(2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxo-1,2-dihydropyridin-1-yl]-N-hydroxy-2-methanesulfonyl-2-methylbutanamide

• ChemBase ID: 176423
• Molecular Formular: C18H21FN2O6S
• Molecular Mass: 412.4325432
• Monoisotopic Mass: 412.11043562
• SMILES: c1c(cc(c(c1)c1cc(=O)n(cc1)CC[C@](C(=O)NO)(S(=O)(=O)C)C)F)OC
• Canonical SMILES: ONC(=O)[C@](S(=O)(=O)C)(CCn1ccc(cc1=O)c1ccc(cc1F)OC)C
• InChI: InChI=1S/C18H21FN2O6S/c1-18(17(23)20-24,28(3,25)26)7-9-21-8-6-12(10-16(21)22)14-5-4-13(27-2)11-15(14)19/h4-6,8,10-11,24H,7,9H2,1-3H3,(H,20,23)/t18-/m1/s1
• InChIKey: DNVUWHWBCMGQLU-GOSISDBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxo-1,2-dihydropyridin-1-yl]-N-hydroxy-2-methanesulfonyl-2-methylbutanamide
• IUPAC Traditional name: (2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1-yl]-N-hydroxy-2-methanesulfonyl-2-methylbutanamide
• Synonyms: (αR)-4-(2-Fluoro-4-methoxyphenyl)-N-hydroxy-α-methyl-α-(methylsulfonyl)-2-oxo-1(2H)-pyridinebutanamide; PF-5081090

Database IDs

• CAS Number: 1312473-63-4
• PubChem SID: 164232333
• PubChem CID: 56964907

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 8.667716
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.0977854
• LogD (pH = 7.4): 0.075356
• Log P: 0.09807906
• Molar Refractivity: 101.309 cm^3
• Polarizability: 39.009865 Å^3
• Polar Surface Area: 113.01 Å^2
• Rotatable Bonds: 7

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Beige Solid
• Melting Point: 178-180°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P294040

PF-5081090 is a pyridone methylsulfone hydroxamate LpxC inhibitor. PF-5081090 is used as an antibiotic in the treatment of serious gram-negative infections.

REFERENCES

• J. Med. Chem., 2012, 55, 1662-1670