5-{[4-(ethylsulfanyl)phenyl]methylidene}imidazolidine-2,4-dione

• ChemBase ID: 154505
• Molecular Formular: C12H12N2O2S
• Molecular Mass: 248.30088
• Monoisotopic Mass: 248.06194863
• SMILES: CCSc1ccc(cc1)/C=C/1\C(=O)NC(=O)N1
• Canonical SMILES: CCSc1ccc(cc1)/C=C\1/NC(=O)NC1=O
• InChI: InChI=1S/C12H12N2O2S/c1-2-17-9-5-3-8(4-6-9)7-10-11(15)14-12(16)13-10/h3-7H,2H2,1H3,(H2,13,14,15,16)
• InChIKey: UWMDBDYLNJITCD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[4-(ethylsulfanyl)phenyl]methylidene}imidazolidine-2,4-dione
• IUPAC Traditional name: 5-{[4-(ethylsulfanyl)phenyl]methylidene}imidazolidine-2,4-dione
• Synonyms: (Z)-5-(4-(ethylthio)benzylidene)-hydantoin; (Z)-5-[4-(Ethylthio)benzylidene]imidazolidine-2,4-dione; 5-(4-Ethylsulfanylbenzylidene)imidazolidine-2,4-dione; S-PMH

Database IDs

• MDL Number: MFCD12912441
• PubChem SID: 162248644
• PubChem CID: 71311882

CALCULATED PROPERTIES

• Acid pKa: 8.229958
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.5579511
• LogD (pH = 7.4): 1.4995682
• Log P: 1.5587499
• Molar Refractivity: 69.2842 cm^3
• Polarizability: 25.942923 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H12N2O2S

DETAILS

Sigma Aldrich - S0826

Biochem/physiol Actions
S-PMH augments cell-cell adhesion by enhancing tight and adherens junctions (TJ and AJ) and by abolishing the destabilizing actions of Calcitonin (CT) on these complexes. Calcitonin and its receptor are expressed in prostate cell cancers and plays a pivotal role in metastasis and tumorgenesis. It appears that CT promotes prostate cancer metastasis by reducing cell-cell adhesion through the disassembly of tight and adherens junctions and activation of B-catenin signaling. S-PMH apparently blocks CT-stimulated alphavbeta3 activity (a key factor in bone metastasis). In a nude mice model I.p. administered S-PMH and its S-ethyl derivative decreased orthotopic tumor growth and inhibited the formation of tumor micrometastases in distant organs. S-PMH is relatively nontoxic in a cell proliferation assay.