2-[4-(4-chlorophenoxy)phenyl]-1H-1,3-benzodiazole-5-carboxamide

• ChemBase ID: 153932
• Molecular Formular: C20H14ClN3O2
• Molecular Mass: 363.79706
• Monoisotopic Mass: 363.07745438
• SMILES: c1cc(ccc1c1[nH]c2ccc(cc2n1)C(=O)N)Oc1ccc(cc1)Cl
• Canonical SMILES: Clc1ccc(cc1)Oc1ccc(cc1)c1nc2c([nH]1)ccc(c2)C(=O)N
• InChI: InChI=1S/C20H14ClN3O2/c21-14-4-8-16(9-5-14)26-15-6-1-12(2-7-15)20-23-17-10-3-13(19(22)25)11-18(17)24-20/h1-11H,(H2,22,25)(H,23,24)
• InChIKey: UXGJAOIJSROTTN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(4-chlorophenoxy)phenyl]-1H-1,3-benzodiazole-5-carboxamide
• IUPAC Traditional name: 2-[4-(4-chlorophenoxy)phenyl]-1H-1,3-benzodiazole-5-carboxamide
• Synonyms: 2-(4-(4-Chlorophenoxy)phenyl)-1H-benzimidazole-5-carboxamide hydrate; Chk2 Inhibitor II hydrate

Database IDs

• CAS Number: 516480-79-8(anhydrous)
• MDL Number: MFCD08276917
• PubChem SID: 162248071; 24724438
• PubChem CID: 9969021

CALCULATED PROPERTIES

• Acid pKa: 11.079576
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 4.2073007
• LogD (pH = 7.4): 4.2387486
• Log P: 4.2392464
• Molar Refractivity: 110.1941 cm^3
• Polarizability: 39.92895 Å^3
• Polar Surface Area: 81.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white to tan solid

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CHEK2(11200)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H14ClN3O2 · xH2O

DETAILS

Sigma Aldrich - C3742

Biochem/physiol Actions
Chk2 Inhibitor II is a checkpoint kinase 2 inhibitor, which controls the p53 response to DNA breaks induced by radiation, leading to apoptosis. Protection of T-cells from apoptosis implies use as an adjuvant for radiation therapy in cancer. IC50 = 15 nM; Ki = 37 nM. Chk2 Inhibitor II shows 1000-fold greater selectivity for the Chk2 serine/threonine kinase than for the Cdk1/B and CK1 kinases (for which IC50 = 12 μM and 17 μM, respectively). Chk2 Inhibitor II weakly inhibits a panel of 31 other kinases (<25% inhibition at a concentration of 10 μM and prevents apoptosis of human CD4+ and CD8+ T-cells subjected to ionizing radiation (EC50 = 3 μM and 7.6 μM, respectively).