890006-82-3

Usage

Uses

Used in Pharmaceutical Research and Development:
3-(4-FLUOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID is used as a starting compound for the development of new drugs or lead compounds due to its potential biological activity and suitability for further chemical modifications. Its unique structure allows researchers to explore its therapeutic potential across a range of medical conditions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-(4-FLUOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID serves as a key intermediate for the synthesis of other biologically active molecules. The presence of the carboxylic acid group facilitates its incorporation into more complex molecular frameworks, potentially leading to the discovery of novel therapeutic agents.
Used in Drug Design and Optimization:
3-(4-FLUOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID is utilized as a structural component in drug design and optimization processes. Its ability to be modified and functionalized allows for the fine-tuning of its properties to enhance its therapeutic efficacy, selectivity, and pharmacokinetic profile, ultimately contributing to the creation of more effective medications.

Upstream product

• 64393-83-5 4-(4-fluorophenyl)-2,4-dioxobutanoic acid 
• 462-06-6 fluorobenzene 
• 192701-91-0 methyl 5-(4-fluorophenyl)-1H-pyrazole-3-carboxylate 
• 39757-34-1 methyl 4-(4-fluorophenyl)-2,4-diketobutyrate 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Downstream Products

• 1188373-00-3 5-(4-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide 
• 1232027-99-4 5-(4-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide 
• 866588-11-6 ethyl 5-(4-fluorophenyl)-1H-pyrazole-3-carboxylate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel hydroxamic acid based histone deacetylase 6 selective inhibitors bearing phenylpyrazol scaffold as surface recognition motif

In recent years, inhibition of HDAC6 became a promising therapeutic strategy for the treatment of cancer and HDAC6 inhibitors were considered to be potent anti-cancer agents. In this work, celecoxib showed moderate degree of HDAC6 inhibition activity and selectivity in preliminary enzyme inhibition activity assay. A series of hydroxamic acid derivatives bearing phenylpyrazol moiety were designed and synthesized as HDAC6 inhibitors. Most compounds showed potent HDAC6 inhibition activity. 11i was the most selective compound against HDAC6 with IC50 values of 0.020 μM and selective factor of 101.1. Structure-activity relationship analysis indicated that locating the linker group at 1′ of pyrazol gave the most selectivity. The most compounds 11i (GI50 = 3.63 μM) exhibited 6-fold more potent than vorinostat in HepG2 cells. Considering of the high selectivity against HDAC6 and anti-proliferation activity, such compounds have potential to be developed as anti-cancer agents.

5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII

Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 μM). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho- and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 μM. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors.

Synthesis and anticancer activity of heteroaromatic linked 4β-amido podophyllotoxins as apoptotic inducing agents

A series of different heteroaromatic linked 4β-amidopodophyllotoxin conjugates (16a-i, 17a-i and 18a-d) were synthesized and evaluated for anticancer activity against five human cancer cell lines. Among the series, one of the compound 17g showed significant antiproliferative activity in A549 (lung cancer) cell line. Flow cytometric analysis showed that 17g arrested the cell cycle in the G2/M phase leading to caspase-3 dependent apoptotic cell death. Further, Hoechst 33258 staining and DNA fragmentation assay also suggests that 17g induces cell death by apoptosis.

NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-COA DESATURASE

The present invention relates to piperazine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE

The present invention relates to piperidine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.