7-methyl-1,5-dioxo-1,2,3,5-tetrahydroindolizine-6-carbonitrile

• ChemBase ID: 178384
• Molecular Formular: C10H8N2O2
• Molecular Mass: 188.18272
• Monoisotopic Mass: 188.05857751
• SMILES: c1(c(c(=O)n2c(c1)C(=O)CC2)C#N)C
• Canonical SMILES: N#Cc1c(C)cc2n(c1=O)CCC2=O
• InChI: InChI=1S/C10H8N2O2/c1-6-4-8-9(13)2-3-12(8)10(14)7(6)5-11/h4H,2-3H2,1H3
• InChIKey: WAVYZKPFLMIKCX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-methyl-1,5-dioxo-1,2,3,5-tetrahydroindolizine-6-carbonitrile
• IUPAC Traditional name: 7-methyl-1,5-dioxo-2,3-dihydroindolizine-6-carbonitrile
• Synonyms: 1,2,3,5-Tetrahydro-7-methyl-1,5-dioxo-6-indolizinecarbonitrile

Database IDs

• CAS Number: 58610-63-2
• PubChem SID: 164234294
• PubChem CID: 10921274

CALCULATED PROPERTIES

• Acid pKa: 18.910105
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.19135164
• LogD (pH = 7.4): 0.19135164
• Log P: 0.19135164
• Molar Refractivity: 51.2743 cm^3
• Polarizability: 18.375654 Å^3
• Polar Surface Area: 61.17 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: Light Brown Solid

DETAILS

Toronto Research Chemicals - T293950

Intermediate in the preparation of Camptothecin derivatives, for their therapeutic use as antitumor agents.

REFERENCES

• Wani, M.C., et al.: J. Med. Chem., 29, 2358 (1986)
• Miller, K.D., et al.: Invest. New Drugs, 22, 69 (1986)
• Punt, C.J.A., et al.: Eur. J. Cancer, 40, 1332 (1986)
• Wang, J.-Q., et al.: Bioorg. Med. Chem., 13, 549 (2005)