4

Aniline

62-53-3

BenzaMide, 2-(phenylaMino)-

1211-19-4

2-Iodobenzamide (0.5 mmol, 124 mg), aniline or α-substituted benzylamine (1.0 mmol), potassium carbonate (1.0 mmol, 138 mg), and copper bromide (0.05 mmol, 11 mg) were dissolved in dimethylsulfoxide (5 mL) in a two-necked, round-bottomed flask fitted with a magnetic stirrer under argon protection. The reaction mixture was stirred at 110 °C for 4 hours. After completion of the reaction, the reaction mixture was concentrated using a rotary evaporator. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (2:1, v/v) to afford the target product 2-(phenylamino)benzamide.

[References]

[1] Suzuki T, et al. 2-Anilinobenzamides as SIRT inhibitors. ChemMedChem. 2006 Oct;1(10):1059-62. DOI:10.1002/cmdc.200600162
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