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LFM-A13

CAS No.:
244240-24-2
Catalog Number:
AG00BEAI
Molecular Formula:
C11H8Br2N2O2
Molecular Weight:
360.0014
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$140
- +
10mg
99%
1 week
United States
$190
- +
50mg
99%
1 week
United States
$587
- +
Product Description
Catalog Number:
AG00BEAI
Chemical Name:
LFM-A13
CAS Number:
244240-24-2
Molecular Formula:
C11H8Br2N2O2
Molecular Weight:
360.0014
MDL Number:
MFCD09878279
IUPAC Name:
(Z)-2-cyano-N-(2,5-dibromophenyl)-3-hydroxybut-2-enamide
InChI:
InChI=1S/C11H8Br2N2O2/c1-6(16)8(5-14)11(17)15-10-4-7(12)2-3-9(10)13/h2-4,16H,1H3,(H,15,17)/b8-6-
InChI Key:
UVSVTDVJQAJIFG-VURMDHGXSA-N
SMILES:
C/C(=C(/C(=N/c1cc(Br)ccc1Br)/O)\C#N)/O
Properties
Complexity:
386  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
359.893g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
360.005g/mol
Monoisotopic Mass:
357.895g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
73.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.8  
Literature
Title Journal
Dissecting the phenotypes of Plk1 inhibition in cancer cells using novel kinase inhibitory chemical CBB2001. Laboratory investigation; a journal of technical methods and pathology 20121001
Bruton's tyrosine kinase inhibitors: approaches to potent and selective inhibition, preclinical and clinical evaluation for inflammatory diseases and B cell malignancies. Journal of medicinal chemistry 20120524
Suppression of Etk/Bmx protects against ischemic brain injury. Cell transplantation 20120101
Toll-like receptor 4-, 7-, and 8-activated myeloid cells from patients with X-linked agammaglobulinemia produce enhanced inflammatory cytokines. The Journal of allergy and clinical immunology 20120101
Essential role of Stat3 in PI3K-induced oncogenic transformation. Proceedings of the National Academy of Sciences of the United States of America 20110809
Bruton's tyrosine kinase is required for TLR-dependent heme oxygenase-1 gene activation via Nrf2 in macrophages. Journal of immunology (Baltimore, Md. : 1950) 20110715
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. Arzneimittel-Forschung 20110101
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
Tec protein tyrosine kinase inhibits CD25 expression in human T-lymphocyte. Immunology letters 20100104
ATP competitive inhibitors of D-alanine-D-alanine ligase based on protein kinase inhibitor scaffolds. Bioorganic & medicinal chemistry 20090201
Tec kinases regulate actin assembly and cytokine expression in LPS-stimulated human neutrophils via JNK activation. Cellular immunology 20090101
Discovery of new inhibitors of D-alanine:D-alanine ligase by structure-based virtual screening. Journal of medicinal chemistry 20081211
Bone marrow X kinase-mediated signal transduction in irradiated vascular endothelium. Cancer research 20080415
Role of different protein tyrosine kinases in fMLP-induced neutrophil transmigration. Immunobiology 20080101
A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases. Proceedings of the National Academy of Sciences of the United States of America 20071218
Chemosensitizing anti-cancer activity of LFM-A13, a leflunomide metabolite analog targeting polo-like kinases. Cell cycle (Georgetown, Tex.) 20071215
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets. Journal of medicinal chemistry 20070809
Anti-breast cancer activity of LFM-A13, a potent inhibitor of Polo-like kinase (PLK). Bioorganic & medicinal chemistry 20070115
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). Arzneimittel-Forschung 20070101
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. Arzneimittel-Forschung 20070101
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Roles for phosphoinositide 3-kinases, Bruton's tyrosine kinase, and Jun kinases in B lymphocyte chemotaxis and homing. European journal of immunology 20060501
Signaling through CD16b in human neutrophils involves the Tec family of tyrosine kinases. Journal of leukocyte biology 20050801
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. British journal of haematology 20040901
The Btk inhibitor LFM-A13 is a potent inhibitor of Jak2 kinase activity. Biological chemistry 20040501
In vivo toxicity and antithrombotic profile of the oral formulation of the antileukemic agent, LFM-A13-F. Arzneimittel-Forschung 20040101
The anti-leukemic Bruton's tyrosine kinase inhibitor alpha-cyano-beta-hydroxy-beta-methyl-N-(2,5-dibromophenyl) propenamide (LFM-A13) prevents fatal thromboembolism. Leukemia & lymphoma 20030901
Chemotactic factor-induced recruitment and activation of Tec family kinases in human neutrophils. II. Effects of LFM-A13, a specific Btk inhibitor. Journal of immunology (Baltimore, Md. : 1950) 20030515
BCR targets cyclin D2 via Btk and the p85alpha subunit of PI3-K to induce cell cycle progression in primary mouse B cells. Oncogene 20030417
Inhibition of host kinase activity altered by the LMP2A signalosome-a therapeutic target for Epstein-Barr virus latency and associated disease. Antiviral research 20021201
Silencing of Bruton's tyrosine kinase (Btk) using short interfering RNA duplexes (siRNA). FEBS letters 20020911
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. Clinical cancer research : an official journal of the American Association for Cancer Research 20020501
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
Tyrosine kinase inhibitors against EGF receptor-positive malignancies. Methods in molecular biology (Clifton, N.J.) 20010101
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]. The Journal of biological chemistry 19990402
Properties