4-{[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}-3,3-dimethylbutanoic acid

• ChemBase ID: 174792
• Molecular Formular: C35H38ClNO3S
• Molecular Mass: 588.19912
• Monoisotopic Mass: 587.22609276
• SMILES: c1cc(cc2c1ccc(n2)/C=C/c1cccc(c1)[C@@H](CCc1c(cccc1)C(O)(C)C)SCC(CC(=O)O)(C)C)Cl
• Canonical SMILES: OC(=O)CC(CS[C@@H](c1cccc(c1)/C=C/c1ccc2c(n1)cc(cc2)Cl)CCc1ccccc1C(O)(C)C)(C)C
• InChI: InChI=1S/C35H38ClNO3S/c1-34(2,22-33(38)39)23-41-32(19-15-25-9-5-6-11-30(25)35(3,4)40)27-10-7-8-24(20-27)12-17-29-18-14-26-13-16-28(36)21-31(26)37-29/h5-14,16-18,20-21,32,40H,15,19,22-23H2,1-4H3,(H,38,39)/b17-12+/t32-/m1/s1
• InChIKey: AQCSHUUQIJHHLI-FQUAKNSKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}-3,3-dimethylbutanoic acid
• IUPAC Traditional name: 4-{[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}-3,3-dimethylbutanoic acid
• Synonyms: [R-(E)]-3-[[[1-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-3-methylbutanoic Acid; Montelukast Gem-dimethylmethylene Analogue

Database IDs

• CAS Number: 162489-70-5
• PubChem SID: 164230702
• PubChem CID: 10099896

CALCULATED PROPERTIES

• Acid pKa: 4.5009036
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 8.106791
• LogD (pH = 7.4): 6.3417115
• Log P: 8.985934
• Molar Refractivity: 171.3061 cm^3
• Polarizability: 67.82925 Å^3
• Polar Surface Area: 70.42 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M568025

An analog of Montelukast, used for preparation of MK-0476, a potent and orally active leukotriene D4 receptor antagonist devoid of peroxisomal enzyme induction.

REFERENCES

• Labelle, M., et al.: Bioorg. Med. Chem. Lett., 5, 283 (1995)