111339-51-6

Basic information

• Product Name: 3-methyl-2-quinoxalinyl phenyl sulfide
• Synonyms: 3-methyl-2-quinoxalinyl phenyl sulfide
• CAS NO: 111339-51-6
• Molecular Formula: C₁₅H₁₂N₂S
• Molecular Weight: 252.33418
• Mol File: 111339-51-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-methyl-2-quinoxalinyl phenyl sulfide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-2-quinoxalinyl phenyl sulfide(111339-51-6)
• EPA Substance Registry System: 3-methyl-2-quinoxalinyl phenyl sulfide(111339-51-6)

Safety Data

• Hazardous Substances Data: 111339-51-6(Hazardous Substances Data)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 32601-86-8 2-chloro-3-methylquinoxaline 
• 108-98-5 thiophenol 

Downstream Products

• 111339-59-4 3-Phenylthiochinoxalin-2-carbaldehydtosylhydrazon 
• 111339-53-8 C₂₃H₂₀N₄OS 
• 111339-66-3 4-Phenylthio-1,2,3-triazolo<1,5-a>chinoxalin 
• 92822-95-2 3-Phenylthiochinoxalin-2-carbaldehyd 
• 366018-67-9 2-Benzenesulfonyl-3-[(E)-2-(4-fluoro-phenyl)-vinyl]-quinoxaline 
• 366018-68-0 2-Benzenesulfonyl-3-[(E)-2-(2-chloro-phenyl)-vinyl]-quinoxaline 
• 366018-66-8 2-phenylsulphonyl-3-styrylquinoxaline 
• 60638-86-0 2-methyl-3-phenylsulphonylquinoxaline 
• 111339-52-7 1-(3-Phenylsulfanyl-quinoxalin-2-ylmethyl)-pyridinium; iodide 

Relevant articles and documents

Antiplasmodial 2-thiophenoxy-3-trichloromethyl quinoxalines target the apicoplast of Plasmodium falciparum

The identification of a plant-like Achille's Heel relict, i.e. the apicoplast, that is essential for Plasmodium spp., the causative agent of malaria lead to an attractive drug target for new antimalarials with original mechanism of action. Although it is not photosynthetic, the apicoplast retains several anabolic pathways that are indispensable for the parasite. Based on previously identified antiplasmodial hit-molecules belonging to the 2-trichloromethylquinazoline and 3-trichloromethylquinoxaline series, we report herein an antiplasmodial Structure-Activity Relationships (SAR) study at position two of the quinoxaline ring of 16 newly synthesized compounds. Evaluation of their activity toward the multi-resistant K1 Plasmodium falciparum strain and cytotoxicity on the human hepatocyte HepG2 cell line revealed a hit compound (3k) with a PfK1 EC50 value of 0.3 μM and a HepG2 CC50 value of 56.0 μM (selectivity index = 175). Moreover, hit-compound 3k was not cytotoxic on VERO or CHO cell lines and was not genotoxic in the in vitro comet assay. Activity cliffs were observed when the trichloromethyl group was replaced by CH3, CF3 or H, showing that this group played a key role in the antiplasmodial activity. Biological investigations performed to determine the target and mechanism of action of the compound 3k strongly suggest that the apicoplast is the putative target as showed by severe alteration of apicoplaste biogenesis and delayed death response. Considering that there are very few molecules that affect the Plasmodium apicoplast, our work provides, for the first time, evidence of the biological target of trichloromethylated derivatives.