464185-13-5

Upstream product

• 1008-79-3 1-phenyl-1H-pyrazol-3-ol 
• 7409-31-6 4-bromo-3-hydroxy-1-phenyl-1H-pyrazole 
• 1354413-50-5 3-(benzyloxy)-1-phenyl-1H-pyrazol 
• 100-44-7 benzyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 1354413-49-2 3-(benzyloxy)-4-bromo-1-phenyl-1H-pyrazole 
• 88585-10-8 ethyl 3-hydroxy-1-phenyl-1H-pyrazole-4-carboxylate 

Downstream Products

• 888741-36-4 ethyl 3-(3-hydroxy-1-phenyl-1H-pyrazol-4-yl)propanoate 
• 1354413-53-8 3-[4-(trifluoromethyl)phenyl]-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 1273924-72-3 1-phenyl-3-(thiophen-3-yl)-1H-pyrazole-4-carboxaldehyde 
• 1354413-58-3 1-phenyl-3-(2-phenylethynyl)-1H-pyrazole-4-carbaldehyde 
• 1354413-60-7 ethyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate 
• 1354413-61-8 tert-butyl (2E)-3-(4-formyl-1-phenyl-1H-pyrazol-3-yl)acrylate 
• 1354413-62-9 1-phenyl-3-[(E)-2-phenylethenyl]-1H-pyrazole-4-carbaldehyde 
• 1354413-66-3 2,6-diphenyl-2H-pyrazolo[4,3-c]pyridine 
• 1354413-51-6 4-formyl-1-phenyl-1H-pyrazol-3-yl trifluoromethanesulfonate 
• 21487-45-6 1,3-diphenyl-4-formylpyrazole 
• 36640-43-4 3-(3-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 36640-53-6 3-(naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 32828-75-4 2-phenyl-2H-pyrazolo[4,3-c]pyridine 

Relevant academic research and scientific papers

Synthesis of N-aryl-2,6-diphenyl-2H-pyrazolo[4,3-c]pyridin-7-amines and their photodynamic properties in the human skin melanoma cell line G361

A small series of N-aryl-2,6-diphenyl-2H-pyrazolo[4,3-c]pyridin-7-amines was synthesized from easily accessible 1-phenyl-1H-pyrazol-3-ol via 7-iodo-2,6-diphenyl-2H-pyrazolo[4,3-c]pyridine and 7-iodo-4-methyl-2,6-diphenyl-2H-pyrazolo[4,3-c]pyridine intermediates and their subsequent use in palladium catalyzed Buchwald-Hartwig cross-coupling reaction with various anilines. Majority of the compounds were not significantly cytotoxic to melanoma G361 cells in the dark up to 10 μM concentration, but their activity could be increased by irradiation with visible blue light (414 nm). The most active compound 10 possessed EC50 values of 3.5, 1.6 and 0.9 μM in cells irradiated with 1, 5 and 10 J/cm2, respectively. The treatment caused generation of reactive oxygen species in cells and extensive DNA damage, documented by the comet assay and by detection of phosphorylated histone H2A.X, followed by apoptotic cell death. Our results suggest that N-aryl-2,6-diphenyl-2H-pyrazolo[4,3-c]pyridin-7-amines could serve as a potential source of photosensitizing compounds with anticancer activities.

Synthesis and antiproliferative activity of 2,4,6,7-tetrasubstituted-2h-pyrazolo[4,3-c]pyridines

A library of 2,4,6,7-tetrasubstituted-2H-pyrazolo[4,3-c]pyridines was prepared from easily accessible 1-phenyl-3-(2-phenylethynyl)-1H-pyrazole-4-carbaldehyde via an iodine-mediated elec-trophilic cyclization of intermediate 4-(azidomethyl)-1-phenyl-3-(phenylethynyl)-1H-pyrazoles to 7-iodo-2,6-diphenyl-2H-pyrazolo[4,3-c]pyridines followed by Suzuki cross-couplings with various boronic acids and alkylation reactions. The compounds were evaluated for their antiproliferative activity against K562, MV4-11, and MCF-7 cancer cell lines. The most potent compounds displayed low micromolar GI50 values. 4-(2,6-Diphenyl-2H-pyrazolo[4,3-c]pyridin-7-yl)phenol proved to be the most active, induced poly(ADP-ribose) polymerase 1 (PARP-1) cleavage, activated the initiator enzyme of apoptotic cascade caspase 9, induced a fragmentation of microtubule-associated protein 1-light chain 3 (LC3), and reduced the expression levels of proliferating cell nuclear antigen (PCNA). The obtained results suggest a complex action of 4-(2,6-diphenyl-2H-pyrazolo[4,3-c]pyridin-7-yl)phenol that combines antiproliferative effects with the induction of cell death. Moreover, investigations of the fluorescence properties of the final compounds revealed 7-(4-methoxyphenyl)-2,6-diphenyl-2H-pyrazolo[4,3-c]pyridine as the most potent pH indicator that enables both fluorescence intensity-based and ratiometric pH sensing.

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.

FIVE-MEMBERED HETEROCYCLIC ALKANOIC ACID DERIVATIVE

The present invention relates to a compound represented by the formula wherein R1 is an optionally substituted 5-membered heterocyclic group; X is a bond etc.; Q is a divalent hydrocarbon group having 1 to 20 carbon atoms; Y is a bond etc.; rin

1,2-AZOLE DERIVATIVES WITH HYPOGLYCEMIC AND HYPOLIPIDEMIC ACTIVITY

A compound represented by the formula (1) wherein ring A is a ring optionally having 1 to 3 substituents; ring B is a 1,2-azole ring which may further have 1 to 3 substituents; Xa, Xb and Xc are the same or different and each is a bond, - O -, - S - and the like; Ya is a divalent aliphatic hydrocarbon residue having 1 to 20 carbon atoms; Yb and Yc are the same or different and each is a bond or a divalent aliphatic hydrocarbon residue having 1 to 20 carbon atoms; ring C is a monocyclic aromatic ring which may further have 1 to 3 substituents; and R represents -OR4 (R4 is hydrogen atom or optionally substituted hydrocarbon group) and the like, or a salt thereof or a prodrug thereof is useful as an agent for the prophylaxis or treatment of diabetes and the like.