| Identification | Back Directory | [Name]
2-Methyl-5-[3-[4-(methylsulfinyl)phenyl]-5-benzofuranyl]-1,3,4-oxadiazole | [CAS]
1005201-24-0 | [Synonyms]
TCS 2002
2-Methyl-5-[3-[4-(methylsulfinyl)phenyl]-5-benzofuranyl]-1,3,4-oxadiazole
2-methyl-5-[3-(4-methylsulfinylphenyl)-1-benzofuran-5-yl]-1,3,4-oxadiazole
1,3,4-Oxadiazole, 2-Methyl-5-[3-[4-(Methylsulfinyl)phenyl]-5-benzofuranyl]- | [Molecular Formula]
C18H14N2O3S | [MDL Number]
MFCD15528930 | [MOL File]
1005201-24-0.mol | [Molecular Weight]
338.38 |
| Chemical Properties | Back Directory | [Boiling point ]
579.0±60.0 °C(Predicted) | [density ]
1.43±0.1 g/cm3(Predicted) | [storage temp. ]
Store at +4°C | [solubility ]
<33.84mg/ml in DMSO; <8.46mg/ml in ethanol | [form ]
solid | [pka]
-4.23±0.34(Predicted) | [color ]
White | [InChI]
1S/C18H14N2O3S/c1-11-19-20-18(23-11)13-5-8-17-15(9-13)16(10-22-17)12-3-6-14(7-4-12)24(2)21/h3-10H,1-2H3 | [InChIKey]
RCKYSTKYIVULEK-UHFFFAOYSA-N | [SMILES]
CS(C(C=C1)=CC=C1C2=COC3=C2C=C(C4=NN=C(C)O4)C=C3)=O |
| Hazard Information | Back Directory | [Uses]
TCS 2002 is a Wnt/β-catenin signaling modulator, which is associated with diseases such as cancer and Alzheimer’s diasease. | [Biological Activity]
tcs 2002 is a potent inhibitor of gsk-3β with ic50 value of 35 nm [1].glycogen synthase kinase 3 (gsk-3) is a serine/threonine protein kinase and functions by phosphorylating a serine or threonine residue on its target protein. gsk3β plays an important role in neuronal cell development, energy metabolism and body pattern formation.tcs 2002 is a potent gsk -3β inhibitor with ic50 value of 35 nm. (s) -tcs 2002 and (r) -tcs 2002 inhibited gsk-3β with ic50 values of 34 and 140 nm, respectively. tcs 2002 exhibited good bioavailability (f=40%) and solubility (38 μg/ml). (s) -tcs 2002 showed no inhibitory activity against 12 tyrosine kinases and 10 serine/threonine kinases up to 10 μm, indicating that (s) -tcs 2002 was a highly selective gsk -3β inhibitor [1].in mice, cold water stress (cws) induced tau hyperphosphorylation at several gsk -3β directed sites such as s199, thr205, thr231 and ser396. (s) -tcs 2002 significantly inhibited tau phosphorylation by 35% [1]. | [in vivo]
TCS2002 (Compound 9b) (1-3 mg/kg;1-24 hours; GS rats andC57BL/6N mice) exhibits good pharmacokinetic profiles and favor able BBB permeability with AUC0-24h value is 734 ng h/g and Kp value (ratio of brain and plasma) is 1.6[1]. | Animal Model: | IGS rats (male, 8 weeks old)[1] | | Dosage: | 1 and 3mg/kg | | Administration: | Intravenous injection and oral administration;for 1, 2, 4, 8, 24 hours. | | Result: | 1.19| comp | (S)-9b | (S)-9c | | VDSS,iv (mL/kg) | 1134 | 1650 | | CLtotal,iv (mL/min/kg) | 27.4 | 28.4 | | Cmax,po (ng/mL) | 396.9 | 289.6 | | AUC0-24 h,po (ng·h/mL) | 1380.6 | 1229.1 | | MRTpo (h) | 2.19 | 3.03 | | Fd (%) | 72.8 | 65.5 |
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| [IC 50]
GSK-3: 35 nM (IC50) | [storage]
Store at +4°C | [References]
[1]. saitoh m, kunitomo j, kimura e, et al. 2-{3-[4-(alkylsulfinyl)phenyl]-1-benzofuran-5-yl}-5-methyl-1,3,4-oxadiazole derivatives as novel inhibitors of glycogen synthase kinase-3beta with good brain permeability. j med chem, 2009, 52(20): 6270-6286. |
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| Company Name: |
Merck KGaA
|
| Tel: |
21-20338288 |
| Website: |
www.sigmaaldrich.cn |
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