8-[2-(3-chlorophenyl)ethenyl]-1,3,9-trimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 105641
• Molecular Formular: C16H15ClN4O2
• Molecular Mass: 330.7689
• Monoisotopic Mass: 330.08835342
• SMILES: Cn1c(=O)n(C)c2c(nc(/C=C/c3cccc(Cl)c3)n2C)c1=O
• Canonical SMILES: Clc1cccc(c1)/C=C/c1nc2c(n1C)n(C)c(=O)n(c2=O)C
• InChI: InChI=1S/C16H15ClN4O2/c1-19-12(8-7-10-5-4-6-11(17)9-10)18-13-14(19)20(2)16(23)21(3)15(13)22/h4-9H,1-3H3
• InChIKey: MHYRUZOJQQLLQS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[2-(3-chlorophenyl)ethenyl]-1,3,9-trimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione; 8-[(E)-2-(3-chlorophenyl)ethenyl]-1,3,9-trimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 8-[2-(3-chlorophenyl)ethenyl]-1,3,9-trimethylpurine-2,6-dione; 8-[(E)-2-(3-chlorophenyl)ethenyl]-1,3,9-trimethylpurine-2,6-dione
• Synonyms: 1,3,7-Trimethyl-8-(3-chlorostyryl)xanthine; 8-(3-CHLOROSTYRYL) CAFFEINE; CSC; 8-(3-Chlorostyryl)caffeine

Database IDs

• CAS Number: 147700-11-6
• MDL Number: MFCD00210188
• PubChem SID: 162092154; 24277703
• PubChem CID: 56972151

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.5841928
• LogD (pH = 7.4): 2.5842774
• Log P: 2.5842786
• Molar Refractivity: 88.1832 cm^3
• Polarizability: 32.837006 Å^3
• Polar Surface Area: 58.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: white solid

Safety Information

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

Pharmacology Properties

• Gene Information: human ... ADORA2A(135)mouse ... Maob(109731)rat ... Adora1(29290), Adora2a(25369)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

MP Biomedicals - 02193634

Selective A₂a adenosine receptor antagonist.

Sigma Aldrich - C197

Biochem/physiol Actions
Selective A2A adenosine receptor antagonist.
Caution
Photosensitive, store in the dark

REFERENCES

• Jacobson, et al., J. Med. Chem. , 36 : 1333 (1993).