5-({4-[2-(4-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

• ChemBase ID: 153242
• Molecular Formular: C20H18N2O5S
• Molecular Mass: 398.43232
• Monoisotopic Mass: 398.09364269
• SMILES: c1ccc2c(c1)C(=O)N(CO2)CCOc1ccc(cc1)CC1C(=O)NC(=O)S1
• Canonical SMILES: O=C1NC(=O)C(S1)Cc1ccc(cc1)OCCN1COc2c(C1=O)cccc2
• InChI: InChI=1S/C20H18N2O5S/c23-18-17(28-20(25)21-18)11-13-5-7-14(8-6-13)26-10-9-22-12-27-16-4-2-1-3-15(16)19(22)24/h1-8,17H,9-12H2,(H,21,23,25)
• InChIKey: RFMNEXVCPAPDRA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-({4-[2-(4-oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• IUPAC Traditional name: 5-({4-[2-(4-oxo-2H-1,3-benzoxazin-3-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[[4-[2-(4-Oxo-2H-1,3-benzoxazin3(4H)-yl)ethoxy]phenyl]methyl2,4-thiazolidinedione; DRF 2519

Database IDs

• MDL Number: MFCD06798336
• PubChem SID: 162247381; 24894036
• PubChem CID: 9908833

CALCULATED PROPERTIES

• Acid pKa: 7.6135864
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.6669805
• LogD (pH = 7.4): 2.4660544
• Log P: 2.670273
• Molar Refractivity: 103.3802 cm^3
• Polarizability: 39.98293 Å^3
• Polar Surface Area: 84.94 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white solid

Safety Information

• Storage Condition: under inert gas
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H18N2O5S

DETAILS

Sigma Aldrich - D6567

Biochem/physiol Actions
DRF-2519 is a dual PPARα/γ activator. DRF-2519 has better reduction of plasma insulin, triglyceride, and free fatty acid levels than those treated with rosiglitazone.