8-[(4-iodo-2H-1,3-benzodioxol-5-yl)sulfanyl]-9-{3-[(propan-2-yl)amino]propyl}-9H-purin-6-amine

• ChemBase ID: 177108
• Molecular Formular: C18H21IN6O2S
• Molecular Mass: 512.36781
• Monoisotopic Mass: 512.04914294
• SMILES: c1nc(c2c(n1)n(c(n2)Sc1ccc2c(c1I)OCO2)CCCNC(C)C)N
• Canonical SMILES: CC(NCCCn1c(Sc2ccc3c(c2I)OCO3)nc2c1ncnc2N)C
• InChI: InChI=1S/C18H21IN6O2S/c1-10(2)21-6-3-7-25-17-14(16(20)22-8-23-17)24-18(25)28-12-5-4-11-15(13(12)19)27-9-26-11/h4-5,8,10,21H,3,6-7,9H2,1-2H3,(H2,20,22,23)
• InChIKey: ISNXXKIVVRMYNP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[(4-iodo-2H-1,3-benzodioxol-5-yl)sulfanyl]-9-{3-[(propan-2-yl)amino]propyl}-9H-purin-6-amine
• IUPAC Traditional name: 8-[(4-iodo-2H-1,3-benzodioxol-5-yl)sulfanyl]-9-[3-(isopropylamino)propyl]purin-6-amine
• Synonyms: 6-Amino-8-[(6-iodo-1,3-benzodioxol-5-yl)thio]-N-(1-methylethyl)-9H-purine-9-propanamine Hydrate; PU-H71 Hydrate

Database IDs

• CAS Number: 1202865-65-3
• PubChem SID: 164233018
• PubChem CID: 71751876

CALCULATED PROPERTIES

• Acid pKa: 18.395834
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.24802205
• LogD (pH = 7.4): 0.6952138
• Log P: 3.58678
• Molar Refractivity: 119.54 cm^3
• Polarizability: 46.08666 Å^3
• Polar Surface Area: 100.11 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P840120

PU-H71 is a potent Hsp90 inhibitor (IC50 = 50 nM). Hsp90 plays a critical role in modulating the activity of many cell signaling proteins and are an attractive target for anti-cancer therapeutics. Studies indicate that Hsp90 inhibitors may serve as potent

REFERENCES

• Gewirth, D.T., et al.: J. Med. Chem., 49, 381 (2006)
• Taldone, T., et al.: Bioorh. Med. Chem., 17, 2225 (2006)