N'-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-4-carbohydrazide

• ChemBase ID: 179822
• Molecular Formular: C14H13N3O3
• Molecular Mass: 271.27132
• Monoisotopic Mass: 271.09569129
• SMILES: C(=O)(N/N=C/c1c(c(OC)ccc1)O)c1ccncc1
• Canonical SMILES: COc1cccc(c1O)/C=N/NC(=O)c1ccncc1
• InChI: InChI=1S/C14H13N3O3/c1-20-12-4-2-3-11(13(12)18)9-16-17-14(19)10-5-7-15-8-6-10/h2-9,18H,1H3,(H,17,19)/b16-9+
• InChIKey: VWLOTRPSIVIFDW-CXUHLZMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N'-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-4-carbohydrazide
• IUPAC Traditional name: N'-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-4-carbohydrazide
• Synonyms: INH-o-van; Vanillin isoniazid

Database IDs

• CAS Number: 7209-85-0
• PubChem SID: 164235732
• PubChem CID: 5493999

CALCULATED PROPERTIES

• Acid pKa: 9.17405
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.2828057
• LogD (pH = 7.4): 1.2771513
• Log P: 1.2842257
• Molar Refractivity: 74.5227 cm^3
• Polarizability: 27.56362 Å^3
• Polar Surface Area: 83.81 Å^2
• Rotatable Bonds: 4
• 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; Iron chelator

Product Information

• Application(s): Antimalarial; Antiseptic; Tuberculostatic

REFERENCES

• Melnyk P,Leroux V,Sergheraert C,Grellier P (2006)
• Design, synthesis and in vitro antimalarial activity of an acylhydrazone library.
• Bioorganic & medicinal chemistry letters 16, 31-5