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

• ChemBase ID: 161246
• Molecular Formular: C20H18N2O4
• Molecular Mass: 350.36792
• Monoisotopic Mass: 350.12665707
• SMILES: c1ccc2c(c1)c1c([nH]2)[C@H](N[C@H](C1)C(=O)OC)c1cc2c(cc1)OCO2
• Canonical SMILES: COC(=O)[C@@H]1N[C@H](c2ccc3c(c2)OCO3)c2c(C1)c1ccccc1[nH]2
• InChI: InChI=1S/C20H18N2O4/c1-24-20(23)15-9-13-12-4-2-3-5-14(12)21-19(13)18(22-15)11-6-7-16-17(8-11)26-10-25-16/h2-8,15,18,21-22H,9-10H2,1H3/t15-,18-/m1/s1
• InChIKey: LIPVUDSNGRJSQE-CRAIPNDOSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 171596-44-4; 171596-41-1
• PubChem SID: 162255381
• PubChem CID: 10269318

CALCULATED PROPERTIES

• Acid pKa: 15.185053
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.803077
• LogD (pH = 7.4): 2.8331563
• Log P: 2.8335536
• Molar Refractivity: 94.2283 cm^3
• Polarizability: 38.345318 Å^3
• Polar Surface Area: 72.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Dimethylformamide; Ethyl Acetate
• Apperance: Light Yellow Powder; White Solid
• Melting Point: 83-85°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B200025

Tadalafil (T004500) derivative. Used in the preparation of pyrazinopyridoindole derivatives for their PDE5 inhibitory activity.

Toronto Research Chemicals - M330150

An intermediate and impurity in the synthesis of Tadafil.

REFERENCES

• Beghyn, T. et al.: Bioorgan. Med. Chem. Lett. 17, 789(2007)
• Carrier, S., et al.: Can. J. Urol., 10(1)
• 12 (1)