9-({[1,3-bis(benzyloxy)propan-2-yl]oxy}methyl)-6-chloro-9H-purin-2-amine

• ChemBase ID: 161740
• Molecular Formular: C23H24ClN5O3
• Molecular Mass: 453.92136
• Monoisotopic Mass: 453.15676733
• SMILES: n1c(nc2c(c1Cl)ncn2COC(COCc1ccccc1)COCc1ccccc1)N
• Canonical SMILES: Nc1nc(Cl)c2c(n1)n(COC(COCc1ccccc1)COCc1ccccc1)cn2
• InChI: InChI=1S/C23H24ClN5O3/c24-21-20-22(28-23(25)27-21)29(15-26-20)16-32-19(13-30-11-17-7-3-1-4-8-17)14-31-12-18-9-5-2-6-10-18/h1-10,15,19H,11-14,16H2,(H2,25,27,28)
• InChIKey: ZXJUDIFIAGSPQH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-({[1,3-bis(benzyloxy)propan-2-yl]oxy}methyl)-6-chloro-9H-purin-2-amine
• IUPAC Traditional name: 9-({[1,3-bis(benzyloxy)propan-2-yl]oxy}methyl)-6-chloropurin-2-amine
• Synonyms: 6-Chloro-9-[[2-(phenylmethoxy)-1-[(phenylmethoxy)methyl]ethoxy]methyl]-9H-purin-2-amine; Biolf 70; 9-[[2-Benzyloxy-1-(benzyloxymethyl)-ethoxy]-methyl]-6-chloroguanine

Database IDs

• CAS Number: 84222-47-9
• PubChem SID: 162255875
• PubChem CID: 128602

CALCULATED PROPERTIES

• Acid pKa: 16.283705
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 4.079095
• LogD (pH = 7.4): 4.079101
• Log P: 4.0791016
• Molar Refractivity: 123.83 cm^3
• Polarizability: 47.61502 Å^3
• Polar Surface Area: 97.31 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Dimethyl Sulfoxide; Ethyl Acetate; Methanol
• Apperance: Yellow Oil

DETAILS

Toronto Research Chemicals - B286050

Guanine derivative, having antimyocarditic activity.

REFERENCES

• Gauntt, C.J., et al.: Antimicrob. Ag. Chemother., 27, 184 (1985)