4-amino-5-fluoro-3-{6-[(2,2,3,3,5,5,6,6-2H8)piperazin-1-yl]-1H-1,3-benzodiazol-2-yl}-1,2-dihydroquinolin-2-one

• ChemBase ID: 166437
• Molecular Formular: C20H19FN6O
• Molecular Mass: 378.4028632
• Monoisotopic Mass: 378.16043748
• SMILES: c1cc(c2c(c1)[nH]c(=O)c(c2N)c1nc2c([nH]1)cc(cc2)N1CCNCC1)F
• Canonical SMILES: O=c1[nH]c2cccc(c2c(c1c1nc2c([nH]1)cc(cc2)N1CCNCC1)N)F
• InChI: InChI=1S/C20H19FN6O/c21-12-2-1-3-14-16(12)18(22)17(20(28)26-14)19-24-13-5-4-11(10-15(13)25-19)27-8-6-23-7-9-27/h1-5,10,23H,6-9H2,(H,24,25)(H3,22,26,28)
• InChIKey: DRUNJGIEUWMQHG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-3-{6-[(2,2,3,3,5,5,6,6-^2H₈)piperazin-1-yl]-1H-1,3-benzodiazol-2-yl}-1,2-dihydroquinolin-2-one
• IUPAC Traditional name: 4-amino-5-fluoro-3-{5-[(2,2,3,3,5,5,6,6-^2H₈)piperazin-1-yl]-3H-1,3-benzodiazol-2-yl}-1H-quinolin-2-one
• Synonyms: 4-Amino-5-fluoro-3-[6-(1-piperazinyl-d8)-1H-benzimidazol-2-yl]-2(1H)-quinolinone; N-Desmethyl Dovitinib-d8

Database IDs

• PubChem SID: 162260570
• PubChem CID: 71315736

CALCULATED PROPERTIES

• Acid pKa: 8.856774
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.7444378
• LogD (pH = 7.4): -0.21244271
• Log P: 0.72720283
• Molar Refractivity: 107.0692 cm^3
• Polarizability: 40.216583 Å^3
• Polar Surface Area: 99.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D291627

Labelled Dovitinib (D537000 )derivative; a benzimidazole quinolinone for inhibiting a checkpoint kinase 1 and its use in combination therapy for cancer.

REFERENCES

• Bosserhoff, A., et al.: J. Investigative Dermat., 114, 395 (2000)
• Anon., et al.: Eur. J. Cancer, 3 (suppl. 2), 148 (2000)