2,4-dibenzyl-3-sulfanylidene-1,2,4-thiadiazolidin-5-one

• ChemBase ID: 166911
• Molecular Formular: C16H14N2OS2
• Molecular Mass: 314.42516
• Monoisotopic Mass: 314.05475508
• SMILES: c1(=S)n(sc(=O)n1Cc1ccccc1)Cc1ccccc1
• Canonical SMILES: O=c1sn(c(=S)n1Cc1ccccc1)Cc1ccccc1
• InChI: InChI=1S/C16H14N2OS2/c19-16-17(11-13-7-3-1-4-8-13)15(20)18(21-16)12-14-9-5-2-6-10-14/h1-10H,11-12H2
• InChIKey: RUJZRLFQRAMGNM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4-dibenzyl-3-sulfanylidene-1,2,4-thiadiazolidin-5-one
• IUPAC Traditional name: 2,4-dibenzyl-3-sulfanylidene-1,2,4-thiadiazolidin-5-one
• Synonyms: 2,4-Bis(phenylmethyl)-3-thioxo-1,2,4-thiadiazolidin-5-one; GSK-3β Inhibitor III; 2,4-Dibenzyl-5-oxothiadiazolidine-3-thione

Database IDs

• CAS Number: 72966-20-2
• PubChem SID: 162261044
• PubChem CID: 4677904

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.690692
• LogD (pH = 7.4): 4.690692
• Log P: 4.690692
• Molar Refractivity: 91.2882 cm^3
• Polarizability: 35.454 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White to Off-White Solid
• Melting Point: 104-107°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D417960

Glycogen Synthase Kinase-3β is a highly conserved ubiquitously expressed serine/threonine protein kinase involved in signal transduction cascades of multiple cellular processes. An oxothiadiazolidine-3-thione analogue that acts as a non-ATP competitive inhibitor of GSK-3β ( IC50 =10uM).

REFERENCES

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