85544-41-8

Usage

General Description

2,4-Pyrimidinediamine, 5-((4-ethoxy-3-methoxyphenyl)methyl)-, also known as EML4-ALK inhibitor, is a chemical compound used in the development of targeted therapies for certain types of cancer. It functions as an inhibitor of the EML4-ALK fusion protein, which is frequently found in non-small cell lung cancer. By blocking this protein, the compound can potentially stop the growth and spread of cancer cells. Research on 2,4-Pyrimidinediamine, 5-((4-ethoxy-3-methoxyphenyl)methyl)- is ongoing, and it shows promise as a potential treatment for certain cancers.

InChI:InChI=1/C14H18N4O2/c1-3-20-11-5-4-9(7-12(11)19-2)6-10-8-17-14(16)18-13(10)15/h4-5,7-8H,3,6H2,1-2H3,(H4,15,16,17,18)

Upstream product

• 656810-50-3 (Z)-2-(4-Ethoxy-3-methoxy-benzyl)-3-morpholin-4-yl-acrylonitrile 
• 120-25-2 4-ethoxy-3-methoxybenzaldehyde 
• 113-00-8 guanidine nitrate 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 85544-55-4 5-(2-Bromo-4-ethoxy-5-methoxy-benzyl)-pyrimidine-2,4-diamine 

Relevant academic research and scientific papers

Target Guided Synthesis of 5-Benzyl-2,4-diamonopyrimidines: Their Antimalarial Activities and Binding Affinities to Wild Type and Mutant Dihydrofolate Reductases from Plasmodium falciparum

The resistance to pyrimethamine (PYR) of Plasmodium falciparum arising from mutation at position 108 of dihydrofolate reductase (pfDHFR) from serine to asparagine (S108N) is due to steric interaction between the bulky side chain of N108 and C1 atom of the 5-p-C1 aryl group of PYR, which consequently resulted in the reduction in binding affinity between the enzyme and inhibitor. Molecular modeling suggested that the flexible antifolate, such as trimethoprim (TMP) derivatives, could avoid this steric constraint and should be considered as new, potentially effective compounds. The hydrophobic interaction between the side chain of inhibitor and the active site of the enzyme around position 108 was enhanced by the introduction of a longer and more hydrophobic side chain on TMP's 5-benzyl moiety. The prepared compounds, especially those bearing aromatic substituents, exhibited better binding affinities to both wild type and mutant enzymes than the parent compound. Binding affinities of these compounds correlated well with their antimalarial activities against both wild type and resistant parasites. Molecular modeling of the binding of such compounds with pfDHFR also supported the experimental data and clearly showed that aromatic substituents play an important role in enhancing binding affinity. In addition, some compounds with 6-alkyl substituents showed relatively less decrease in binding constants with the mutant enzymes and relatively good antimalarial activities against the parasites bearing the mutant enzymes.

Pharmaceutical compositions

The compounds of the general Formula I STR1 (wherein R1 and R2 may be the same or different and each stands for hydrogen, hydroxy, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C2-6 alkenyloxy or p

Synthesis and antimycobacterial effects of some lipophilic substituted 2,4-diamino-5-benzylpyrimidines

2,4-Diamino-5-benzylpyrimidines 1-23 with lipophilic substitution in the benzylic moiety were synthesized by the morpholino-anilino-procedure. Their effects against various mycobacteria were verified by MIC (minimum inhibitory concentration) in whole cells and I50-measurements in whole cell and cell-free systems. Especially the substances 7-12 are strong inhibitors of some atypical mycobacterial strains which are sometimes associated with tuberculosis in the elderly and with AIDS. They might be promising candidates for therapy.