Briciclib

Base Information

• Chemical Name: Briciclib
• CAS No.: 865783-99-9
• Molecular Formula: C₁₉H₂₃O₁₀PS
• Molecular Weight: 474.425
• UNII: WG93X96336
• ChEMBL ID: CHEMBL1206245
• Metabolomics Workbench ID: 153069
• NCI Thesaurus Code: C141431
• Wikidata: Q27292622
• Mol file: 865783-99-9.mol

Synonyms:Briciclib;865783-99-9;ON-014185;Briciclib (ON-013105);ON 014185;Briciclib (ON-014185);865783-99-9 (free acid);(E)-2-Methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl dihydrogen phosphate;WG93X96336;Phenol, 2-methoxy-5-[[[(1E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl]methyl]-, 1-(dihydrogen phosphate);Phenol, 2-methoxy-5-((((1E)-2-(2,4,6-trimethoxyphenyl)ethenyl)sulfonyl)methyl)-, 1-(dihydrogen phosphate);Briciclib [USAN:INN];ON-013105;UNII-WG93X96336;Briciclib [USAN];BRICICLIB [INN];Briciclib (USAN/INN);BRICICLIB [WHO-DD];SCHEMBL1634579;SCHEMBL1634581;CHEMBL1206245;LXENKEWVEVKKGV-BQYQJAHWSA-N;AMY42169;BCP17292;EX-A2492;MFCD22665751;s6533;AKOS027439966;CS-5589;DB12004;AC-36098;HY-16366;ON014185;Briciclib(ON 013105,ON 014185);Briciclib(ON 013105,ON 014185)?;NS00071861;D10614;Q27292622;(2-methoxy-5-{[(E)-2-(2,4,6-trimethoxyphenyl)ethenesulfonyl]methyl}phenoxy)phosphonic acid;(e)-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl dihydrogen phosphate;ON013105;ON 013105;(E)-5-(((2,4,6-TRIMETHOXYSTYRYL)SULFONYL)METHYL)-2-METHOXYPHENYL DIHYDROGEN PHOSPHATE;[2-methoxy-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]phenyl] dihydrogen phosphate;2-Methoxy-5-(((2-(2,4,6-trimethoxyphenyl)ethenyl)sulfonyl)methyl)phenyl dihydrogen phosphate;Phenol, 2-Methoxy-5-[[[(1E)-2-(2,4,6-triMethoxyphenyl)ethenyl]sulfonyl] Methyl]-, 1-(dihydrogen phosphate)

Chemical Property of Briciclib

Chemical Property:

• PSA: 156.01000
• LogP: 3.85900
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 474.07495510
• Heavy Atom Count: 31
• Complexity: 717

Purity/Quality:

98% min ^*data from raw suppliers

Briciclib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CS(=O)(=O)C=CC2=C(C=C(C=C2OC)OC)OC)OP(=O)(O)O
• Isomeric SMILES: COC1=C(C=C(C=C1)CS(=O)(=O)/C=C/C2=C(C=C(C=C2OC)OC)OC)OP(=O)(O)O
• Recent ClinicalTrials: Dose-escalation, Safety and Pharmacokinetic Study of Briciclib in Advanced Solid Tumors
• 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.

Technology Process of Briciclib

There total 10 articles about Briciclib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.3%

(E)-2,4,6-trimethoxystyryl-3-O-bis(benzyl)phosphoryl-4-methoxybenzylsulfone (865784-00-5) → ON-013105 (865783-99-9)

Guidance literature:

(E)-2,4,6-trimethoxystyryl-3-O-bis(benzyl)phosphoryl-4-methoxybenzylsulfone; With trimethylsilyl bromide; In dichloromethane; at 0 ℃; for 0.75h;

With sodium thiosulfate; In dichloromethane; for 0.0833333h; Further stages.;

DOI:10.1021/jm701077b

Reference yield:

C19H21Cl2O8PS → ON-013105 (865783-99-9)

Guidance literature:

With water; In tetrahydrofuran; Cooling with ice;

Reference yield:

isovanillin (621-59-0) → ON-013105 (865783-99-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C

1.2: 12.5 - 16.5 h

2.1: sodium tetrahydroborate / methanol / 0.5 h / 0 - 20 °C

2.2: 0 °C

3.1: thionyl chloride / benzene / 0.17 h / 0 °C

4.1: sodium hydroxide / methanol / 0.17 h

4.2: 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

6.1: dihydrogen peroxide; acetic acid / water / 20 °C

7.1: piperidine; benzoic acid / toluene / 2 - 3 h / Heating / reflux

8.1: carbon tetrabromide; triethylamine / acetonitrile / 0.17 h / 0 °C

8.2: 2 h / 0 °C

9.1: trimethylsilyl bromide / dichloromethane / 0.75 h / 0 °C

With piperidine; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; trimethylsilyl bromide; carbon tetrabromide; tetrabutyl ammonium fluoride; dihydrogen peroxide; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; benzoic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

upstream raw materials:

(E)-2,4,6-trimethoxystyryl-3-O-bis(benzyl)phosphoryl-4-methoxybenzylsulfone

isovanillin

(E)-5-((2,4,6-trimethoxystyrylsulfinyl)methyl)-2-methoxyphenol

3-hydroxy-4-methoxybenzylsulfonylacetic acid

Refernces

• 1、 Reddy, M. V. Ramana,Mallireddigari, Muralidhar R.,Cosenza, Stephen C.,Pallela, Venkat R.,Iqbal, Nabisa M.,Robell, Kimberly A.,Kang, Anthony D.,Reddy, E. Premkumar. "Design, synthesis, and biological evaluation of (E)-styrylbenzylsulfones as novel anticancer agents". . p. 86 - 100. Retrieved 2008/09/20.