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

• ChemBase ID: 179781
• Molecular Formular: C14H13N3O3
• Molecular Mass: 271.27132
• Monoisotopic Mass: 271.09569129
• SMILES: C(=O)(N/N=C/c1cc(c(cc1)O)OC)c1ccncc1
• Canonical SMILES: COc1cc(/C=N/NC(=O)c2ccncc2)ccc1O
• InChI: InChI=1S/C14H13N3O3/c1-20-13-8-10(2-3-12(13)18)9-16-17-14(19)11-4-6-15-7-5-11/h2-9,18H,1H3,(H,17,19)/b16-9+
• InChIKey: PSWOBQSIXLVPDV-CXUHLZMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N'-[(1E)-(4-hydroxy-3-methoxyphenyl)methylidene]pyridine-4-carbohydrazide
• IUPAC Traditional name: N'-[(1E)-(4-hydroxy-3-methoxyphenyl)methylidene]pyridine-4-carbohydrazide
• Synonyms: Phthivazid; Isovin; Vanizide; Vanillaberon; Ftivazide

Database IDs

• CAS Number: 149-17-7
• PubChem SID: 164235691
• PubChem CID: 5479610

CALCULATED PROPERTIES

• Acid pKa: 9.40966
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.2828305
• LogD (pH = 7.4): 1.2801563
• Log P: 1.2842257
• Molar Refractivity: 74.5227 cm^3
• Polarizability: 27.561325 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; Interferes with several bacterial Enzyme systems

Product Information

• Application(s): Antiseptic; Tuberculostatic agent

REFERENCES

• Sodikov, E.S. et al., Farmakol. Toksikol. (Moscow), 1968, 31, 348, (pharmacol, tox)
• Grebennik, L.I., Sov. Med., 1968, 31, 47, (metab)
• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 7565
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VEZ925