methyl (1S,3R)-1-(2H-1,3-benzodioxol-5-yl)-3-(2-chloroacetyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-2-carboxylate

• ChemBase ID: 161140
• Molecular Formular: C22H19ClN2O5
• Molecular Mass: 426.84966
• Monoisotopic Mass: 426.0982494
• SMILES: c12c([C@@H](N([C@H](C1)C(=O)CCl)C(=O)OC)c1ccc3c(c1)OCO3)[nH]c1c2cccc1
• Canonical SMILES: COC(=O)N1[C@H](Cc2c([C@@H]1c1ccc3c(c1)OCO3)[nH]c1c2cccc1)C(=O)CCl
• InChI: InChI=1S/C22H19ClN2O5/c1-28-22(27)25-16(17(26)10-23)9-14-13-4-2-3-5-15(13)24-20(14)21(25)12-6-7-18-19(8-12)30-11-29-18/h2-8,16,21,24H,9-11H2,1H3/t16-,21+/m1/s1
• InChIKey: VDWINSZXOWCUBP-IERDGZPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,3R)-1-(2H-1,3-benzodioxol-5-yl)-3-(2-chloroacetyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-2-carboxylate
• IUPAC Traditional name: methyl (1S,3R)-1-(2H-1,3-benzodioxol-5-yl)-3-(2-chloroacetyl)-1H,3H,4H,9H-pyrido[3,4-b]indole-2-carboxylate
• Synonyms: (1S,3R)-1-(1,3-Benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester; (1S,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester; (1S,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloro-acetyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid Methyl Ester

Database IDs

• CAS Number: 629652-40-0
• PubChem SID: 162255275
• PubChem CID: 71313634

CALCULATED PROPERTIES

• Acid pKa: 15.085315
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.7838624
• LogD (pH = 7.4): 3.7838624
• Log P: 3.7838624
• Molar Refractivity: 108.953 cm^3
• Polarizability: 43.557426 Å^3
• Polar Surface Area: 80.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B121700

An intermediate in the preparation of cis-Tadalafil (T004520). A PDE5 inhibitor.

REFERENCES

• Beghyn, T. et al.: Bioorg. Med. Chem. Lett., 17, 789 (2007)
• Daugan, A. et al.: J. Med. Chem., 46, 4533 (2007)