32275-63-1

Usage

Type of compound

Heterocyclic compound

Structural features

Contains an indazole and carboxylic acid group, with a phenyl substituent attached to the tetrahydroindazole ring

Potential pharmacological and medicinal properties

Of interest for drug discovery and development

Uses in organic synthesis

Building block for the preparation of more complex molecules

Additional research needed

To fully understand its potential properties and applications

Upstream product

• 123345-90-4 4,5,6,7-tetrahydro-1-phenyl-1-H-indazole-3-carbaldehyde 
• 5396-14-5 ethyl 2-oxo-2-(2-oxocyclohexyl)acetate 
• 100-63-0 phenylhydrazine 
• 18841-76-4 D-galactose phenylhydrazone 
• 93019-39-7 1-phenyl-4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid ethyl ester 
• 2562-37-0 1-nitrocyclohexene 

Downstream Products

• 14714-06-8 1-phenyl-4,5,6,7-tetrahydro-1H-indazole 

Relevant academic research and scientific papers

Pyrazole-4-Carboxamide (YW2065): A Therapeutic Candidate for Colorectal Cancer via Dual Activities of Wnt/β-Catenin Signaling Inhibition and AMP-Activated Protein Kinase (AMPK) Activation

Dysregulation of the Wnt/β-catenin signaling pathway has been widely recognized as a pathogenic mechanism for colorectal cancer (CRC). Although numerous Wnt inhibitors have been developed, they commonly suffer from toxicity and unintended effects. Moreover, concerns have been raised in targeting this pathway because of its critical roles in maintaining stem cells and regenerating tissues and organs. On the basis of the anthelmintic drug pyrvinium and previous lead FX1128, we have developed a compound YW2065 (1c) which demonstrated excellent anti-CRC effects in vitro and in vivo. YW2065 achieves its inhibitory activity for Wnt signaling by stabilizing Axin-1, a scaffolding protein that regulates proteasome degradation of β-catenin. Simultaneously, YW2065 also led to the activation of the tumor suppressor AMPK, providing an additional anticancer mechanism. In addition, YW2065 showed favorable pharmacokinetic properties without obvious toxicity. The anti-CRC effect of YW2065 was highlighted by its promising efficacy in a mice xenograft model.

REACTION OF D-GALACTOSE PHENYLHYDRAZONE WITH NITROALKENES:SYNTHESIS OF PENTAHYDROXYPENTYLPYRAZOLES

D-Galactose phenylhydrazone reacts with 1- and 2-substituted and 1,2-disubstituted nitroalkenes, with loss of the nitro group, to give moderate yields of 3-(D-galacto-pentitol-1-yl)-1-phenylpyrazoles variously substituted at positins 4, 5 and a mechanism is proposed.Acetylation of these products affords pentaacetates and periodate oxidation gave the corresponding 1-phenylpyrazole-3-carbaldehyde derivatives, some of which were oxidised to the carboxylic acids.U.v., i.r., and n.m.r. data confirm the proposed structures.