ethyl 1-ethyl-4-[2-(propan-2-ylidene)hydrazin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

• ChemBase ID: 105270
• Molecular Formular: C14H19N5O2
• Molecular Mass: 289.33296
• Monoisotopic Mass: 289.15387487
• SMILES: CCOC(=O)c1c(NN=C(C)C)c2c(nc1)n(CC)nc2
• Canonical SMILES: CCOC(=O)c1cnc2c(c1NN=C(C)C)cnn2CC
• InChI: InChI=1S/C14H19N5O2/c1-5-19-13-10(8-16-19)12(18-17-9(3)4)11(7-15-13)14(20)21-6-2/h7-8H,5-6H2,1-4H3,(H,15,18)
• InChIKey: OPQRBXUBWHDHPQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-ethyl-4-[2-(propan-2-ylidene)hydrazin-1-yl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
• IUPAC Traditional name: etazolate
• Synonyms: Etazolate; 1-Ethyl-4-[2-(1-methylethylidene)hydrazinyl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic Acid Ethyl Ester; 1-Ethyl-4-isopropylidenehydrazino-1H-pyrazolo[3,4-b]-1-pyridine-5-carboxylic Acid Ethyl Ester; SQ 64442; SQ 20009; ETAZOLATE HYDROCHLORIDE

Database IDs

• CAS Number: 51022-77-6
• PubChem SID: 162092075
• PubChem CID: 3277
• CHEMBL: 356388
• Chemspider ID: 3162
• Unique Ingredient Identifier: I89Y79062L
• Wikipedia Title: Etazolate

CALCULATED PROPERTIES

• Acid pKa: 13.756224
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.0902715
• LogD (pH = 7.4): 2.1590333
• Log P: 2.1847649
• Molar Refractivity: 92.4818 cm^3
• Polarizability: 30.352547 Å^3
• Polar Surface Area: 81.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 188-192°C; 92-93°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Uncontrolled

DETAILS

MP Biomedicals - 02159592

Hydrochloride
Inhibitor of phosphodiesterase IV.

Toronto Research Chemicals - E889250

An inhibitor of phosphodiesterase IV, about 8 times more active for cAMP than cGMP.

REFERENCES

• Chesin, et al.: Biochem. Pharmacol., 21, 2443 (1972)
• Ahluwalia, et al.: Biochem. Pharmacol., 31, 665 (1972)
• Nicholson, et al.: TIPS, 12, 19 (1972)