3-[7-(2-chlorophenyl)-13-methyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaen-4-yl]-1-[(2H8)morpholin-4-yl]propan-1-one

• ChemBase ID: 160749
• Molecular Formular: C22H22ClN5O2S
• Molecular Mass: 455.96038
• Monoisotopic Mass: 455.11827365
• SMILES: c1(CCC(=O)N2CCOCC2)sc2c(c1)C(=NCc1n2c(nn1)C)c1ccccc1Cl
• Canonical SMILES: O=C(N1CCOCC1)CCc1sc2c(c1)C(=NCc1n2c(C)nn1)c1ccccc1Cl
• InChI: InChI=1S/C22H22ClN5O2S/c1-14-25-26-19-13-24-21(16-4-2-3-5-18(16)23)17-12-15(31-22(17)28(14)19)6-7-20(29)27-8-10-30-11-9-27/h2-5,12H,6-11,13H2,1H3
• InChIKey: JGPJQFOROWSRRS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[7-(2-chlorophenyl)-13-methyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0^2,^6]trideca-2(6),4,7,10,12-pentaen-4-yl]-1-[(^2H₈)morpholin-4-yl]propan-1-one
• IUPAC Traditional name: 3-[7-(2-chlorophenyl)-13-methyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0^2,^6]trideca-2(6),4,7,10,12-pentaen-4-yl]-1-[(^2H₈)morpholin-4-yl]propan-1-one
• Synonyms: trans-4-[3-[6-Amino-9-[N-(ethyl-d5)-β-D-ribofuranuronamidosyl)]-9H-purin-2-yl]-2-propyn-1-yl]-cyclohexanecarboxylic Acid Methyl Ester; ATL 146e-d5; BMS 068645-d5; DWH 146e-d5; Apadenoson-d5

Database IDs

• PubChem SID: 162254884
• PubChem CID: 46780465

CALCULATED PROPERTIES

• Acid pKa: 18.49283
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.3856792
• LogD (pH = 7.4): 1.4333571
• Log P: 1.434
• Molar Refractivity: 131.6815 cm^3
• Polarizability: 45.541256 Å^3
• Polar Surface Area: 72.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 183-188°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A710502

An A2A adenosine receptor agonist. Adjunct to nuclear myocardial perfusion imaging in patients unable to exercise adequately.

REFERENCES

• Bolli, R., et al.: Cardiovasc. Res., 27, 728 (1993)
• Bolli, R., et al.: J. Clin. Invest., 96, 1066 (1993)
• Jordan, J., et al.: J. Pharmacol. Exp. Ther., 280, 301 (1993)
• Rieger, J., et al.: J. Med. Chem., 44, 531 (1993)
• Singh, M., et al.: J. Cardiovasc.