ethyl 12-isothiocyanato-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.02,6]tetradeca-1(10),3,5,11,13-pentaene-5-carboxylate

• ChemBase ID: 165571
• Molecular Formular: C16H14N4O3S
• Molecular Mass: 342.37236
• Monoisotopic Mass: 342.07866133
• SMILES: C1(=O)N(Cc2n(c3c1cc(cc3)N=C=S)cnc2C(=O)OCC)C
• Canonical SMILES: CCOC(=O)c1ncn2c1CN(C)C(=O)c1c2ccc(c1)N=C=S
• InChI: InChI=1S/C16H14N4O3S/c1-3-23-16(22)14-13-7-19(2)15(21)11-6-10(18-9-24)4-5-12(11)20(13)8-17-14/h4-6,8H,3,7H2,1-2H3
• InChIKey: HNQZCUNPKHMCQJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 12-isothiocyanato-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,11,13-pentaene-5-carboxylate
• IUPAC Traditional name: ethyl 12-isothiocyanato-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,11,13-pentaene-5-carboxylate
• Synonyms: 5,6-Dihydro-8-isothiocyanato-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic Acid Ethyl Ester; Defluoro Flumazenil Isothiocyanate

Database IDs

• CAS Number: 954107-48-3
• PubChem SID: 162259704
• PubChem CID: 44560284

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.4345568
• LogD (pH = 7.4): 1.4369692
• Log P: 1.437
• Molar Refractivity: 104.7751 cm^3
• Polarizability: 35.184525 Å^3
• Polar Surface Area: 76.79 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D228995

An isothiocyanate derivative of Flumanezil (F500450), a benzodiazepine antagonist. Used in the study of benzodiazepine binding sites of γ-aminobutyric acid type A receptors.

REFERENCES

• Tan, K.R. et al.: J. Bio. Chem., 282, 26316 (2007)
• Hunkeler, W., et al.: Nature, 290, 514 (2007)
• Pole, P., et al.: Arch. Pharmacol., 316, 317 (2007)