BenzenesulfonaMide, 5-(phenylsulfonyl)-N-4-piperidinyl-2-(trifluoroMethyl)- Chemical Properties

Boiling point:

601.1±65.0 °C(Predicted)

Density 

1.50±0.1 g/cm3(Predicted)

solubility 

DMF: 3 mg/ml; DMSO: 3 mg/ml; DMSO:PBS (pH 7.2) (1:10): 0.1 mg/ml

pka

8.76±0.20(Predicted)

form 

Powder

color 

White to off-white

InChI

InChI=1S/C18H19F3N2O4S2/c19-18(20,21)16-7-6-15(28(24,25)14-4-2-1-3-5-14)12-17(16)29(26,27)23-13-8-10-22-11-9-13/h1-7,12-13,22-23H,8-11H2

InChIKey

ITBGJNVZJBVPLJ-UHFFFAOYSA-N

SMILES

C1(S(NC2CCNCC2)(=O)=O)=CC(S(C2=CC=CC=C2)(=O)=O)=CC=C1C(F)(F)F

BenzenesulfonaMide, 5-(phenylsulfonyl)-N-4-piperidinyl-2-(trifluoroMethyl)- Usage And Synthesis

Description

WAY-316606 is an inhibitor of secreted frizzled-related protein 1 (sFRP-1; IC₅₀ = 0.5 μM). It increases Wnt signaling in U2OS osteosarcoma cells (EC₅₀ = 0.65 μM). WAY-316606 increases total bone area in a murine calvarial organ culture assay when used at concentrations greater than 0.1 nM.

Uses

WAY 316606 is an inhibitor of the secreted protein sFRP-1, an endogenous antagonist of the secreted glycoprotein Wnt. The affinity of WAY-316606 for sFRP-1 is determined using the FP binding assay with IC50 of 0.5 μM[1].

Definition

ChEBI: WAY-316606 is a sulfonamide resulting from the formal condensation of the sulfonic acid group of 5-(phenylsulfonyl)-2-(trifluoromethyl)benzenesulfonic acid with the primary amino group of piperidin-4-amine. An inhibitor of secreted Frizzled-Related Protein-1 (sFRP-1). It has a role as a secreted frizzled-related protein 1 inhibitor. It is a sulfone, a sulfonamide, a member of (trifluoromethyl)benzenes, a member of piperidines and a secondary amino compound.

in vivo

References

[1] Moore, WJ, et al. Modulation of Wnt Signaling Through Inhibition of Secreted Frizzled-Related Protein I (sFRP-1) with N-Substituted Piperidinyl Diphenylsulfonyl Sulfonamides. Journal of Medicinal Chemistry (2009), 52(1), 105-116. DOI:10.1021/jm801144h
[2] Bodine PV, et al. A small molecule inhibitor of the Wnt antagonist secreted frizzled-related protein-1 stimulates bone formation. Bone. 2009 Jun;44(6):1063-8. DOI:10.1016/j.bone.2009.02.013

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