3-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-5-bromo-3-hydroxy-1,3-dihydro-2H-indol-2-one
Basic information
- CAS
258264-62-9- Standard SMILES
O=C(CC1(O)C(=O)Nc2ccc(Br)cc21)c1ccc2c(c1)OCO2- InChIKey
WFYHAKOLBICHEZ-UHFFFAOYSA-N- Molecular formula
- C17H12BrNO5
- Average molar mass
- 390.2 g/mol
- Monoisotopic mass
- 388.98989
Names & identifiers
- Preferred name
- 3-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-5-bromo-3-hydroxy-1,3-dihydro-2H-indol-2-one
- IUPAC
- 3-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-5-bromo-3-hydroxy-1H-indol-2-one
- English name
- S 12
- Molecular formula
- C17H12BrNO5
- Molecular weight
- 390.18
Names & synonyms
258264-62-9S 123-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-5-bromo-3-hydroxy-1,3-dihydro-2H-indol-2-oneNSC2016303-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-5-bromo-3-hydroxy-1H-indol-2-oneMLS000029787MFCD00117860SMR0000100183-[2-(1,3-benzodioxol-5-yl)-2-oxo-ethyl]-5-bromo-3-hydroxy-indolin-2-one3-(2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl)-5-bromo-3-hydroxyindolin-2-one3-(2-Benzo[1,3]dioxol-5-yl-2-oxo-ethyl)-5-bromo-3-hydroxy-1,3-dihydro-indol-2-one3-(2-(1,3-Benzodioxol-5-yl)-2-oxoethyl)-5-bromo-3-hydroxy-1,3-dihydro-2H-indol-2-one
Show more names
Survivin Antagonist, S122H-Indol-2-one, 3-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-5-bromo-1,3-dihydro-3-hydroxy-
Survivin inhibitor S12Maybridge1_002495C17H12BrNO5Oprea1_491740Oprea1_508702DivK1c_001247cid_304906SCHEMBL5548139
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 84.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 543
Physicochemical properties
- Boiling point
- 646.1 · 646.1±55.0 °C(Predicted)
- Density
- 1.69 · 1.690±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 50 mg/mL, · DMSO: 50mg/mL, nearly colorless
- form
- solid
- pka
- 11.17 · 11.17±0.20(Predicted)
- color
- white
- InChI
- 1S/C17H12BrNO5/c18-10-2-3-12-11(6-10)17(22,16(21)19-12)7-13(20)9-1-4-14-15(5-9)24-8-23-14/h1-6,22H,7-8H2,(H,19,21)
- InChIKey
- WFYHAKOLBICHEZ-UHFFFAOYSA-N
- SMILES
- O=C(CC1(C(C=C(Br)C=C2)=C2NC1=O)O)C3=CC(OCO4)=C4C=C3
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
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
UsesA cell-permeable hydroxyindolinone compound that acts as a selective antagonist of survivin. Induces mitotic arrest and blocks cell cycle at G2/M phase (~40 µM in HeLA cells) leading to apoptotic cell death. Shown to bind to a specific cavity adjacent to the interface involved in the dimerization of survivin. Binding is specific only to native survivin and does not affect any mutant forms. Inhibits HCT116 cell proliferation independently of their p53 status and reduces tumor volume in xenograft models in a dose-dependent manner (5 to 15 mg/kg).
Related reactions
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Compound notes
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