2-({4-chloro-6-[(4-phenylphenyl)amino]pyrimidin-2-yl}sulfanyl)octanoic acid

• ChemBase ID: 171484
• Molecular Formular: C24H26ClN3O2S
• Molecular Mass: 456.00014
• Monoisotopic Mass: 455.14342577
• SMILES: C(CCCCC(Sc1nc(cc(n1)Nc1ccc(cc1)c1ccccc1)Cl)C(=O)O)C
• Canonical SMILES: CCCCCCC(C(=O)O)Sc1nc(Nc2ccc(cc2)c2ccccc2)cc(n1)Cl
• InChI: InChI=1S/C24H26ClN3O2S/c1-2-3-4-8-11-20(23(29)30)31-24-27-21(25)16-22(28-24)26-19-14-12-18(13-15-19)17-9-6-5-7-10-17/h5-7,9-10,12-16,20H,2-4,8,11H2,1H3,(H,29,30)(H,26,27,28)
• InChIKey: MLNIGXYHGQLWLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({4-chloro-6-[(4-phenylphenyl)amino]pyrimidin-2-yl}sulfanyl)octanoic acid
• IUPAC Traditional name: 2-({4-chloro-6-[(4-phenylphenyl)amino]pyrimidin-2-yl}sulfanyl)octanoic acid
• Synonyms: 2-[[4-([1,1'-biphenyl]-4-ylamino)-6-chloro-2-pyrimidinyl]thio]octanoic Acid; HZ 52; HZ-52

Database IDs

• PubChem SID: 164227394
• PubChem CID: 25179909

CALCULATED PROPERTIES

• Acid pKa: 3.7073271
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 6.086813
• LogD (pH = 7.4): 4.5879965
• Log P: 7.7633696
• Molar Refractivity: 128.8833 cm^3
• Polarizability: 50.46454 Å^3
• Polar Surface Area: 75.11 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H999750

A potent, reversible inhibitor of 5-lipoxygenase, blocking leukotriene synthesis with an IC50 value of 0.7 μM in intact human polymorphonuclear leukocytes. It also attenuates leukotriene B4 synthesis, prevents carrageenan-induced pleurisy, and protects ag

REFERENCES

• Greiner, C. et al.: Br. J. Pharmacol., 164, 781 (2011)
• Koeberle, A. et al.: J. Med. Chem., 51, 8068 (2011)