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592542-59-1,MFCD09038489
Catalog No.:AA003947

592542-59-1 | Rigosertib

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25mg
98%
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$248.00   $174.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003947
Chemical Name:
Rigosertib
CAS Number:
592542-59-1
Molecular Formula:
C21H25NO8S
Molecular Weight:
451.4901
MDL Number:
MFCD09038489
SMILES:
COc1cc(OC)cc(c1/C=C/S(=O)(=O)Cc1ccc(c(c1)NCC(=O)O)OC)OC
Properties
Computed Properties
 
Complexity:
678  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
11  
XLogP3:
2.5  

Downstream Synthesis Route
1310-73-2    592542-59-1   
sodium(E)-2-(2-methoxy-5-((2',4',6'-trimethoxystyrylsulfonyl)methyl)phenylamino)acetate 

[1]CurrentPatentAssignee:ICAHNSCHOOLOFMEDICINEATMOUNTSINAI-WO2008/27049,2008,A1Locationinpatent:Page/Pagecolumn33

592542-59-1   
sodium(E)-2-(2-methoxy-5-((2',4',6'-trimethoxystyrylsulfonyl)methyl)phenylamino)acetate 

[1]CurrentPatentAssignee:ICAHNSCHOOLOFMEDICINEATMOUNTSINAI-WO2006/104668,2006,A2Locationinpatent:Page/Pagecolumn38

[2]CurrentPatentAssignee:ICAHNSCHOOLOFMEDICINEATMOUNTSINAI-US2010/305059,2010,A1

[1]CurrentPatentAssignee:ICAHNSCHOOLOFMEDICINEATMOUNTSINAI-WO2008/27049,2008,A1Locationinpatent:Page/Pagecolumn29

[2]CurrentPatentAssignee:ICAHNSCHOOLOFMEDICINEATMOUNTSINAI-WO2006/104668,2006,A2Locationinpatent:Page/Pagecolumn32

[3]Locationinpatent:experimentalpartReddy,M.V.Ramana;Venkatapuram,Padmavathi;Mallireddigari,MuralidharR.;Pallela,VenkatR.;Cosenza,StephenC.;Robell,KimberlyA.;Akula,Balaiah;Hoffman,BenjaminS.;Reddy,E.Premkumar[JournalofMedicinalChemistry,2011,vol.54,#18,p.6254-6276]

592542-61-5    592542-59-1   
(E)-2,4,6-trimethoxystyryl-3-(carboxymethylamino)-4-methoxybenzylsulfone 

[1]CurrentPatentAssignee:ICAHNSCHOOLOFMEDICINEATMOUNTSINAI-US2010/305059,2010,A1

(E)-2',4',6'-trimethoxystyryl-4-methoxy-3-nitrobenzylsulfone 
  592542-59-1 

[1]Chahrour,Osama;Abdalla,Ashraf;Lam,Frankie;Midgley,Carol;Wang,Shudong[BioorganicandMedicinalChemistryLetters,2011,vol.21,#10,p.3066-3069]

[2]Reddy,M.V.Ramana;Venkatapuram,Padmavathi;Mallireddigari,MuralidharR.;Pallela,VenkatR.;Cosenza,StephenC.;Robell,KimberlyA.;Akula,Balaiah;Hoffman,BenjaminS.;Reddy,E.Premkumar[JournalofMedicinalChemistry,2011,vol.54,#18,p.6254-6276]

Literature

Title: ON 01910.Na inhibits growth of diffuse large B-cell lymphoma by cytoplasmic sequestration of sumoylated C-MYB/TRAF6 complex.

Journal: Translational research : the journal of laboratory and clinical medicine 20160901

Title: A phase II/III randomized study to compare the efficacy and safety of rigosertib plus gemcitabine versus gemcitabine alone in patients with previously untreated metastatic pancreatic cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20150901

Title: Efficacy of the polo-like kinase inhibitor rigosertib, alone or in combination with Abelson tyrosine kinase inhibitors, against break point cluster region-c-Abelson-positive leukemia cells.

Journal: Oncotarget 20150821

Title: Clinical activity and safety of the dual pathway inhibitor rigosertib for higher risk myelodysplastic syndromes following DNA methyltransferase inhibitor therapy.

Journal: Hematological oncology 20150601

Title: Rigosertib induces cell death of a myelodysplastic syndrome-derived cell line by DNA damage-induced G2/M arrest.

Journal: Cancer science 20150301

Title: In vitro antitumor mechanism of (E)-N-(2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-yl)methanesulfonamide.

Journal: Molecular pharmacology 20150101

Title: Centmitor-1, a novel acridinyl-acetohydrazide, possesses similar molecular interaction field and antimitotic cellular phenotype as rigosertib, on 01910.Na.

Journal: Molecular cancer therapeutics 20140501

Title: Discovery of (E)-3-((styrylsulfonyl)methyl)pyridine and (E)-2-((styrylsulfonyl)methyl)pyridine derivatives as anticancer agents: synthesis, structure-activity relationships, and biological activities.

Journal: Journal of medicinal chemistry 20140327

Title: Phase I study of oral rigosertib (ON 01910.Na), a dual inhibitor of the PI3K and Plk1 pathways, in adult patients with advanced solid malignancies.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20140315

Title: Rigosertib as a selective anti-tumor agent can ameliorate multiple dysregulated signaling transduction pathways in high-grade myelodysplastic syndrome.

