164295-94-7

Usage

Uses

Used in Pharmaceutical Industry:
5-NAPHTHALEN-2-YL-1H-PYRAZOLE-3-CARBOXYLIC ACID is used as a building block for the synthesis of various bioactive compounds due to its versatile reactivity and potential pharmacological properties.
Used in Research Applications:
5-NAPHTHALEN-2-YL-1H-PYRAZOLE-3-CARBOXYLIC ACID is used as a reference standard in analytical chemistry for its unique molecular structure and potential to contribute to the development of new drugs and therapies.
Used in Anti-inflammatory Applications:
5-NAPHTHALEN-2-YL-1H-PYRAZOLE-3-CARBOXYLIC ACID is studied for its anti-inflammatory properties, which may contribute to the development of treatments for various inflammatory conditions.
Used in Antimicrobial Applications:
5-NAPHTHALEN-2-YL-1H-PYRAZOLE-3-CARBOXYLIC ACID is studied for its antimicrobial activities, which may lead to the development of new antibiotics or antimicrobial agents.
Used in Anticancer Applications:
5-NAPHTHALEN-2-YL-1H-PYRAZOLE-3-CARBOXYLIC ACID is studied for its potential anticancer activities, which may contribute to the development of new cancer treatments or therapies.

InChI:InChI=1/C14H10N2O2/c17-14(18)13-8-12(15-16-13)11-6-5-9-3-1-2-4-10(9)7-11/h1-8H,(H,15,16)(H,17,18)

Upstream product

• 164295-82-3 2-hydroxy-4-naphthalen-2-yl-4-oxo-but-2-enoic acid 
• 144252-18-6 4-naphthalen-2-yl-2,4-dioxo-butyric acid methyl ester 
• 105356-61-4 4-(naphthalen-2-yl)-2,4-dioxobutanoic acid 
• 91-20-3 naphthalene 
• 93-08-3 methyl 2-naphthyl ketone 
• 164295-93-6 methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate 

Downstream Products

• 307322-32-3 5-naphthalen-2-yl-1H-pyrazol-3-carboxylic acid hydrazide 

Relevant academic research and scientific papers

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 bioactivity of sphingosine kinase inhibitors and their novel aspirinyl conjugated analogs

Sphingosine kinase (SphK) is a lipid kinase with oncogenic activity, and SphK inhibitors (SKIs) are known for their anti-cancer activity. Here, we report highly efficient syntheses of SKIs and their aspirinyl (Asp) analogs. Both SKIs and their Asp analogs were highly cytotoxic towards multiple human cancer cell lines; in several cases the Asp analogs were up to three times more effective. Furthermore, they were equally potent inhibitors of SphK. The pharmacokinetic study indicated that SKI-I-Asp cleaved efficiently to form SKI-I and the half-life of SKI-I was increased from ～7 h in SKI-I to ～10 h in SKI-I-Asp injected mice, thereby prolonging its effect. In summary, the Asp-conjugated SKIs seem to be promising prodrugs of SKIs where delivery in vivo remains a problem.

SPHINGOSINE KINASE INHIBITORS

The invention relates to compounds, compositions and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, autoimmune disease, inflammatory disease, or allergy.