| Identification | Back Directory | [Name]
2-PYRIMIDINAMINE, 4-(3-CHLOROPHENYL)-N-[4-(TRIFLUOROMETHYL)PHENYL]- | [CAS]
574759-62-9 | [Synonyms]
VAF347
4-(3-Chlorophenyl)-N-[4-(trifluoromethyl)phenyl]pyrimidin-2-amine
2-PYRIMIDINAMINE, 4-(3-CHLOROPHENYL)-N-[4-(TRIFLUOROMETHYL)PHENYL]-
inhibit,Inhibitor,Aryl Hydrocarbon Receptor,VAF 347,AhR,VAF347,VAF-347 | [Molecular Formula]
C17H11ClF3N3 | [MDL Number]
MFCD17010254 | [MOL File]
574759-62-9.mol | [Molecular Weight]
349.74 |
| Chemical Properties | Back Directory | [Boiling point ]
477.8±55.0 °C(Predicted) | [density ]
1.384±0.06 g/cm3(Predicted) | [solubility ]
DMF: 5 mg/ml; DMSO: 1 mg/ml; Ethanol: Slightly soluble | [form ]
A solid | [pka]
2.11±0.10(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
VAF347 is an agonist of the aryl hydrocarbon receptor (AhR).1 It binds to AhR in a radioligand binding assay using guinea pig hepatic cytosol and induces mRNA expression of the AhR target gene CYP1A1 in isolated human peripheral blood mononuclear cells (PBMCs) when used at a concentration of 50 nM. VAF347 (20 μM) inhibits differentiation of HL-60 leukemia cells induced by 1,25-dihydroxy vitamin D3 (calcitriol; ) and promotes differentiation of HL-60 cells induced by all-trans retinoic acid .2 It decreases serum IgE levels and lung and bronchoalveolar lavage fluid (BALF) eosinophil infiltration in an ovalbumin-induced mouse model of allergic inflammation when administered at a dose of 30 mg/kg.3 VAF347 (30 mg/kg) also prevents retinal capillary degeneration in a mouse model of diabetic retinopathy induced by streptozotocin (STZ; ).4 | [References]
1. Lawrence, B.P., Denison, M.S., Novak, H., et al. Activation of the aryl hydrocarbon receptor is essential for mediating the anti-inflammatory effects of a novel low-molecular-weight compound Int. J. Mol. Sci. 112(4),1158-1165(2008).
2. Ibabao, C.N., Bunaciu, R.P., Schaefer, D.M.W., et al. The AhR agonist VAF347 augments retinoic acid-induced differentiation in leukemia cells FEBS Open Bio. 5,308-318(2015).
3. Ettmayer, P., Mayer, P., Kalthoff, F., et al. A novel low molecular weight inhibitor of dendritic cells and B cells blocks allergic inflammation Am. J. Respir. Crit. Care Med. 173(6),599-606(2006).
4. Zapadka, T.E., Lindstrom, S.I., Batoki, J.C., et al. Aryl hydrocarbon receptor agonist VAF347 impedes retinal pathogenesis in diabetic mice Int. J. Mol. Sci. 22(9),4335(2021). |
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