4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide

• ChemBase ID: 166403
• Molecular Formular: C26H27N5O6S
• Molecular Mass: 537.58748
• Monoisotopic Mass: 537.16820461
• SMILES: c1cc(ccc1S(=O)(=O)Nc1nc(nc(c1Oc1ccccc1O)OCCO)c1ncccn1)C(C)(C)C
• Canonical SMILES: OCCOc1nc(nc(c1Oc1ccccc1O)NS(=O)(=O)c1ccc(cc1)C(C)(C)C)c1ncccn1
• InChI: InChI=1S/C26H27N5O6S/c1-26(2,3)17-9-11-18(12-10-17)38(34,35)31-22-21(37-20-8-5-4-7-19(20)33)25(36-16-15-32)30-24(29-22)23-27-13-6-14-28-23/h4-14,32-33H,15-16H2,1-3H3,(H,29,30,31)
• InChIKey: STTLKJGYAWXIPP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide
• IUPAC Traditional name: 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzenesulfonamide
• Synonyms: 4-(1,1-Dimethylethyl)-N-[6-(2-hydroxyethoxy)-5-(2-hydroxyphenoxy)[2,2’-bipyrimidin]-4-yl]benzenesulfonamide; Ro 47-8634; Desmethyl Bosentan

Database IDs

• CAS Number: 253688-61-8
• PubChem SID: 162260536
• PubChem CID: 6426756

CALCULATED PROPERTIES

• Acid pKa: 5.794843
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 4.698546
• LogD (pH = 7.4): 3.8495073
• Log P: 4.858381
• Molar Refractivity: 162.1749 cm^3
• Polarizability: 54.498894 Å^3
• Polar Surface Area: 156.65 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol; Sparingly Soluble in Chloroform
• Apperance: Green-Yellowish Solid
• Melting Point: 128-130°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291275

A metabolite of Bosentan, a mixed endothelin receptor antagonist which is used as a vasodilator.

REFERENCES

• Clozel, M., et al.: J. Pharmacol. Exp. Ther., 270, 228 (1994)
• Gutsch, G., et al.: Cardiovasc. Drugs Ther., 10, 717 (1994)
• Weber, C., et al.: Clin Pharmacol. Ther., 60, 124 (1994)
• Krum, H., et al.: N. Engl. J. Med., 338, 784 (1998)