2-[(3,4-dihydroxyphenyl)methylidene]propanedinitrile

• ChemBase ID: 105107
• Molecular Formular: C10H6N2O2
• Molecular Mass: 186.16684
• Monoisotopic Mass: 186.04292744
• SMILES: Oc1c(O)cc(cc1)C=C(C#N)C#N
• Canonical SMILES: N#CC(=Cc1ccc(c(c1)O)O)C#N
• InChI: InChI=1S/C10H6N2O2/c11-5-8(6-12)3-7-1-2-9(13)10(14)4-7/h1-4,13-14H
• InChIKey: VTJXFTPMFYAJJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3,4-dihydroxyphenyl)methylidene]propanedinitrile
• IUPAC Traditional name: 2-[(3,4-dihydroxyphenyl)methylidene]propanedinitrile
• Synonyms: (3,4-Dihydroxybenzylidene)malononitrile; Tyrphostin 23; AG 18 (Tyrphostin 23); (3,4-Dihydroxybenzylidene)-malononitrile, RG-50810; Tyrphostin 23; RG-50810; TYRPHOSTIN A23

Database IDs

• CAS Number: 118409-57-7
• MDL Number: MFCD00133899
• PubChem SID: 24278041; 162092168
• PubChem CID: 2052

CALCULATED PROPERTIES

• Acid pKa: 7.6317396
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5622566
• LogD (pH = 7.4): 1.3666905
• Log P: 1.5654298
• Molar Refractivity: 51.0546 cm^3
• Polarizability: 18.43874 Å^3
• Polar Surface Area: 88.04 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; DMF; DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 237-239°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Store in refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: EGFR
• Gene Information: human ... CDK2(1017)

Product Information

• Purity: >99%; ≥98%
• Salt Data: Free Base
• Potency: 35 μM IC50

DETAILS

MP Biomedicals - 02158820

Purity: >99%
A potent inhibitor of EGF receptor kinase activity^1,2,3 .

Sigma Aldrich - T7165

Biochem/physiol Actions
EGFR tyrosine kinase inhibitor.

Toronto Research Chemicals - T923000

A specific inhibitor for the epidermal growth factor receptor. Also inhibits EGF-dependent cell proliferation (IC50=35uM).

REFERENCES

• Gazit, A., et al., J. Med. Chem. , 32 : 2344, (1989).
• Lyall, R.M., et al., J. Biol. Chem. , 264 : 14503, (1989).
• Yaish, P., et al., Science , 242 : 933, (1988).
• Lyall, R. M., et al.: J. Biol. Chem., 264, 14503 (1989)
• Bryckaert, M.C., et al.: Exp. Cell Res., 199, 255 (1992)