7-butyl-6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazine

• ChemBase ID: 159730
• Molecular Formular: C17H19N3O
• Molecular Mass: 281.35226
• Monoisotopic Mass: 281.15281224
• SMILES: c1(c2c([nH]c1c1ccc(cc1)OC)nccn2)CCCC
• Canonical SMILES: CCCCc1c([nH]c2c1nccn2)c1ccc(cc1)OC
• InChI: InChI=1S/C17H19N3O/c1-3-4-5-14-15(12-6-8-13(21-2)9-7-12)20-17-16(14)18-10-11-19-17/h6-11H,3-5H2,1-2H3,(H,19,20)
• InChIKey: WVMANZPBOBRWCB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-butyl-6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazine
• IUPAC Traditional name: 7-butyl-6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazine
• Synonyms: RP106, 7-n-Butyl-6-(4-methoxyphenyl)-[5H]pyrrolo[2,3-b]pyrazine; Aloisine RP106

Database IDs

• CAS Number: 496864-15-4
• PubChem SID: 162253865
• PubChem CID: 3641059

CALCULATED PROPERTIES

• Acid pKa: 13.986632
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.64586
• LogD (pH = 7.4): 3.6466477
• Log P: 3.646658
• Molar Refractivity: 82.7324 cm^3
• Polarizability: 33.88857 Å^3
• Polar Surface Area: 50.8 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-white Solid
• Melting Point: 182-184°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A575475

A cell-permeable pyrrolo-pyrazine compound that acts as a potent, selective, reversible, and ATP-competitive inhibitor of Cdk1/cyclin B, Cdk5/p35, and GSK-3 ( IC50 =700nM 1.5 uM, and 920 nM, respectively).

REFERENCES

• Mattey, Y., et al.: J. Med. Chem., 46, 222 (2003)