N'-[(1E)-(2-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide

• ChemBase ID: 179797
• Molecular Formular: C13H11N3O2
• Molecular Mass: 241.24534
• Monoisotopic Mass: 241.08512661
• SMILES: C(=O)(N/N=C/c1c(O)cccc1)c1ccncc1
• Canonical SMILES: O=C(c1ccncc1)N/N=C/c1ccccc1O
• InChI: InChI=1S/C13H11N3O2/c17-12-4-2-1-3-11(12)9-15-16-13(18)10-5-7-14-8-6-10/h1-9,17H,(H,16,18)/b15-9+
• InChIKey: VBIZUNYMJSPHBH-OQLLNIDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N'-[(1E)-(2-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide
• IUPAC Traditional name: N'-[(1E)-(2-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide
• Synonyms: Salicylaldehyde isonicotinoylhydrazone; Acozid; Nicozid; Nilazid; Nupasal; Phthiosan; Saliniazid; Salizid; Salinazid

Database IDs

• CAS Number: 495-84-1
• PubChem SID: 164235707
• PubChem CID: 5359410

CALCULATED PROPERTIES

• Acid pKa: 8.725953
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.440309
• LogD (pH = 7.4): 1.4220748
• Log P: 1.441897
• Molar Refractivity: 68.0595 cm^3
• Polarizability: 25.02636 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; Interferes with several bacterial Enzyme systems

Product Information

• Application(s): Antiseptic; Used in treatment of tuberculosis

REFERENCES

• Yale, H. et al., J.A.C.S., 1953, 75, 1933, (synth)
• Hart, J.J.D. et al., Antibiot. Chemother. (Washington, D.C.), 1954, 4, 803, (synth, props)
• Bavin, E.M. et al., J. Pharm. Pharmacol., 1955, 7, 1032, (pharmacol, tox)
• Chakvaranty, D. et al., J. Pharm. Sci., 1964, 53, 1036, (synth, use)
• Cowper, A.J. et al., J. Inst. Chem. (India), 1981, 53, 111; 195, (synth, pharmacol)
• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 7570