62004-35-7

Usage

Uses

Used in Pharmaceutical Industry:
LFM-A13 is used as an anti-leukemic agent for targeting Bruton's tyrosine kinase (BTK) in the treatment of leukemia. By inhibiting BTK, LFM-A13 can potentially help in controlling the growth and progression of leukemia cells, offering a new therapeutic approach for patients suffering from this disease.

Biological Activity

Potent and selective inhibitor of Bruton's tyrosine kinase (BTK). Inhibits recombinant BTK with an IC 50 value of 2.5 μ M and has no activity on other protein kinases ( including JAK1, JAK3, HCK, EGFR kinase and insulin receptor kinase) at concentrations of up to 278 μ M.

InChI:InChI=1/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-

Upstream product

• 63034-99-1 N-(2,5-dibromophenyl)-2-cyanoacetamide 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 3638-73-1 2,5-dibromoaniline 

Relevant academic research and scientific papers

ATP competitive inhibitors of d-alanine-d-alanine ligase based on protein kinase inhibitor scaffolds

d-Alanine-d-alanine ligase (DDl) is an essential enzyme in bacterial cell wall biosynthesis and an important target for developing new antibiotics. Here, we describe a new approach to identify new inhibitor scaffolds for DDl based on similarity in the ATP

Large-scale synthesis of GMP grade α-cyano-β-hydroxy-β- methyl-N-(2,5-dibromophenyl) propenamide (LFM-A13), a new anti-cancer drug candidate

The leflunomide (CAS 75706-12-6) metabolite (LFM) analog α-cyano-β-hydroxy-β-methyl-N-(2,5-dibromophenyl)-propenamide (LFM-A13, DDE-28, CAS 244240-24-2), is a rationally designed inhibitor of the anti-apoptotic enzyme Bruton's tyrosine kinase (BTK). LFM-A

Structural influence on the intermolecular/intramolecular hydrogen bonding in solid state of substituted leflunomides: Evidence by X-ray crystal structure

We report the results of an X-ray crystal structure study of nine substituted leflunomide metabolite analogs (LFM). Comparison of the hydrogen bonding characteristics exhibited by these structurally distinct LFM analogs was especially informative about the inter- and intra-molecular hydrogen bonding patterns that exist in the crystal structure of individual compounds. All compounds had the strong intramolecular hydrogen bonds. In addition, with the exception of the 2,5-difluorophenyl substituted LFM analog, all other compounds formed inter- or intra-molecular hydrogen bonds with the halogen atom and the NH group. However, we found that the presence of a fluorine atom at the 2-position on the phenyl ring of the 2,5-difluoro and 2-fluoro derivatives resulted in only one intramolecular hydrogen bond in the structural framework. Conversely, the 3,5-difluoro substituted LFM analog had an intramolecular hydrogen bond common to the other halide substituted derivatives. The anomaly exhibited by the 2,5-difluoro and the 2-fluoro substituted compounds may be owing to the smaller size of fluorine atom in comparison with the chlorine and bromine atoms in the structures of the other analogs. The presence of a fluorine at the 2-position of the phenyl ring may disrupt the intermolecular hydrogen bonding that was observed for the other derivatives due to differences in the crystal packing for these molecules.

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

The specific inhibitor of the protein tyrosine kinase, Bruton's tyrosine kinase (BTK), α-cyano-β-hydroxy-β-methyl-N-(2,5-dibromophenyl)- propenamide (LFM-A13, CAS 244240-24-2), is a chemosensitizing antileukemic agent with antithrombotic properties. Oral

Inhibitors of the EGF-receptor tyrosine kinase and methods for their use

Novel compounds and pharmaceutical compositions useful as EGFR tyrosine kinase inhibitors. Methods of the invention include administration of the EGFR TK inhibitors to treat diseases characterized by enhanced expression of EGF, including cancers, particularly breast cancer. Additionally, a homology model representing the structure of EGFR kinase domain is provided, which model is useful for the rationally design and screening of compounds predicted to bind favorably to EGFR and to inhibit EGFR TK.

BTK inhibitors and methods for their identification and use

The invention provides BTK inhibitors, methods for their identification and use, and pharmaceutical compositions comprising BTK inhibitors.

α-Cyano-N-(2,5-dibromophenyl)-β-hydroxybut-2-enamide

The title compound, C11H8Br2N2O2 (LFM-A13), is the first reported BTK-specific tyrosine kinase inhibitor and the first antileukemic agent targeting BTK (Bruton's tyrosine kinase). The crystal structur