5-methoxy-2,3,4,9-tetrahydro-1H-carbazole

• ChemBase ID: 178380
• Molecular Formular: C13H15NO
• Molecular Mass: 201.2643
• Monoisotopic Mass: 201.11536411
• SMILES: c1ccc2c(c1OC)c1c([nH]2)CCCC1
• Canonical SMILES: COc1cccc2c1c1CCCCc1[nH]2
• InChI: InChI=1S/C13H15NO/c1-15-12-8-4-7-11-13(12)9-5-2-3-6-10(9)14-11/h4,7-8,14H,2-3,5-6H2,1H3
• InChIKey: HAJZMJYKAQQJIS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methoxy-2,3,4,9-tetrahydro-1H-carbazole
• IUPAC Traditional name: 4-methoxy-6,7,8,9-tetrahydro-5H-carbazole
• Synonyms: 2,3,4,9-Tetrahydro-5-methoxy-1H-carbazole; 1,2,3,4-Tetrahydro-5-methoxycarbazole

Database IDs

• CAS Number: 68962-14-1
• PubChem SID: 164234290
• PubChem CID: 12717079

CALCULATED PROPERTIES

• Acid pKa: 17.514374
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.1306844
• LogD (pH = 7.4): 3.1306844
• Log P: 3.1306844
• Molar Refractivity: 61.1214 cm^3
• Polarizability: 24.579643 Å^3
• Polar Surface Area: 25.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T293890

Used in the synthesis of C-15 Vindoline analogues. A carbazole derivative as potassium channel blocker for ophthalmic compositions for treating ocular hypertension.

REFERENCES

• Barnett, C., et al.: J. Med. Chem., 21, 88 (1978)
• Gregory, R., et al.: Br. J. Cancer, 82, 1907 (1978)
• Fahy, J., et al.: Bioorg. Med. Chem. Lett., 12, 505 (1978)