3-(2-aminoethyl)-5-[(4-ethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione hydrochloride

• ChemBase ID: 153893
• Molecular Formular: C14H17ClN2O3S
• Molecular Mass: 328.81438
• Monoisotopic Mass: 328.06484109
• SMILES: CCOc1ccc(cc1)/C=C\1/C(=O)N(C(=O)S1)CCN.Cl
• Canonical SMILES: NCCN1C(=O)S/C(=C\c2ccc(cc2)OCC)/C1=O.Cl
• InChI: InChI=1S/C14H16N2O3S.ClH/c1-2-19-11-5-3-10(4-6-11)9-12-13(17)16(8-7-15)14(18)20-12;/h3-6,9H,2,7-8,15H2,1H3;1H
• InChIKey: PQVLWVGMXJPJLG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-aminoethyl)-5-[(4-ethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione hydrochloride
• IUPAC Traditional name: 3-(2-aminoethyl)-5-[(4-ethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione hydrochloride
• Synonyms: Erk Inhibitor; 3-(2-Aminoethyl)-5-((4-ethoxyphenyl)methylene)-2,4-thiazolidinedione hydrochloride

Database IDs

• CAS Number: 294675-79-9(freebase)
• MDL Number: MFCD09038681
• PubChem SID: 24891079; 162248032
• PubChem CID: 16760416

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.4612042
• LogD (pH = 7.4): -0.24918012
• Log P: 1.4757879
• Molar Refractivity: 80.2793 cm^3
• Polarizability: 30.764532 Å^3
• Polar Surface Area: 72.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥4 mg/mL
• Apperance: off-white powder

Safety Information

• Storage Condition: desiccated; under inert gas
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H16N2O3S · HCl

DETAILS

Sigma Aldrich - A6355

Application
3-(2-Aminoethyl)-5-((4-ethoxyphenyl)methylene)-2,4-thiazolidinedione is an extracellular signal-regulated kinase (ERK) docking domain inhibitor. ERK inhibitors have been used to study traumatic brain injuries.
Biochem/physiol Actions
3-(2-Aminoethyl)-5-((4-ethoxyphenyl)methylene)-2,4-thiazolidinedione is extracellular signal-regulated kinase (ERK) docking domain inhibitor. Inhibits ERK binding rather then ERK activity at the ATP domain. IC50 = 25 μM in HeLa, A549, and SUM-159 tumor cells. Currently, no specific inhibitors of the ERK proteins exist. Preferentially binds to ERK2 with a Kd of ~5 μM and prevents its interaction with protein substrates. Shown to block ERK-mediated phosphorylation of ribosomal S6 kinase-1 (RSK-1) and ternary complex factor Elk-1, but exhibits little effect on ERK1/2 phosphorylation by MEK1/2.