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865783-99-9

865783-99-9 Structure

865783-99-9 Structure
IdentificationBack Directory
[Name]

Phenol, 2-Methoxy-5-[[[(1E)-2-(2,4,6-triMethoxyphenyl)ethenyl]sulfonyl]Methyl]-, 1-(dihydrogen phosphate)
[CAS]

865783-99-9
[Synonyms]

CS-2580
ON-014185
Briciclib, >98%
Briciclib,ON-014185
Briciclib(ON 013105,ON 014185)
ON013105;ON014185;ON-013105;ON-014185
(E)-5-[[(2,4,6-Trimethoxystyryl)sulfonyl]methyl]-2-methoxyphenyl dihydrogen phosphate
2-Methoxy-5-({[(E)-2-(2,4,6-trimethoxyphenyl)vinyl]sulfonyl}methy l)phenyl dihydrogen phosphate
Phenol, 2-Methoxy-5-[[[(1E)-2-(2,4,6-triMethoxyphenyl)ethenyl]sulfonyl]Methyl]-, 1-(dihydrogen phosphate)
[Molecular Formula]

C19H23O10PS
[MDL Number]

MFCD22665751
[MOL File]

865783-99-9.mol
[Molecular Weight]

474.42
Chemical PropertiesBack Directory
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

DMF: 30 mg/ml; DMSO: 30 mg/ml
[form ]

A crystalline solid
[color ]

White to off-white
[InChI]

InChI=1S/C19H23O10PS/c1-25-14-10-17(27-3)15(18(11-14)28-4)7-8-31(23,24)12-13-5-6-16(26-2)19(9-13)29-30(20,21)22/h5-11H,12H2,1-4H3,(H2,20,21,22)/b8-7+
[InChIKey]

LXENKEWVEVKKGV-BQYQJAHWSA-N
[SMILES]

C1(OP(O)(O)=O)=CC(CS(/C=C/C2=C(OC)C=C(OC)C=C2OC)(=O)=O)=CC=C1OC
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Hazard InformationBack Directory
[Description]

Briciclib is a water soluble derivative of ON 013100, a small molecule that binds to and inhibits eukaryotic translation initiation factor 4E (eIF4E). Briciclib inhibits proliferation of JEKO-1 and Mino mantle cell leukemia (MCL), MCF-7 and MDA-MB-231 breast, AGS gastric, and OE19, OE33, and LFO-1 esophageal cancer cell lines with GI50 values ranging from 9.8 to 12.2 nM. It reduces expression of cyclin D1 and c-Myc, markers of eIF4E activity, in breast and MCL cancer cell lines in a dose-dependent manner. Briciclib also induces expression of the pro-apoptotic proteins p53 and cleaved caspase-3.
[Uses]

Briciclib is a useful organic intermediate employed in the synthesis of [[(phenylmethyl)sulfonyl]ethenyl]benzene derivatives with anticancer activity.
[IC 50]

eIF4
[storage]

Store at -20°C
[References]

[1] NEEL JASANI. Abstract 1649: Potent anticancer activity of an orally bioavailable small molecule, ON 013100, and its water soluble derivative, briciclib, a clinical-stage eIF4E-targeted agent[J]. Cancer research, 2015, 75 1: 1649-1649. DOI: 10.1158/1538-7445.am2015-1649
Spectrum DetailBack Directory
[Spectrum Detail]

Phenol, 2-Methoxy-5-[[[(1E)-2-(2,4,6-triMethoxyphenyl)ethenyl]sulfonyl]Methyl]-, 1-(dihydrogen phosphate)(865783-99-9)1HNMR
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