1147-56-4

Basic information

• Product Name: 1-(2-THIAZOLYLAZO)-2-NAPHTHOL
• Synonyms: TAN;1-(2’-Thiazolylazo)-β-naphtho;1-(2-thiazolylazo)-2-naphthaleno;1-(2-thiazolylazo)-2-Naphthalenol;2-(2-HYDROXY-1-NAPHTHYLAZO)THIAZOLE;1-(2-THIAZOLYLAZO)-2-NAPHTHOL;1-(thiazol-2-ylazo)-2-naphthol;1-(2'-Thiazolylazo)-β-naphthol
• CAS NO: 1147-56-4
• Molecular Formula: C₁₃H₉N₃OS
• Molecular Weight: 255.3
• EINECS: 214-555-3
• Product Categories: Analytical Chemistry;Azo Compounds;Chelating Reagents;Naphthylazo Compounds
• Mol File: 1147-56-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 138-139 °C
• Boiling Point: 464.8 °C at 760 mmHg
• Flash Point: 234.9 °C
• Appearance: powder
• Density: 1.40
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: 2-8°C
• Solubility: methanol: 10 mg/mL, clear
• PKA: 8.71±0.50(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• BRN: 223783
• CAS DataBase Reference: 1-(2-THIAZOLYLAZO)-2-NAPHTHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-THIAZOLYLAZO)-2-NAPHTHOL(1147-56-4)
• EPA Substance Registry System: 1-(2-THIAZOLYLAZO)-2-NAPHTHOL(1147-56-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1147-56-4(Hazardous Substances Data)

Usage

Description

ERGi-USU (1147-56-4) selectively inhibits the growth of ERG-positive VCaP prostate cancer cells, COLO320 colon cancer cells, KG-1 and MOLT-4 leukemia cells with minimal effect on ERG-negative cells or normal prostate or endothelial cells (IC50 = 169 nM for cell growth and 315 nM for ERG protein in VCaP cells). It selectively inhibits the kinase RIOK2 (Kd = 200 nM) causing disruption of ribosomal biogenesis and ribosomal stress.

Uses

1-(2-Thiazolylazo)-2-naphthol is a high affinity Rio Kinase 2 (RIOK2) inhibitor (Kd = 200 nM). Exhibits >6-fold selectivity for RIOK2 over a panel of 456 kinases. Inhibits ERG protein and potently inhibits growth of ERG-positive VCaP prostate cancer cells in vitro (IC50 = 169 nM) but not ERG-negative cell lines. Also inhibits growth of VCaP xenografts in mice.

References

1) Mohamed et al. (2018), Identification of a Small Molecule That Selectively Inhibits ERG-Positive Cancer Cell Growth; Cancer Res. 78 3659

InChI:InChI=1/C13H9N3OS/c17-11-6-5-9-3-1-2-4-10(9)12(11)15-16-13-14-7-8-18-13/h1-8H,(H,14,16)/b15-12-

Upstream product

• 96-50-4 2-thiazolylamine 
• 135-19-3 β-naphthol 

Downstream Products

• 1638770-49-6 naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazin-4-ium tosylate 
• 65149-48-6 8,8-diphenyl-8λ⁵-naphtho[1',2':4,5][1,3,2]oxazaphospholo[3,2-b]thiazolo[3,2-d][1,2,4,3]triazaphosphole 
• 65149-51-1 8,8-diphenoxy-8λ⁵-naphtho[1',2':4,5][1,3,2]oxazaphospholo[3,2-b]thiazolo[3,2-d][1,2,4,3]triazaphosphole 

Relevant articles and documents

Formation of azolo [1,2,4]triazinium salts by reaction of heterocyclic-substituted 1-azo-naphthalen-2-ols with strong acids

By reaction of heterocyclic-substituted 1-azo-naphth-2-ols with the Vilsmeier reagent or with strong acids polycyclic azolo[1,2,4]triazinium salts are formed in good yields. The azolo[1,2,4] triazinium salts exhibit similar UV/Vis absorption properties as the starting azo compounds, but in contrast to those the fluorescence appears in the visible range.