2-amino-N'-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-1,3-thiazole-5-carbohydrazide

• ChemBase ID: 154520
• Molecular Formular: C13H14N4O3S
• Molecular Mass: 306.34026
• Monoisotopic Mass: 306.07866133
• SMILES: Cc1c(sc(n1)N)C(=O)N/N=C/c1ccc(c(c1)OC)O
• Canonical SMILES: COc1cc(/C=N/NC(=O)c2sc(nc2C)N)ccc1O
• InChI: InChI=1S/C13H14N4O3S/c1-7-11(21-13(14)16-7)12(19)17-15-6-8-3-4-9(18)10(5-8)20-2/h3-6,18H,1-2H3,(H2,14,16)(H,17,19)
• InChIKey: AMHQGUWEVRTTJB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-N'-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-1,3-thiazole-5-carbohydrazide
• IUPAC Traditional name: 2-amino-N'-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-methyl-1,3-thiazole-5-carbohydrazide
• Synonyms: 2-Amino-N′-(4-hydroxy-3-methoxybenzylidene)-4-methyl-1,3-thiazole-5-carbohydrazide; 5-Thiazolecarboxylic acid, 2-amino-4-methyl-, 2-[(4-hydroxy-3-methoxyphenyl)methylene]hydrazide; OM137

Database IDs

• CAS Number: 292170-13-9
• MDL Number: MFCD02086738
• PubChem SID: 162248659
• PubChem CID: 5932799

CALCULATED PROPERTIES

• Acid pKa: 9.537589
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.2781603
• LogD (pH = 7.4): 1.2767098
• Log P: 1.2798246
• Molar Refractivity: 80.4373 cm^3
• Polarizability: 29.232449 Å^3
• Polar Surface Area: 109.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥95% (NMR)
• Empirical Formula (Hill Notation): C13H14N4O3S

DETAILS

Sigma Aldrich - O8140

Biochem/physiol Actions
OM137 is an inhibitor of aurora kinases; inhibitor of spindle checkpoint. OM137 is an aminothiazole derivative, which functions to override the spindle checkpoint primarily through inhibition of the Aurora kinases (mitotic kinases). OM137 is a more potent inhibitor of Aurora B compared with Aurora A in vitro, consistent with the effects of OM137 on checkpoint function in living cells. The compound has some CDK1 inhibitory activity, but is likely that the major mode by which OM137 drives mitotic exit of cells arrested in M phase via the spindle checkpoint is through its inhibitory activity against Aurora B kinase. The compound is less potent than N-[4-[(6,7-Dimethoxy-4-quinazolinyl)amino]phenyl]benzamide hydrochloride (Sigma Cat. D6068), which is more suited for in vitro testing due to low solubility and high serum binding. OM137 is less potent than selective Aurora A inhibitor, cyclopropanecarboxylic acid {3-[4-(3-trifluoromethyl-phenylamino)-pyrimidin-2-ylamino]-phenyl}-amide (Sigma Cat. C2368).