1-(2-Thiazolylazo)-2-naphthol
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Basic information
- CAS
1147-56-4- Standard SMILES
Oc1ccc2ccccc2c1N=Nc1nccs1- InChIKey
IOMXCGDXEUDZAK-UHFFFAOYSA-N- Molecular formula
- C13H9N3OS
- Average molar mass
- 255.3 g/mol
- Monoisotopic mass
- 255.04663309
Overview
NSC139021 is a highly selective inhibitor for the growth of ERG-positive cancer cells.(MedChemExpress).
Names & identifiers
- Preferred name
- 1-(2-Thiazolylazo)-2-naphthol
- IUPAC
- 1-(1,3-thiazol-2-yldiazenyl)naphthalen-2-ol
- English name
- 1-(2-THIAZOLYLAZO)-2-NAPHTHOL
- Molecular formula
- C13H9N3OS
- Molecular weight
- 255.3
Names & synonyms
1147-56-41-(2-Thiazolylazo)-2-naphtholERGi-USUNSC1390212-Naphthalenol, 1-(2-thiazolylazo)-1-(2-Thiazoylazo)-2-naphthol2-Naphthol, 1-(2-thiazolylazo)-MLS0007382801-[2-(1,3-thiazol-2-yl)diazen-1-yl]naphthalen-2-ol1-[2-(2-Thiazolyl)diazenyl]-2-naphthalenolMFCD000216112-Naphthalenol, 1-[2-(2-thiazolyl)diazenyl]-
Show more names
TANNitrilotantalum(III)NSC139021 (ERGi-USU)ERGi-USU (NSC139021)ERGi-USU, 10 mM in DMSO1-(2’-Thiazolylazo)-β-naphtho1-(thiazol-2-ylazo)-2-naphthol
61433-07-6CHEMBL20943831-(1,3-thiazol-2-yldiazenyl)naphthalen-2-ol1-(Thiazol-2-yldiazenyl)naphthalen-2-olSMR000528601(E)-1-(thiazol-2-yldiazenyl)naphthalen-2-olTAN [=1-(2-THIAZOLYLAZO)-2-NAPHTHOL] [SPECTROPHOTOMETRIC REAGENT FOR TRANSITION METALS]2-Naphthalenol, 1-(2-(2-thiazolyl)diazenyl)-
Database identifiers
- CAS
1147-56-4- PubChem CID
- 93572
- DTXSID
DTXSID7061566- ChEMBL
CHEMBL1511179、CHEMBL2094383- ChEBI
CHEBI:232634- Nikkaji
- J7.283D
Properties
Computed structural propertiesFilling in
- XLogP
- 4
- Topological polar surface area
- 86.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 313
Physicochemical properties
- Melting point
- 138 · 138-139 °C
- Boiling point
- 464.8 · 464.8±47.0 °C(Predicted)
- Density
- 1.4 · 1.40
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL, · methanol: 10 mg/mL, clear
- pka
- 8.71 · 8.71±0.50(Predicted)
- form
- solid
- color
- Red or orange
- BRN
- 223783 · 223783
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
- InChI
- 1S/C13H9N3OS/c17-11-6-5-9-3-1-2-4-10(9)12(11)15-16-13-14-7-8-18-13/h1-8,17H
- InChIKey
- IOMXCGDXEUDZAK-UHFFFAOYSA-N
- SMILES
- [s]1c(ncc1)N=Nc2c3c(ccc2O)cccc3
- CAS DataBase Reference
- 1147 · 1147-56-4(CAS DataBase Reference)
- EPA Substance Registry System
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 2927.00.5000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
DescriptionERGi-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.
Uses1-(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.
Related reactions
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Compound notes
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