35252-96-1

Usage

Uses

Used in Pharmaceutical Industry:
6-(Chloromethyl)-2-methylpyrimidin-4-ol is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structural features, including the chloromethyl and methyl groups, as well as the hydroxyl group, make it a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 6-(Chloromethyl)-2-methylpyrimidin-4-ol serves as a valuable research tool for studying the structure-activity relationships of pyrimidine-based compounds. Its presence in various chemical libraries allows scientists to investigate its interactions with biological targets and evaluate its potential as a lead compound for drug discovery.

InChI:InChI=1/C6H7ClN2O/c1-4-8-5(3-7)2-6(10)9-4/h2H,3H2,1H3,(H,8,9,10)

Upstream product

• 638-07-3 ethyl (2-chloroaceto)acetate 
• 124-42-5 acetamidine hydrochloride 
• 68087-21-8 4-diethylaminomethyl-2-methyl-6-hydroxy-pyrimidine 
• 109-89-7 diethylamine 

Relevant academic research and scientific papers

Structural optimization of aminopyrimidine-based CXCR4 antagonists

Structural optimization of aminopyrimidine-based CXCR4 antagonists is reported. The optimization is guided by molecular docking studies based on available CXCR4-small molecule crystal complex. The optimization identifies a number of compounds with improved receptor binding affinity and functional activity exemplified by compound 23 (inhibition of APC-conjugate clone 12G5 for CXCR4 binding in a cell based assay: IC50 = 8.8 nM; inhibition of CXCL12 induced cytosolic calcium increase: IC50 = 0.02 nM). In addition, compound 23 potently inhibits CXCR4/CXLC12 mediated chemotaxis in a matrigel invasion assay. Furthermore, compound 23 exhibits good physicochemical properties (MW 367, clogP 2.1, PSA 48, pKa 7.2) and in vitro safety profiles (marginal/moderate inhibition of CYP isozymes and hERG). These results represent significant improvement over the initial hit from scaffold hybridization and suggest that compound 23 can be used as a starting point to support lead optimization.

Design, synthesis, and evaluation of novel CXCR4 antagonists based on an aminoquinoline template

The chemokine receptor CXCR4 has been explored as a drug target due to its involvement in pathological conditions such as HIV infection and cancer metastasis. Here we report the structure–activity relationship study of novel CXCR4 antagonists based on an aminoquinoline template. This template is devoid of the chiral center in the classical tetrahydroquinoline (THQ) ring moiety and therefore can be easily synthesized. A number of potent CXCR4 antagonists were identified, exemplified by compound 3, which demonstrated excellent binding affinity with CXCR4 receptor (IC50 = 57 nM) and inhibited CXCL12 induced cytosolic calcium increase (IC50 = 0.24 nM). Furthermore, compound 3 potently inhibited CXLC12/CXCR4 mediated cell migration in a transwell invasion assay. The simplified synthetic approach combined with good physicochemical properties (e.g. MW 362, clogP 2.1, PSA 48, pKa 7.0 for compound 3) demonstrate the potential of this aminoquinoline template as a novel scaffold to develop CXCR4 antagonists.

HETEROARYL COMPOUNDS AS CXCR4 INHIBITORS, COMPOSITION AND METHOD USING THE SAME

The present disclosure provides heteroaryl compounds of Formula (I), processes for their preparation, pharmaceutical compositions containing them, and their use in the treatment of diseases and disorders, arising from or related to the CXCR4 pathway.

Combating pests with 4-substituted-pyrimidin-6-yl (thiono)-phosphoric (phosphonic) acid esters or ester amides

4-Substituted-pyrimidin-6-yl (thiono)-phosphoric (phosphonic) acid esters or ester-amides of the formula STR1 in which R represents hydrogen, alkyl, alkoxy, alkylthio or alkylamino, R1 represents halogen, alkoxy, alkylthio or alkylamino, R2 represents alkyl, alkoxy, alkylamino or phenyl, R3 represents alkyl and X and Y, which may be identical or different, represent oxygen or sulphur, Which possess arthropodicidal and nematicidal properties.