1-[(4-methoxyphenyl)methyl]-3-(5-nitro-1,3-thiazol-2-yl)urea

• ChemBase ID: 1717
• Molecular Formular: C12H12N4O4S
• Molecular Mass: 308.31308
• Monoisotopic Mass: 308.05792588
• SMILES: c1(sc(cn1)[N+](=O)[O-])NC(=O)NCc1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)CNC(=O)Nc1ncc(s1)[N+](=O)[O-]
• InChI: InChI=1S/C12H12N4O4S/c1-20-9-4-2-8(3-5-9)6-13-11(17)15-12-14-7-10(21-12)16(18)19/h2-5,7H,6H2,1H3,(H2,13,14,15,17)
• InChIKey: YAEMHJKFIIIULI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(4-methoxyphenyl)methyl]-3-(5-nitro-1,3-thiazol-2-yl)urea
• IUPAC Traditional name: 1-[(4-methoxyphenyl)methyl]-3-(5-nitro-1,3-thiazol-2-yl)urea
• Synonyms: GSK-3β Inhibitor VIII; AR-A014418; N-[(4-Methoxyphenyl)methyl]-N'-(5-nitro-2-thiazolyl)urea; AR 0133418; GSK 3B Inhibitor VIII; AR-AO 14418; N-(4-Methoxybenzyl)-N′-(5-nitro-1,3-thiazol-2-yl)urea; AR-A014418; N-(4-Methoxybenzyl)-N'-(5-Nitro-1,3-Thiazol-2-Yl)Urea

Database IDs

• CAS Number: 487021-52-3
• MDL Number: MFCD08277040
• PubChem SID: 46507570; 160965173
• PubChem CID: 448014

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.321312
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.1169052
• LogD (pH = 7.4): 2.1164172
• Log P: 2.1169114
• Molar Refractivity: 75.7323 cm^3
• Polarizability: 28.31739 Å^3
• Polar Surface Area: 106.39 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.05
• LOG S: -4.41
• Solubility (Water): 1.19e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥20 mg/mL, clear, light yellow; H2O: insoluble; Methanol
• Apperance: off-white to tan solid; Pale Yellow Solid
• Melting Point: 208-210°C (dec.)

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41
• Safety Statements: 26-36/39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: GSK-3

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H12N4O4S

DETAILS

DrugBank - DB01950

Drug information: experimental

Sigma Aldrich - A3230

Biochem/physiol Actions
Glycogen synthase kinase 3 (GSK3) is a serine/threonine kinase that has been implicated in pathological conditions such as diabetes and Alzheimer′s disease. GSK3 inhibitor, AR-A014418, inhibits GSK3 (IC50 = 104 nM), in an ATP-competitive manner (Ki = 38 nM). AR-A014418 does not significantly inhibit cdk2 or cdk5 (IC50 > 100 μM) or 26 other kinases, demonstrating high specificity for GSK3.

Toronto Research Chemicals - A765500

Glycogen Synthase Kinase 3β (GSK-3β) inhibitor.

REFERENCES

• Koh, S., et al.:Toxicol., 247, 112 (2008)
• Vadivelan, S., et al.: Eur. J. Med. Chem., 44, 2361 (2008)
• Min, W., et al.: Neuropharmacol., 56, 463 (2008)