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244240-24-2,MFCD09878279
Catalog No.:AA00BE7Q

244240-24-2 | LFM-A13

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5mg
≥98%
in stock  
$98.00   $68.00
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10mg
in stock  
$183.00   $128.00
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25mg
≥97%
in stock  
$432.00   $303.00
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50mg
in stock  
$558.00   $390.00
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200mg
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$1,308.00   $915.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BE7Q
Chemical Name:
LFM-A13
CAS Number:
244240-24-2
Molecular Formula:
C11H8Br2N2O2
Molecular Weight:
360.0014
MDL Number:
MFCD09878279
SMILES:
C/C(=C(/C(=N/c1cc(Br)ccc1Br)/O)\C#N)/O
Properties
Computed Properties
 
Complexity:
386  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
3.8  

Downstream Synthesis Route

[1]Ghosh,Sutapa;Uckun,FatihM.[ActaCrystallographica,SectionC:CrystalStructureCommunications,1999,vol.55,#8,p.1364-1365]

[2]Tibbles,HeatherE.;Samuel,Peter;Erbeck,Doug;Mahajan,Sandeep;Uckun,FatihM.[Arzneimittel-Forschung/DrugResearch,2004,vol.54,#6,p.330-339]

[3]Venkatachalam;Zheng;Ghosh;Uckun[JournalofMolecularStructure,2005,vol.743,#1-3,p.103-115]

[1]DuMez,Darin;Venkatachalam,TaracadK.;Uckun,FatihM.[Arzneimittel-Forschung/DrugResearch,2007,vol.57,#3,p.155-163]

[1]DuMez,Darin;Venkatachalam,TaracadK.;Uckun,FatihM.[Arzneimittel-Forschung/DrugResearch,2007,vol.57,#3,p.155-163]

[2]Venkatachalam;Zheng;Ghosh;Uckun[JournalofMolecularStructure,2005,vol.743,#1-3,p.103-115]

[3]Tibbles,HeatherE.;Samuel,Peter;Erbeck,Doug;Mahajan,Sandeep;Uckun,FatihM.[Arzneimittel-Forschung/DrugResearch,2004,vol.54,#6,p.330-339]

[4]Ghosh,Sutapa;Uckun,FatihM.[ActaCrystallographica,SectionC:CrystalStructureCommunications,1999,vol.55,#8,p.1364-1365]

Literature

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: Bruton's tyrosine kinase inhibitors: approaches to potent and selective inhibition, preclinical and clinical evaluation for inflammatory diseases and B cell malignancies.

Journal: Journal of medicinal chemistry 20120524

Title: Suppression of Etk/Bmx protects against ischemic brain injury.

Journal: Cell transplantation 20120101

Title: Toll-like receptor 4-, 7-, and 8-activated myeloid cells from patients with X-linked agammaglobulinemia produce enhanced inflammatory cytokines.

Journal: The Journal of allergy and clinical immunology 20120101

Title: Essential role of Stat3 in PI3K-induced oncogenic transformation.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20110809

Title: Bruton's tyrosine kinase is required for TLR-dependent heme oxygenase-1 gene activation via Nrf2 in macrophages.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20110715

Title: In vitro and in vivo chemosensitizing activity of LFM-A13, a dual-function inhibitor of Bruton's tyrosine kinase and polo-like kinases, against human leukemic B-cell precursors.

Journal: Arzneimittel-Forschung 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Tec protein tyrosine kinase inhibits CD25 expression in human T-lymphocyte.

Journal: Immunology letters 20100104

Title: ATP competitive inhibitors of D-alanine-D-alanine ligase based on protein kinase inhibitor scaffolds.

Journal: Bioorganic & medicinal chemistry 20090201

Title: Tec kinases regulate actin assembly and cytokine expression in LPS-stimulated human neutrophils via JNK activation.

Journal: Cellular immunology 20090101

Title: Discovery of new inhibitors of D-alanine:D-alanine ligase by structure-based virtual screening.

Journal: Journal of medicinal chemistry 20081211

Title: Bone marrow X kinase-mediated signal transduction in irradiated vascular endothelium.

Journal: Cancer research 20080415

Title: Role of different protein tyrosine kinases in fMLP-induced neutrophil transmigration.

Journal: Immunobiology 20080101

Title: A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20071218

Title: Chemosensitizing anti-cancer activity of LFM-A13, a leflunomide metabolite analog targeting polo-like kinases.

Journal: Cell cycle (Georgetown, Tex.) 20071215

Title: Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets.

