N-[3,6-bis[(3,5-dimethylpiperidin-1-yl)sulfonyl]-10-nitrosoanthracen-9-yl]hydroxylamine
Basic information
- CAS
1227637-23-1- Standard SMILES
CC1CC(C)CN(S(=O)(=O)c2ccc3c(NO)c4ccc(S(=O)(=O)N5CC(C)CC(C)C5)cc4c(N=O)c3c2)C1- InChIKey
OMWCXCBGEFHCTN-UHFFFAOYSA-N- Molecular formula
- C28H36N4O6S2
- Average molar mass
- 588.7 g/mol
- Monoisotopic mass
- 588.20762723
Overview
Tegavivint is a small molecule inhibitor of the Wnt/beta-catenin pathway with potential antineoplastic activity. Upon intravenous administration, tegavivint binds to transducin beta-like protein 1 (TBL1) and disrupts the binding of beta-catenin to TBL1. This promotes beta-catenin degradation, attenuates nuclear and cytoplasmic levels of beta-catenin, and reduces transcriptional activity of transcription factor 4 (TCF4) and expression of its target genes, cyclin D1, c-Myc and survivin. The Wnt/beta-catenin signaling pathway regulates cell morphology, motility, and proliferation; aberrant regulation of this pathway leads to neoplastic proliferation. Beta-catenin is frequently mutated in various tumors.
Names & identifiers
- Preferred name
- N-[3,6-bis[(3,5-dimethylpiperidin-1-yl)sulfonyl]-10-nitrosoanthracen-9-yl]hydroxylamine
- IUPAC
- N-[3,6-bis[(3,5-dimethylpiperidin-1-yl)sulfonyl]-10-nitrosoanthracen-9-yl]hydroxylamine
- English name
- BC2059
- Molecular formula
- C28H36N4O6S2
- Molecular weight
- 588.74
Names & synonyms
TegavivintTegatrabetan (BC-2059)SCHEMBL13366899SCHEMBL29489537S0733Tegoprazan D6BC2059BC-2059 Te atrabetanTegatrabetan (BC2059)BC-2059BC2059Tegatrabetan, 10 mM in DMSO
Show more names
Tegatrabetan (BC-2059) ，S0733TEGATRABETANBC-2059Tegatrabetan,inhibit,Inhibitor,β-catenin,BC-2059,Beta catenin,BC 2059
Database identifiers
- CAS
1227637-23-1- PubChem CID
- 46212394
- ChEMBL
CHEMBL3601411
Properties
Computed structural properties
- XLogP
- 5
- Topological polar surface area
- 153 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 1,020
Physicochemical properties
- Melting point
- 287 °C · 287 °C(Solvent: Dichloromethane; Hexane)
- Boiling point
- 757.6 · 757.6±70.0 °C(Predicted)
- Density
- 1.46 · 1.46±0.1 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- 125 mg/mL · DMSO: 125 mg/mL (212.32 mM)
- pka
- 10.07 · 10.07±0.20(Predicted)
- form
- Solid
- color
- White to light yellow
- InChIKey
- LQQUOMJXUXVPRB-IOTKHNBZSA-N
- SMILES
- [S](=O)(=O)(N5C[C@H](C[C@H](C5)C)C)c1cc2c(cc1)C(c3c(cc(cc3)[S](=O)(=O)N4C[C@H](C[C@H](C4)C)C)C2N=O)N=O
- FDA UNII
- 18 AP231HUP · 18AP231HUP
- NCI Drug Dictionary
- tegavivint
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- WGK Germany
- 3 · WGK 3
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
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesTegatrabetan (BC2059) is a β-Catenin antagonist. Tegatrabetan disrupts the binding of β-catenin with the scaffold protein transducin β-like 1 (TBL1)[1].
Related reactions
0 records
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Compound notes
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