7409-21-4

Upstream product

• 108-24-7 acetic anhydride 
• 1008-79-3 1-phenyl-1H-pyrazol-3-ol 

Downstream Products

• 7189-05-1 1-(1,3-diphenyl-1H-pyrazol-4-yl)ethan-1-one 
• 7409-28-1 1-(3-hydroxy-1-phenyl-1H-pyrazol-4-yl)ethan-1-one 
• 1354413-67-4 4-methyl-2,6-diphenyl-2H-pyrazolo[4,3-c]pyridine 
• 1354413-65-2 1-{1-phenyl-3-[(E)-2-phenylethenyl]-1H-pyrazol-4-yl}ethanone 
• 1354413-64-1 tert-butyl (2E)-3-(4-acetyl-1-phenyl-1H-pyrazol-3-yl)acrylate 
• 1354413-63-0 ethyl (2E)-3-(4-acetyl-1-phenyl-1H-pyrazol-3-yl)acrylate 
• 1354413-59-4 1-[1-phenyl-3-(2-phenylethynyl)-1H-pyrazol-4-yl]ethanone 
• 1354413-57-2 1-[3-(2-naphthyl)-1-phenyl-1H-pyrazol-4-yl]ethanone 
• 1354413-56-1 1-[1-phenyl-3-(3-thienyl)-1H-pyrazol-4-yl]ethanone 
• 1354413-55-0 1-{3-[4-(trifluoromethyl)phenyl-1-phenyl-]-1H-pyrazol-4-yl}ethanone 
• 1354413-54-9 1-[3-(3-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]ethanone 
• 1354413-52-7 4-acetyl-1-phenyl-1H-pyrazol-3-yl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Synthesis and anti-mitotic activity of 2,4- or 2,6-disubstituted- and 2,4,6-trisubstituted-2H-pyrazolo[4,3-c]pyridines

An efficient synthetic route for the synthesis of 2H-pyrazolo[4,3-c]pyridines, primarily varying by the substituents at the 2-, 4- and 6-positions, is described here. A Sonogashira-type cross-coupling reaction was employed to yield 3-alkynyl-1H-pyrazole-4-carbaldehydes, ethanones and propanones from the corresponding 1H-pyrazol-3-yl trifluoromethanesulfonates. Subsequent treatment of the coupling products with dry ammonia afforded a versatile library of 2H-pyrazolo[4,3-c]pyridines, which were then evaluated for their cytotoxicity against K562 and MCF-7 cancer cell lines. The most potent of these compounds displayed low micromolar GI50 values in both cell lines. Active compounds induced dose-dependent cell-cycle arrest in mitosis, as shown by flow cytometric analysis of DNA content and phosphorylation of histone H3 at serine-10. Moreover, biochemical assays revealed increased activities of caspases-3/7 in treated cells, specific fragmentation of PARP-1, and phosphorylation of Bcl-2, collectively confirming apoptosis as the mechanism of cell death.

Synthesis of 3-substituted 1-phenyl-1H-pyrazole-4-carbaldehydes and the corresponding ethanones by Pd-catalysed cross-coupling reactions

An efficient synthetic route to construct ortho-substituted 1-phenyl-1H-pyrazole-4-carboxaldehydes and the corresponding ethanones starting from 1-phenyl-1H-pyrazol-3-ol is described. Carbon-carbon bond-forming Pd-catalysed cross-coupling reactions were applied for the functionalisation of the intermediate pyrazole triflates. Detailed NMR spectroscopic investigations were undertaken with all obtained products. ARKAT-USA, Inc.