1,3-diethyl-8-phenyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 153215
• Molecular Formular: C15H16N4O2
• Molecular Mass: 284.31314
• Monoisotopic Mass: 284.12732577
• SMILES: CCn1c2c(c(=O)n(c1=O)CC)[nH]c(n2)c1ccccc1
• Canonical SMILES: CCn1c2nc([nH]c2c(=O)n(c1=O)CC)c1ccccc1
• InChI: InChI=1S/C15H16N4O2/c1-3-18-13-11(14(20)19(4-2)15(18)21)16-12(17-13)10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3,(H,16,17)
• InChIKey: LVSWNSHUTPWCNF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl-8-phenyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 1,3-diethyl-8-phenylxanthine
• Synonyms: 1,3-Diethyl-3,9-dihydro-8-phenyl-1H-purine-2,6-dione; 8-Phenyl-1,3-diethylxanthine; 1,3-Diethyl-8-phenylxanthine; DPX; 1,3-Diethyl-8-phenylxanthine

Database IDs

• CAS Number: 75922-48-4
• MDL Number: MFCD00043206
• PubChem SID: 162247354
• PubChem CID: 1328

CALCULATED PROPERTIES

• Acid pKa: 7.1532016
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9606999
• LogD (pH = 7.4): 1.6123754
• Log P: 1.9690645
• Molar Refractivity: 89.5333 cm^3
• Polarizability: 29.935568 Å^3
• Polar Surface Area: 69.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; ethanol: soluble; H2O: very slightly soluble; Water (sparingly)
• Apperance: Off-White to Pale Yellow Solid; white solid
• Melting Point: 298-300°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADORA1(134)

Product Information

• Empirical Formula (Hill Notation): C15H16N4O2

DETAILS

Sigma Aldrich - A003

Biochem/physiol Actions
A1 Adenosine receptor antagonist

Toronto Research Chemicals - D444700

A selective A1 adenosine receptor antagonist. Binding activity: IC50 (nM): A1 =135, A2 = 5300. UV lmax (log e, MeOH): 237 nm (4.35), 309 nm (4.33).

REFERENCES

• Proc. Natl. Acad. Sci. USA, 77, 5547 (1980)
• Proc. Natl. Acad. Sci. USA, 78, 3260 (1981)