Rigosertib

Base Information

• Chemical Name: Rigosertib
• CAS No.: 592542-59-1
• Molecular Formula: C21H25NO8S
• Molecular Weight: 451.497
• UNII: 67DOW7F9GL
• DSSTox Substance ID: DTXSID30207984
• Nikkaji Number: J2.499.043E
• Wikipedia: Rigosertib
• Wikidata: Q21099552
• NCI Thesaurus Code: C152216
• Pharos Ligand ID: 4ZD6QG18FGFT
• Metabolomics Workbench ID: 153189
• ChEMBL ID: CHEMBL1241855
• Mol file: 592542-59-1.mol

Synonyms:(N-(2-methyloxy-5-(2',4',6'-trimethoxystyrylsulfonyl)methylenephenyl)amino)acetic acid;N-(2-Methoxy-5-((((E)-2-(2,4,6-trimethoxyphenyl)vinyl)sulfonyl)methyl)phenyl)glycine;ON 01910;ON 01910.Na;ON-01910;ON01910;rigosertib;rigosertib sodium;sodium (N-(2-methyloxy-5-(2',4',6'-trimethoxystyrylsulfonyl)methylenephenyl)amino)acetate

Chemical Property of Rigosertib

Chemical Property:

• Melting Point: 172-174 °C(Solv: acetone (67-64-1))
• Boiling Point: 756.1±60.0 °C(Predicted)
• PKA: 4.23±0.20(Predicted)
• PSA: 128.77000
• Density: 1.332±0.06 g/cm3(Predicted)
• LogP: 3.95700
• Solubility.: Soluble in DMSO
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 451.13008793
• Heavy Atom Count: 31
• Complexity: 678

Purity/Quality:

97% ^*data from raw suppliers

Rigosertib ^*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)NCC(=O)O
• Isomeric SMILES: COC1=C(C=C(C=C1)CS(=O)(=O)/C=C/C2=C(C=C(C=C2OC)OC)OC)NCC(=O)O
• Recent ClinicalTrials: Rigosertib Plus Pembrolizumab in Treating Patients With Unresectable/Metastatic Melanoma Refractory to PD-1 Inhibitors
• Recent EU Clinical Trials: A Phase II, Open Study to Assess Efficacy and Safety of Rigosertib in Patients with Recessive Dystrophic Epidermolysis bullosa associated Locally Advanced/Metastatic Squamous Cell Carcinoma
• Uses: Rigosertib is a microtubule destabilizing agent which may be employed in the treatment of high-?risk myelodysplastic syndrome.

Technology Process of Rigosertib

There total 15 articles about Rigosertib 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: 80.0%

(E)-methyl 2-(2-methoxy-5-((2',4',6'-trimethoxystyrylsulfonyl)methyl)phenylamino)acetate (592542-61-5) → (E)-2-((2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl)amino)acetic acid (592542-59-1)

Guidance literature:

(E)-methyl 2-(2-methoxy-5-((2',4',6'-trimethoxystyrylsulfonyl)methyl)phenylamino)acetate; With sodium hydroxide; ethanol; water; at 25 ℃; for 138795h; Heating / reflux;

With hydrogenchloride; water; In ethanol; at 25 ℃;

Reference yield:

3-nitro-4-methoxybenzyl bromide (61010-34-2) → (E)-2-((2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl)amino)acetic acid (592542-59-1)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium carbonate / methanol / 1 h / Reflux

2: dihydrogen peroxide / acetic acid / 6 h / 50 °C

3: piperidine / pyridine / 36 h / 20 °C

5: sodium acetate

6: water; sodium carbonate

With piperidine; water; dihydrogen peroxide; sodium acetate; sodium carbonate; In pyridine; methanol; acetic acid;

DOI:10.1016/j.bmcl.2011.03.041

Reference yield:

2-(4-methoxy-3-nitrobenzylthio)acetic acid (22216-44-0) → (E)-2-((2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl)amino)acetic acid (592542-59-1)

Guidance literature:

Multi-step reaction with 5 steps

1: dihydrogen peroxide / acetic acid / 6 h / 50 °C

2: piperidine / pyridine / 36 h / 20 °C

4: sodium acetate

5: water; sodium carbonate

With piperidine; water; dihydrogen peroxide; sodium acetate; sodium carbonate; In pyridine; acetic acid;

DOI:10.1016/j.bmcl.2011.03.041

upstream raw materials:

(E)-methyl 2-(2-methoxy-5-((2',4',6'-trimethoxystyrylsulfonyl)methyl)phenylamino)acetate

2-(4-methoxy-3-nitrobenzylthio)acetic acid

C₂₃H₂₉NO₈S

(E)-2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)aniline

Downstream raw materials:

2-((2-methoxy-5-(((2,4,6-trimethoxyphenethyl)sulfonyl)methyl)phenyl)amino)acetic acid