4-{[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino}phenol

• ChemBase ID: 153993
• Molecular Formular: C15H11ClN2OS
• Molecular Mass: 302.77864
• Monoisotopic Mass: 302.02806166
• SMILES: c1cc(ccc1c1csc(n1)Nc1ccc(cc1)O)Cl
• Canonical SMILES: Oc1ccc(cc1)Nc1scc(n1)c1ccc(cc1)Cl
• InChI: InChI=1S/C15H11ClN2OS/c16-11-3-1-10(2-4-11)14-9-20-15(18-14)17-12-5-7-13(19)8-6-12/h1-9,19H,(H,17,18)
• InChIKey: ZFGXZJKLOFCECI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino}phenol
• IUPAC Traditional name: 4-{[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino}phenol
• Synonyms: 4-[[4-(4-Chlorophenyl)-2-thiazolyl]amino]phenol; SKI II; SphK-I2; Sphingosine Kinase Inhibitor 2; SKI II

Database IDs

• CAS Number: 312636-16-1
• MDL Number: MFCD00733553
• PubChem SID: 24724614; 162248132
• PubChem CID: 753704

CALCULATED PROPERTIES

• Acid pKa: 10.279664
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.0893874
• LogD (pH = 7.4): 5.0891953
• Log P: 5.0897694
• Molar Refractivity: 80.7758 cm^3
• Polarizability: 32.237606 Å^3
• Polar Surface Area: 45.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: off-white solid

Safety Information

• Storage Condition: protect from light
• 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: S1P Receptor

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H11ClN2OS

DETAILS

Sigma Aldrich - S5696

Other Notes
Product is air and light sensitive
Biochem/physiol Actions
Sphingosine kinase (SK) plays a pivotal role in regulating tumor growth and SK can act as an oncogene. Expression of SK RNA is significantly elevated in a variety of solid tumors, compared with normal tissue from the same patient. A number of novel inhibitors of human SK were identified, and several representative compounds were characterized in detail. These compounds demonstrated activity at sub- to micromolar concentrations, making them more potent than any other reported SK inhibitor, and were selective toward SK compared with a panel of human lipid and protein kinases. Kinetic studies revealed that the compounds were not competitive inhibitors of the ATP-binding site of SK. 4-[4-(4-chloro-phenyl)-thiazol-2-ylamino]-phenol (SKI-II) inhibitor is orally bioavailable, detected in the blood for at least 8 h, and showed a significant inhibition of tumor growth in mice with IC50 = 0.5 μM; SKI II does not act at ATP-binding site. Displays no inhibition of ERK2, PI 3-kinase, or PKCa at concentrations up to 60 μM.SKI II induces apoptosis and inhibits proliferation in several other tumor cell lines in vitro (IC50 = 0.9-4.6 μM).