Journal: Scientific reports 20140101

Title: The dual pathway inhibitor rigosertib is effective in direct patient tumor xenografts of head and neck squamous cell carcinomas.

Journal: Molecular cancer therapeutics 20131001

Title: Phase I study of ON 01910.Na (Rigosertib), a multikinase PI3K inhibitor in relapsed/refractory B-cell malignancies.

Journal: Leukemia 20130901

Title: Phase I clinical trial of oral rigosertib in patients with myelodysplastic syndromes.

Journal: British journal of haematology 20130801

Title: A novel anti-tumor inhibitor identified by virtual screen with PLK1 structure and zebrafish assay.

Journal: PloS one 20130101

Title: Dissecting the phenotypes of Plk1 inhibition in cancer cells using novel kinase inhibitory chemical CBB2001.

Journal: Laboratory investigation; a journal of technical methods and pathology 20121001

Title: Directed therapy for patients with myelodysplastic syndromes (MDS) by suppression of cyclin D1 with ON 01910.Na.

Journal: Leukemia research 20120801

Title: Targeting cyclin D1 for high risk myelodysplastic syndromes.

Journal: Leukemia research 20120801

Title: Phase I study of Rigosertib, an inhibitor of the phosphatidylinositol 3-kinase and Polo-like kinase 1 pathways, combined with gemcitabine in patients with solid tumors and pancreatic cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120401

Title: ON 01910.Na is selectively cytotoxic for chronic lymphocytic leukemia cells through a dual mechanism of action involving PI3K/AKT inhibition and induction of oxidative stress.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120401

Title: Treatment of higher risk myelodysplastic syndrome patients unresponsive to hypomethylating agents with ON 01910.Na.

Journal: Leukemia research 20120101

Title: Application of a liquid chromatography-tandem mass spectrometry (LC/MS/MS) method to the pharmacokinetics of ON01910 in brain tumor-bearing mice.

Journal: Journal of pharmaceutical and biomedical analysis 20111215

Title: Failure of hypomethylating agent-based therapy in myelodysplastic syndromes.

Journal: Seminars in oncology 20111001

Title: Discovery of a clinical stage multi-kinase inhibitor sodium (E)-2-{2-methoxy-5-[(2',4',6'-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na): synthesis, structure-activity relationship, and biological activity.

Journal: Journal of medicinal chemistry 20110922

Title: Effect of ON 01910.Na, an anticancer mitotic inhibitor, on cell-cycle progression correlates with RanGAP1 hyperphosphorylation.

Journal: Cancer research 20110715

Title: Synthesis and biological evaluation of benzyl styrylsulfonyl derivatives as potent anticancer mitotic inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20110515

Title: Discontinuous drug binding to proteins: binding of an antineoplastic benzyl styryl sulfone to albumin and enzymes in vitro and in phase I clinical trials.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100901

Title: Preclinical pharmacokinetics and in vitro activity of ON 01910.Na, a novel anti-cancer agent.

Journal: Cancer chemotherapy and pharmacology 20091201

Title: Polo-like kinase (PLK) inhibitors in preclinical and early clinical development in oncology.

Journal: The oncologist 20090601

Title: Styryl sulfonyl compounds inhibit translation of cyclin D1 in mantle cell lymphoma cells.

Journal: Oncogene 20090326

Title: Evaluation of the novel mitotic modulator ON 01910.Na in pancreatic cancer and preclinical development of an ex vivo predictive assay.

Journal: Oncogene 20090129

Title: Phase I study of ON 01910.Na, a novel modulator of the Polo-like kinase 1 pathway, in adult patients with solid tumors.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20081201

Title: Validation and implementation of a liquid chromatography/tandem mass spectrometry assay to quantitate ON 01910.Na, a mitotic progression modulator, in human plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070901

Title: BI 2536, a potent and selective inhibitor of polo-like kinase 1, inhibits tumor growth in vivo.

Journal: Current biology : CB 20070220

Title: Probing cell-division phenotype space and Polo-like kinase function using small molecules.

Journal: Nature chemical biology 20061101

Title: Polo-like kinase (Plk) 1 as a target for prostate cancer management.

Journal: IUBMB life 20051001

Title: Xu F, et al. Rigosertib as a selective anti-tumor agent can ameliorate multiple dysregulated signalingtransduction pathways in high-grade myelodysplastic syndrome. Sci Rep. 2014 Dec 4;4:7310.

Title: Hyoda T, et al. Rigosertib induces cell death of a myelodysplastic syndrome-derived cell line by DNA damage-induced G2/M arrest. Cancer Sci. 2015 Mar;106(3):287-93.

Title: Gumireddy K, et al. ON01910, a non-ATP-competitive small molecule inhibitor of Plk1, is a potent anticancer agent. Cancer Cell. 2005 Mar;7(3):275-86.

Title: Reddy MV, et al. Discovery of a clinical stage multi-kinase inhibitor sodium (E)-2-{2-methoxy-5-[(2',4',6'-trimethoxystyrylsulfonyl)methylphenylamino}acetate (ON 01910.Na): synthesis, structure-activity relationship, and biological activity. J Med Chem. 2011 Sep 22;54(18):6254-76.

Title: Chapman CM, et al. ON 01910.Na is selectively cytotoxic for chronic lymphocytic leukemia cells through a dual mechanism of action involving PI3K/AKT inhibition and induction of oxidative stress. Clin Cancer Res. 2012 Apr 1;18(7):1979-91

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