4-benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione

• ChemBase ID: 154405
• Molecular Formular: C10H10N2O2S
• Molecular Mass: 222.2636
• Monoisotopic Mass: 222.04629857
• SMILES: Cn1c(=O)n(c(=O)s1)Cc1ccccc1
• Canonical SMILES: O=c1sn(c(=O)n1Cc1ccccc1)C
• InChI: InChI=1S/C10H10N2O2S/c1-11-9(13)12(10(14)15-11)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
• InChIKey: JDSJDASOXWCHPN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione
• IUPAC Traditional name: 4-benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione
• Synonyms: GSK-3β Inhibitor I, TDZD-8; 4-Benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione; 4-Benzyl-2-methyl-1,2,4-thiadiazolidine-3,5-dione; TDZD-8; TDZD-8

Database IDs

• CAS Number: 327036-89-5
• MDL Number: MFCD04973552
• PubChem SID: 162248544
• PubChem CID: 4124851

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0763493
• LogD (pH = 7.4): 2.0763493
• Log P: 2.0763493
• Molar Refractivity: 58.6847 cm^3
• Polarizability: 22.500483 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; Hexane
• Apperance: white needles; White Solid
• Melting Point: 60-61°C; 63-64.4 °C

Safety Information

• Storage Condition: -20°C Freezer; protect from light
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H334
• GHS Precautionary statements: P261-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: GSK-3

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C10H10N2O2S

DETAILS

Sigma Aldrich - T8325

Biochem/physiol Actions
TDZD-8 is a selective inhibitor of GSK-3, a thiadiazolidinone derivative, non-ATP competitive inhibitor of GSK-3β (IC50 = 2 μM). It does not inhibit Cdk-1/cyclin B, CK-II, PKA or PKC at >100 μM. TDZD-8 has been proposed to bind to the kinase site of GSK-3β.

Toronto Research Chemicals - B285725

Glycogen Synthase Kinase-3β is a highly conserved ubiquitously expressed serine/threonine protein kinase involved in signal transduction cascades of multiple cellular processes. TDZD-8 is a thiadiazolidinone (TDZD) analogue that acts as a highly selectiv

REFERENCES

• Martinez, A., et al.: J. Med. Chem., 45, 1292 (2002)