N'-[(1E)-(3-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide

• ChemBase ID: 179825
• Molecular Formular: C13H11N3O2
• Molecular Mass: 241.24534
• Monoisotopic Mass: 241.08512661
• SMILES: C(=O)(N/N=C/c1cc(O)ccc1)c1ccncc1
• Canonical SMILES: Oc1cccc(c1)/C=N/NC(=O)c1ccncc1
• InChI: InChI=1S/C13H11N3O2/c17-12-3-1-2-10(8-12)9-15-16-13(18)11-4-6-14-7-5-11/h1-9,17H,(H,16,18)/b15-9+
• InChIKey: WJVBIMBJLVWPNE-OQLLNIDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N'-[(1E)-(3-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide
• IUPAC Traditional name: N'-[(1E)-(3-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide
• Synonyms: m-Oxyberon; AT-2; Acroteben

Database IDs

• CAS Number: 840-80-2
• PubChem SID: 164235735
• PubChem CID: 5351737

CALCULATED PROPERTIES

• Acid pKa: 9.105117
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.4404476
• LogD (pH = 7.4): 1.4335839
• Log P: 1.441897
• Molar Refractivity: 68.0595 cm^3
• Polarizability: 25.024733 Å^3
• Polar Surface Area: 74.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Inhibitor of mycolic acid synthesis and disruption of the cell wall in susceptible organisms

Product Information

• Description: Isomers
• Application(s): Tuberculostatic

REFERENCES

• Lourenco MC,Ferreira Mde L,de Souza MV,Peralta MA,Vasconcelos TR,Henriques MG (2008)
• Synthesis and anti-mycobacterial activity of (E)-N'-(monosubstituted-benzylidene)isonicotinohydrazide derivatives.
• European journal of medicinal chemistry 43, 1344-7