| Identification | Back Directory | [Name]
Tacedinaline | [CAS]
112522-64-2 | [Synonyms]
CI 994
CS-617
Cl-994
Goe 5549
PD 123654
CI994, >=99%
Tacedinaline
acetyldinaline
N-Acetyldinaline
CI994 (Tacedinaline)
Tacedinaline (CI994)
Tacedinaline USP/EP/BP
4-Acetylamino-N-(2'
-aminophenyl)benzamide
PD-123654;CI-994;PD123654
CI-994 (Acetyldinaline,PD123654)
CI 994 - PD 123654 | Tacedinaline
Cl-994(Tacedinalin,N-Acetyldinalin)
4-AcetaMido-N-(2-aMinophenyl)benzaMide
4-acetylamino-n-(2'-aminophenyl)benzamide
4-Acetamido-N-(2-aminophenyl)benzamide >
4-Acetylamino-N-(2'-aminophenyl)benzamide
Benzamide, 4-(acetylamino)-N-(2-aminophenyl)-
CI-994 4-Acetylamino-N-(2'-aminophenyl)benzamide | [EINECS(EC#)]
200-256-5 | [Molecular Formula]
C15H15N3O2 | [MDL Number]
MFCD00866266 | [MOL File]
112522-64-2.mol | [Molecular Weight]
269.3 |
| Chemical Properties | Back Directory | [Melting point ]
216.1 °C | [Boiling point ]
450.6±30.0 °C(Predicted) | [density ]
1.322±0.06 g/cm3(Predicted) | [RTECS ]
CU8702023 | [storage temp. ]
Store at +4°C | [solubility ]
Soluble in DMSO | [form ]
powder | [pka]
13.15±0.70(Predicted) | [color ]
off-white | [Sensitive ]
Air Sensitive | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. | [InChIKey]
VAZAPHZUAVEOMC-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [Description]
CI-994 (112522-64-2) is an orally active histone deacetylase (HDAC) inhibitor, IC50 = 0.9, 0.9, 1.2 and >20 μM for HDAC1, HDAC2, HDAC3 and HDAC8 respectively.1 Mediates G1 cell cycle arrest, inhibits proliferation and induces apoptosis in vitro and in vivo.2,3 Increases neuroplasticity during memory extinction.4 Protects beta cells from cytokine-induced apoptosis.4 | [Uses]
Tacedinaline is a histone deacetylase (HDAC) inhibitor. Tacedinaline is an anti-cancer agent as HDAC inhibitors block angiogenesis, arrest cell growth, and lead to differentiation and apoptosis in tum
or cells. Studies show Tacedinaline to be effective against acute myeloid leukemia in vitro and in vivo when used in combination with conventional anti-cancer agents. | [Definition]
ChEBI: A benzamide obtained by formal condensation of the carboxy group of 4-acetamidobenzoic acid with one of the amino groups of 1,2-phenylenediamine. An oral cytostatic drug with impressive differential activity against leukemic cells and normal stem-cells. Al
o used in combination therapy for selected tumors including non-smoll cell lung, pancreatic, breast, and colorectal cancers. | [Biological Activity]
Orally active histone deacetylase (HDAC) inhibitor (K i values are 0.41, 0.75, >100 and >100 μ M for HDAC1, HDAC3, HDAC6 and HDAC8 respectively). Mediates G 1 cell cycle arrest, inhibits proliferation and induces apoptosis in vitro and in vivo . | [Synthesis]
GENERAL STEPS: Trifluoroacetic acid (22 mL) was added slowly and dropwise to a solution of tert-butyl (2-(4-acetylaminobenzoyl)phenyl)carbamate 1.5 (3.5 g, 9.5 mmol) in anhydrous dichloromethane (55 mL) at 0 °C. The reaction mixture was slowly warmed to 23 °C and stirred at this temperature for 2 h until the reaction was complete. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was diluted with water and the pH was adjusted with saturated aqueous sodium bicarbonate to about 8. The precipitate precipitated was filtered, washed sequentially with water and ether, and finally dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 1.6 as an off-white solid in a yield of 2.4 g (96% yield).1H NMR (500 MHz, d6-DMSO) δ 10.18 (s, 1H), 9.54 (s, 1H), 7.93 (d, J = 8.5Hz, 2H), 7.69 (d, J = 8.5Hz, 2H), 7.15 (d, J = 7.5Hz, 1H), 6.96 (t, J = 7.5Hz, 1H), 6.78 (d, J = 7.5Hz, 1H), 6.59 (t, J = 7.5Hz, 1H ), 4.88 (s, 2H), 2.08 (s, 3H).MS (ESI+): m/z 269.9 [M + H]+. | [target]
HDAC1 | [storage]
+4°C | [References]
1) Moradei et al. (2007), Novel aminophenyl benzamide-type histone deacetylase inhibitors with enhanced potency and selectivity; J. Med. Chem., 50 5543
2) Beckers et al. (2007), Distinct pharmacological properties of second generation HDAC inhibitors with the benzamide or hydroxamate head group; Int. J. Cancer, 121 1138
3) Loprevite et al. (2005), In vitro study of CI-994, a histone deacetylase inhibitor, in non-small cell lung cancer cell lines; Oncol. Res., 15 39
4) Chou et al. (2012), Inhibition of histone deacetylase 3 protects beta cells from cytokine-induced apoptosis; Chem. Biol., 19 669 |
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