307322-32-3

Basic information

• Product Name: 5-Naphthalen-2-yl-2H-pyrazole-3-carboxylic acid hydrazide
• Synonyms: 5-Naphthalen-2-yl-2H-pyrazole-3-carboxylic acid hydrazide
• CAS NO: 307322-32-3
• Molecular Formula: C14H12N4O
• Molecular Weight: 252.27128
• Mol File: 307322-32-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Naphthalen-2-yl-2H-pyrazole-3-carboxylic acid hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Naphthalen-2-yl-2H-pyrazole-3-carboxylic acid hydrazide(307322-32-3)
• EPA Substance Registry System: 5-Naphthalen-2-yl-2H-pyrazole-3-carboxylic acid hydrazide(307322-32-3)

Safety Data

• Hazardous Substances Data: 307322-32-3(Hazardous Substances Data)

Upstream product

• 144252-18-6 4-naphthalen-2-yl-2,4-dioxo-butyric acid methyl ester 
• 93-08-3 methyl 2-naphthyl ketone 
• 164295-93-6 methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate 
• 1245919-39-4 5-naphthalen-2-yl-1H-pyrazole-3-carbonyl chloride 
• 164295-94-7 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylic acid 

Downstream Products

• 1245919-41-8 SKI-I-Asp 
• 1285498-45-4 C₂₀H₁₅N₅O 

Relevant articles and documents

Design, synthesis and analysis of novel sphingosine kinase-1 inhibitors to improve oral bioavailability

The sphingomyelin pathway is important in cell regulation and determining cellular fate. Inhibition of sphingosine kinase isoform 1 (SK1) within this pathway, leads to a buildup of sphingosine and ceramide, two molecules directly linked to cell apoptosis, while decreasing the intracellular concentration of sphingosine-1-phosphate (S1P), a molecule linked to cellular proliferation. Recently, an inhibitor capable of inhibiting SK1 in vitro was identified, but also shown to be ineffective in vivo. A set of compounds designed to assess the impact of synthetic modifications to the hydroxynaphthalene ring region of the template inhibitor with SK1 to obtain a compound with increased efficacy in vivo. Of these fifteen compounds, 4A was shown to have an IC50 = 6.55 μM with improved solubility and in vivo potential.

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.