(3aR,4S,6R)-6-(6-amino-9H-purin-9-yl)-N-ethyl-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxole-4-carboxamide

• ChemBase ID: 168463
• Molecular Formular: C15H20N6O4
• Molecular Mass: 348.3571
• Monoisotopic Mass: 348.15460315
• SMILES: n1cnc2c(c1N)ncn2[C@H]1C2[C@H]([C@H](O1)C(=O)NCC)OC(O2)(C)C
• Canonical SMILES: CCNC(=O)[C@H]1O[C@H](C2[C@H]1OC(O2)(C)C)n1cnc2c1ncnc2N
• InChI: InChI=1S/C15H20N6O4/c1-4-17-13(22)9-8-10(25-15(2,3)24-8)14(23-9)21-6-20-7-11(16)18-5-19-12(7)21/h5-6,8-10,14H,4H2,1-3H3,(H,17,22)(H2,16,18,19)/t8-,9-,10?,14+/m0/s1
• InChIKey: FIHQDKWIAMIECN-BYYPQSTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,4S,6R)-6-(6-amino-9H-purin-9-yl)-N-ethyl-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxole-4-carboxamide
• IUPAC Traditional name: (3aR,4S,6R)-6-(6-aminopurin-9-yl)-N-ethyl-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide
• Synonyms: 1-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide; 2’,3’-O-isopropylidene-NECA; 5'-Ethylcarboxamido-2',3'-isopropylidene Adenosine

Database IDs

• CAS Number: 39491-53-7
• PubChem SID: 162262595
• PubChem CID: 46781533

CALCULATED PROPERTIES

• Acid pKa: 14.431794
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.40983722
• LogD (pH = 7.4): -0.29638484
• Log P: -0.2947233
• Molar Refractivity: 86.7375 cm^3
• Polarizability: 33.710064 Å^3
• Polar Surface Area: 126.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 200-202°C

DETAILS

Toronto Research Chemicals - E900995

A useful template for the development of A2B adenosine receptor agonists. It was confirmed to be a full agonist in a functional assay based on the measurement of its capacity to modulate cAMP levels in CHO cells expressing the hA2B receptor.

REFERENCES

• Kemp, B., et al.: Br. J. Pharmacol., 126, 1796 (1999)
• Peyot, M., et al.: Circ. Res., 86, 76 (1999)
• Fredholm, B., et al.: Pharmacol. Rev., 53, 527 (1999)
• Zeng, D., et al.: Drug Dev. Res., 58, 405 (1999)
• Baraldi, P., et al.: J. Med. Chem., 47, 5535 (200