6H,12H-indolo[2,1-b]quinazoline-6,12-dione

• ChemBase ID: 179755
• Molecular Formular: C15H8N2O2
• Molecular Mass: 248.23622
• Monoisotopic Mass: 248.05857751
• SMILES: n12c(nc3c(c1=O)cccc3)C(=O)c1c2cccc1
• Canonical SMILES: O=C1c2nc3ccccc3c(=O)n2c2c1cccc2
• InChI: InChI=1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H
• InChIKey: VQQVWGVXDIPORV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6H,12H-indolo[2,1-b]quinazoline-6,12-dione
• IUPAC Traditional name: 6H,12H-indolo[2,1-b]quinazoline-6,12-dione
• Synonyms: Couroupitine A; Tryptanthrine

Database IDs

• CAS Number: 13220-57-0
• PubChem SID: 164235665
• PubChem CID: 73549

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.3956623
• LogD (pH = 7.4): 2.3956623
• Log P: 2.3956623
• Molar Refractivity: 71.6182 cm^3
• Polarizability: 25.91189 Å^3
• Polar Surface Area: 49.74 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: AhR-Agonist

Product Information

• Biological Source: Isol. from the yeast Candida lipolytica grown in the presence of L-Trytophan. Also from Couroupita guianensis (Lecythidaceae), Isatis indigotica and Polygonum tiucforum
• Application(s): Active against Helicobacter pylori; Antifungal and antimicrobial agent showing specific activity against dermatophytes

REFERENCES

• Brufani, M. et al., Experientia, 1971, 27, 1249, (cryst struct, pmr, ms)
• Fedeli, W. et al., J.C.S. Perkin 2, 1974, 1621, (cryst struct)
• Bergman, J. et al., Tet. Lett., 1977, 2625, (struct, synth)
• Karpf, H. et al., Tet. Lett., 1978, 3007, (synth, ir, uv, ms)
• Honda, G. et al., Planta Med., 1979, 37, 172, (props)
• Mitscher, L.A. et al., Heterocycles, 1981, 15, 1017, (synth)
• Capuano, L. et al., Chem. Ber., 1983, 116, 741, (synth)
• Eguchi, S. et al., Heterocycles, 1992, 33, 153, (synth)
• Cornforth, J. et al., J.C.S. Perkin 1, 1996, 2787, (synth)
• Hashimoto, T. et al., Nat. Med. (N.Y.), 1999, 53, 27, (isol, activity)