5-bromo-N-(2,3-dihydroxypropoxy)-3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzamide

• ChemBase ID: 72748
• Molecular Formular: C16H13BrF3IN2O4
• Molecular Mass: 561.0890996
• Monoisotopic Mass: 559.90555157
• SMILES: c1c(c(c(c(c1C(=O)NOCC(CO)O)Nc1ccc(cc1F)I)F)F)Br
• Canonical SMILES: OCC(CONC(=O)c1cc(Br)c(c(c1Nc1ccc(cc1F)I)F)F)O
• InChI: InChI=1S/C16H13BrF3IN2O4/c17-10-4-9(16(26)23-27-6-8(25)5-24)15(14(20)13(10)19)22-12-2-1-7(21)3-11(12)18/h1-4,8,22,24-25H,5-6H2,(H,23,26)
• InChIKey: XXSSGBYXSKOLAM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromo-N-(2,3-dihydroxypropoxy)-3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzamide
• IUPAC Traditional name: C16H13BrF3IN2O4
• Synonyms: PD318088

Database IDs

• CAS Number: 391210-00-7
• PubChem SID: 162037669
• PubChem CID: 10231331

CALCULATED PROPERTIES

• Acid pKa: 11.605959
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 4.7439566
• LogD (pH = 7.4): 4.7439327
• Log P: 4.743957
• Molar Refractivity: 103.7588 cm^3
• Polarizability: 39.281628 Å^3
• Polar Surface Area: 90.82 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: MEK

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1568

Research Area

• Description: Cancer

Biological Activity

• Description: PD318088 is a non-ATP competitive allosteric MEK1/2 inhibitor.
• Targets: MEK1/2
• In Vitro: PD318088 is a small-molecule inhibitor of MEK1/2, which is an analog of PD184352, suggesting it might have substantial anti-proliferative activity against cancer cells, although no functional study of PD318088 is currently available. PD318088 binds simultaneously with ATP in a region of the MEK1 active site that is adjacent to the ATP-binding site. Formation of the ternary complexes with PD318088 and MgATP results in moderate increases (to 140 nM) for the K_d monomer-dimer for both MEK1 and MEK2. The binding of PD318088 and MgATP to MEK1 also abolishes the formation of tetramers and higher-order aggregates. PD318088 and MgATP together increase the dimerization disassociation constant for MEK1 and MEK2 slightly from ~75 nM to ~140 nM, suggesting that the mechanism of inhibition for PD318088 is probably a result of localized conformational changes in the active site and not a global change in the overall structure. ^[1]

References

• References: [1] Ohren JF, et al. Nat Struct Mol Biol, 2004, 11(12), 1192-1197.

REFERENCES

• Ohren JF, et al. Nat Struct Mol Biol, 2004, 11(12), 1192-1197.