544675-64-1

Basic information

• Product Name: Pyrimidine, 4-ethynyl-2-(methylthio)- (9CI)
• Synonyms: Pyrimidine, 4-ethynyl-2-(methylthio)- (9CI);4-ethynyl-2-(methylthio)pyrimidine
• CAS NO: 544675-64-1
• Molecular Formula: C₇H₆N₂S
• Molecular Weight: 150.20094
• Product Categories: PYRIMIDINE
• Mol File: 544675-64-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyrimidine, 4-ethynyl-2-(methylthio)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimidine, 4-ethynyl-2-(methylthio)- (9CI)(544675-64-1)
• EPA Substance Registry System: Pyrimidine, 4-ethynyl-2-(methylthio)- (9CI)(544675-64-1)

Safety Data

• Hazardous Substances Data: 544675-64-1(Hazardous Substances Data)

Upstream product

• 544675-63-0 2-methylsulfanyl-4-trimethylsilanylethynyl-pyrimidine 
• 49844-90-8 4-Chloro-2-methylthiopyrimidine 
• 1122-74-3 4-iodo-2-(methylthio)pyrimidine 
• 1066-54-2 trimethylsilylacetylene 

Relevant articles and documents

Structure–Activity Relationships of 2-Sufonylpyrimidines as Quorum-Sensing Inhibitors to Tackle Biofilm Formation and eDNA Release of Pseudomonas aeruginosa

Drug-resistant Pseudomonas aeruginosa (PA) strains are on the rise, making treatment with current antibiotics ineffective. Hence, circumventing resistance or restoring the activity of antibiotics by novel approaches is of high demand. Targeting the Pseudomonas quinolone signal quorum sensing (PQS-QS) system is an intriguing strategy to abolish PA pathogenicity without affecting the viability of the pathogen. Herein we report the structure–activity relationships of 2-sulfonylpyrimidines, which were previously identified as dual-target inhibitors of the PQS receptor PqsR and the PQS synthase PqsD. The SAR elucidation was guided by a combined approach using ligand efficiency and ligand lipophilicity efficiency to select the most promising compounds. In addition, the most effective inhibitors were rationally modified by the guidance of QSAR using Hansch analyses. Finally, these inhibitors showed the capacity to decrease biofilm mass and extracellular DNA, which are important determinants for antibiotic resistance.

PYRAZOLYL-PYRIMIDINE DERIVATIVES AS KINASE INHIBITORS

The present invention relates to pyrazolyl-pyrimidine derivatives which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing such compounds or the pharmaceutical compositions containing them.

PYRAZOLYL-PYRIMIDINE DERIVATIVES AS KINASE INHIBITORS

The present invention relates to pyrazolyl-pyrimidine derivatives which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing such compounds or the pharmaceutical compositions containing them.

CHEMICAL COMPOUNDS

The present invention discloses pyrimidine derivatives, compositions and medicaments containing the same, as well as processes for the preparation and use of such compounds, compositions and medicaments. Such pyrimidine derivatives are useful in the treat

N-phenyl-4-pyrazolo[1,5-6]pyridazin-3-ylpyrimidin-2-amines as potent and selective inhibitors of glycogen synthase kinase 3 with good cellular efficacy

Glycogen synthase kinase 3 regulates glycogen synthase, the rate-determining enzyme for glycogen synthesis. Liver and muscle glycogen synthesis is defective in type 2 diabetics, resulting in elevated plasma glucose levels. Inhibition of GSK-3 could potentially be an effective method to control plasma glucose levels in type 2 diabetics. Structure-activity studies on a N-phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine series have led to the identification of potent and selective compounds with good cellular efficacy. Molecular modeling studies have given insights into the mode of binding of these inhibitors. Since the initial leads were also potent inhibitors of CDK-2/CDK-4, an extensive SAR was performed at various positions of the pyrazolo[1,5-b] pyridazin core to afford potent GSK-3 inhibitors that were highly selective over CDK-2. In addition, these inhibitors also exhibited very good cell efficacy and functional response. A representative example was shown to have good oral exposure levels, extending their utility in an in vivo setting. These inhibitors provide a viable lead series in the discovery of new therapies for the treatment of type 2 diabetes.

PYRADAZINE COMPOUNDS AS GSK-3 INHIBITORS

The present invention relates generally to inhibitors of the kinases, such as GSK3, and more particularly to fused pyradazine compounds according to formula (I) and methods of their use.