N-{4-[(4aS,10bR)-8,9-dimethoxy-2-methyl-1H,2H,3H,4H,4aH,10bH-benzo[c]1,6-naphthyridin-6-yl]phenyl}-4-methylbenzene-1-sulfonamide

• ChemBase ID: 178696
• Molecular Formular: C28H31N3O4S
• Molecular Mass: 505.62844
• Monoisotopic Mass: 505.20352749
• SMILES: [C@@H]12[C@@H](N=C(c3c1cc(c(c3)OC)OC)c1ccc(cc1)NS(=O)(=O)c1ccc(cc1)C)CCN(C2)C
• Canonical SMILES: COc1cc2[C@@H]3CN(C)CC[C@@H]3N=C(c2cc1OC)c1ccc(cc1)NS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C28H31N3O4S/c1-18-5-11-21(12-6-18)36(32,33)30-20-9-7-19(8-10-20)28-23-16-27(35-4)26(34-3)15-22(23)24-17-31(2)14-13-25(24)29-28/h5-12,15-16,24-25,30H,13-14,17H2,1-4H3/t24-,25-/m0/s1
• InChIKey: FVZJIAUYFDQQKJ-DQEYMECFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(4aS,10bR)-8,9-dimethoxy-2-methyl-1H,2H,3H,4H,4aH,10bH-benzo[c]1,6-naphthyridin-6-yl]phenyl}-4-methylbenzene-1-sulfonamide
• IUPAC Traditional name: N-{4-[(4aS,10bR)-8,9-dimethoxy-2-methyl-1H,3H,4H,4aH,10bH-benzo[c]1,6-naphthyridin-6-yl]phenyl}-4-methylbenzenesulfonamide
• Synonyms: rel-(-)-N-[4-[(4aR,10bS)-1,2,3,4,4a,10b-Hexahydro-8,9-dimethoxy-2-methylbenzo[c][1,6]naphthyridin-6-yl]phenyl]-4-methylbenzenesulfonamide; Tolafentrine

Database IDs

• CAS Number: 139308-65-9
• PubChem SID: 164234606
• PubChem CID: 65990

CALCULATED PROPERTIES

• Acid pKa: 7.796791
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.2778642
• LogD (pH = 7.4): 2.9690824
• Log P: 3.2677453
• Molar Refractivity: 142.2916 cm^3
• Polarizability: 55.16187 Å^3
• Polar Surface Area: 80.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T531000

A dual-selective phosphodiesterase 3/4 inhibitor used in chronic experimental pulmonary hypertension.

REFERENCES

• Huxtable, R., et al.: Pharmacol. Ther., 47, 371 (1990)
• Tanaka, K., et al.: Cancer Res., 55, 2927 (1990)
• Wagner, R., et al.: J. Pharmacol. Exp. Ther., 282, 1650 (1990)
• Cowan, K., et al.: Nat. Med., 6, 698 (1990)
• Shankavaram, U., et al.: J. Biol. Chem.,