5-methyl-6-oxo-N-(1,3,4-thiadiazol-2-yl)-5H,6H,7H-furo[2,3-f]indole-7-carboxamide

• ChemBase ID: 162453
• Molecular Formular: C14H10N4O3S
• Molecular Mass: 314.3192
• Monoisotopic Mass: 314.0473612
• SMILES: c12c(cc3c(c1)occ3)N(C(=O)C2C(=O)Nc1scnn1)C
• Canonical SMILES: O=C(C1c2cc3occc3cc2N(C1=O)C)Nc1nncs1
• InChI: InChI=1S/C14H10N4O3S/c1-18-9-4-7-2-3-21-10(7)5-8(9)11(13(18)20)12(19)16-14-17-15-6-22-14/h2-6,11H,1H3,(H,16,17,19)
• InChIKey: OQMLSKSSPKAKJQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methyl-6-oxo-N-(1,3,4-thiadiazol-2-yl)-5H,6H,7H-furo[2,3-f]indole-7-carboxamide
• IUPAC Traditional name: 5-methyl-6-oxo-N-(1,3,4-thiadiazol-2-yl)-7H-furo[2,3-f]indole-7-carboxamide
• Synonyms: 6,7-Dihydro-5-methyl-6-oxo-N-1,3,4-thiadiazol-2-yl-5H-furo[2,3-f]indole-7-carboxamide; BML-288

Database IDs

• CAS Number: 851681-89-5
• PubChem SID: 162256588
• PubChem CID: 11438405

CALCULATED PROPERTIES

• Acid pKa: 3.7778986
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.99253
• LogD (pH = 7.4): -2.3366363
• Log P: 0.7235165
• Molar Refractivity: 80.9154 cm^3
• Polarizability: 30.323448 Å^3
• Polar Surface Area: 88.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B595880

A potent and selective inhibitor of phosphodiesterase Type II (PDE2). It demonstrated no inhibition of 5-lipoxygenase (5-LO) or cyclooxygenase (COX-1) and is more potent and selective than EHNA (H825550).

REFERENCES

• Chambers, R.J. et al.: Bioorg. Med. Chem. Lett., 16, 307 (2006)