N-[(3,4-dimethoxyphenyl)methyl]-2-{[(2S)-1-hydroxypropan-2-yl]amino}-5-nitrobenzamide

• ChemBase ID: 179594
• Molecular Formular: C19H23N3O6
• Molecular Mass: 389.40242
• Monoisotopic Mass: 389.15868547
• SMILES: c1(cc(c(cc1)OC)OC)CNC(=O)c1c(ccc(c1)[N+](=O)[O-])N[C@H](CO)C
• Canonical SMILES: OC[C@@H](Nc1ccc(cc1C(=O)NCc1ccc(c(c1)OC)OC)[N+](=O)[O-])C
• InChI: InChI=1S/C19H23N3O6/c1-12(11-23)21-16-6-5-14(22(25)26)9-15(16)19(24)20-10-13-4-7-17(27-2)18(8-13)28-3/h4-9,12,21,23H,10-11H2,1-3H3,(H,20,24)/t12-/m0/s1
• InChIKey: ZISFCTXLAXIEMV-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3,4-dimethoxyphenyl)methyl]-2-{[(2S)-1-hydroxypropan-2-yl]amino}-5-nitrobenzamide
• IUPAC Traditional name: N-[(3,4-dimethoxyphenyl)methyl]-2-{[(2S)-1-hydroxypropan-2-yl]amino}-5-nitrobenzamide
• Synonyms: N-[(3,4-Dimethoxyphenyl)methyl]-2-[[(1S)-2-hydroxy-1-methylethyl]amino]-5-nitro-benzamide; (S)-Xanthoanthrafil

Database IDs

• CAS Number: 247567-47-1
• PubChem SID: 164235504
• PubChem CID: 29919043

CALCULATED PROPERTIES

• Polarizability: 38.852085 Å^3
• Polar Surface Area: 125.64 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• Acid pKa: 14.109567
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.245928
• LogD (pH = 7.4): 2.245928
• Log P: 2.245928
• Molar Refractivity: 105.8017 cm^3

DETAILS

Toronto Research Chemicals - X500010

Intermediate in the preparation of cGMP-phosphodiesterase inhibitors.

REFERENCES

• Luddens, H., et al.: Eur. J. Pharmacol., 344, 269 (1998)