Journal: Journal of medicinal chemistry 20070809

Title: Anti-breast cancer activity of LFM-A13, a potent inhibitor of Polo-like kinase (PLK).

Journal: Bioorganic & medicinal chemistry 20070115

Title: Preclinical toxicity and pharmacokinetics of the Bruton's tyrosine kinase-targeting anti-leukemic drug candidate, alpha-cyano-beta-hydroxy-beta-methyl-N- (2,5-dibromophenyl) propenamide (LFM-A13).

Journal: Arzneimittel-Forschung 20070101

Title: Large-scale synthesis of GMP grade alpha-cyano-beta-hydroxy-beta-methyl-N-(2,5-dibromophenyl) propenamide (LFM-A13), a new anti-cancer drug candidate.

Journal: Arzneimittel-Forschung 20070101

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Roles for phosphoinositide 3-kinases, Bruton's tyrosine kinase, and Jun kinases in B lymphocyte chemotaxis and homing.

Journal: European journal of immunology 20060501

Title: Signaling through CD16b in human neutrophils involves the Tec family of tyrosine kinases.

Journal: Journal of leukocyte biology 20050801

Title: Dual targeting of Bruton's tyrosine kinase and Janus kinase 3 with rationally designed inhibitors prevents graft-versus-host disease (GVHD) in a murine allogeneic bone marrow transplantation model.

Journal: British journal of haematology 20040901

Title: The Btk inhibitor LFM-A13 is a potent inhibitor of Jak2 kinase activity.

Journal: Biological chemistry 20040501

Title: In vivo toxicity and antithrombotic profile of the oral formulation of the antileukemic agent, LFM-A13-F.

Journal: Arzneimittel-Forschung 20040101

Title: The anti-leukemic Bruton's tyrosine kinase inhibitor alpha-cyano-beta-hydroxy-beta-methyl-N-(2,5-dibromophenyl) propenamide (LFM-A13) prevents fatal thromboembolism.

Journal: Leukemia & lymphoma 20030901

Title: Chemotactic factor-induced recruitment and activation of Tec family kinases in human neutrophils. II. Effects of LFM-A13, a specific Btk inhibitor.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20030515

Title: BCR targets cyclin D2 via Btk and the p85alpha subunit of PI3-K to induce cell cycle progression in primary mouse B cells.

Journal: Oncogene 20030417

Title: Inhibition of host kinase activity altered by the LMP2A signalosome-a therapeutic target for Epstein-Barr virus latency and associated disease.

Journal: Antiviral research 20021201

Title: Silencing of Bruton's tyrosine kinase (Btk) using short interfering RNA duplexes (siRNA).

Journal: FEBS letters 20020911

Title: In vivo pharmacokinetic features, toxicity profile, and chemosensitizing activity of alpha-cyano-beta-hydroxy-beta- methyl-N-(2,5-dibromophenyl)propenamide (LFM-A13), a novel antileukemic agent targeting Bruton's tyrosine kinase.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20020501

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Tyrosine kinase inhibitors against EGF receptor-positive malignancies.

Journal: Methods in molecular biology (Clifton, N.J.) 20010101

Title: Rational design and synthesis of a novel anti-leukemic agent targeting Bruton's tyrosine kinase (BTK), LFM-A13 [alpha-cyano-beta-hydroxy-beta-methyl-N-(2, 5-dibromophenyl)propenamide].

Journal: The Journal of biological chemistry 19990402

Title: Mahajan S, et al. Rational design and synthesis of a novel anti-leukemic agent targeting Bruton's tyrosine kinase (BTK), LFM-A13 [alpha-cyano-beta-hydroxy-beta-methyl-N-(2, 5-dibromophenyl)propenamide J Biol Chem. 1999 Apr 2;274(14):9587-99.

Title: van den Akker E, et al. The Btk inhibitor LFM-A13 is a potent inhibitor of Jak2 kinase activity. Biol Chem. 2004 May;385(5):409-13.

Title: "Sahin K, et al. LFM-A13, a potent inhibitor of polo-like kinase, inhibits breast carcinogenesis by suppressing proliferation activity and inducing apoptosis in breast tumors of mice. Invest New Drugs. 2017 Nov 15."

Title: Uckun FM, et al. Anti-breast cancer activity of LFM-A13, a potent inhibitor of Polo-like kinase (PLK). Bioorg Med Chem. 2007 Jan 15;15(2):800-14. Epub 2006 Oct 26.

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