5848-05-5

Usage

Uses

Used in Pharmaceutical Drug Development:
4-(4-Fluorophenyl)-1H-pyrazol-5-amine is used as a building block in the development of potential pharmaceutical drugs for the treatment of various diseases, including cancer, inflammation, and neurological disorders. Its unique structure and properties contribute to the design and synthesis of novel drug candidates with improved therapeutic effects.
Used in Medicinal Chemistry Research:
4-(4-Fluorophenyl)-1H-pyrazol-5-amine is used as a valuable tool in medicinal chemistry research to explore its full potential in the field. Further studies and investigations are ongoing to understand its interactions with biological targets and to optimize its properties for specific therapeutic applications.

InChI:InChI=1/C23H15N3O3/c1-13-2-6-19-20(8-13)26-22(25-19)15(11-24)10-17-4-7-21(29-17)14-3-5-18-16(9-14)12-28-23(18)27/h2-10H,12H2,1H3,(H,25,26)/b15-10+

Upstream product

• 459-22-3 4-fluorophenylacetonitrile 
• 320416-88-4 C₁₁H₁₁FN₂ 
• 398-42-5 2-formyl-2-(4-fluorophenyl) acetonitrile 

Downstream Products

• 77493-82-4 3-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-05-7 3-(4-fluorophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-12-6 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1404447-04-6 3-(4-fluorophenyl)-5-(pyridin-3-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1609188-71-7 3β-hydroxy-5'-methyl-3'-(p-fluorophenyl)-5-en-androst[17,16-g]pyrazolo[1,5-a]pyrimidine 
• 1448466-65-6 8-(4-fluorophenyl)-2-thioxo-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one 
• 1306753-76-3 ethyl 4-(2-dimethylaminovinyl)-8-(4-fluorophenyl)pyrazolo[5,1-c][1,2,4]triazin-3-carboxylate 
• 1030476-76-6 C₁₃H₁₀FN₃O 
• 919745-15-6 C₁₃H₉ClFN₃ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel pyrazolo[1,5-a]pyrimidines: Discovery of a selective inhibitor of JAK1 JH2 pseudokinase and VPS34

A series of novel 3,6-di-substituted or 3-substituted pyrazolo[1,5-a]pyrimidines were prepared via a microwave-assisted approach that generated a broad array of derivatives in good yields (20–93%, ave. = 59%). The straightforward synthesis involved sequential treatment of commercially-available acetonitrile derivatives with DMF-dimethylacetal (120 °C, 20 min), followed by treatment with NH2NH2·HBr (120 °C, 20 min), and 1,1,3,3-tetramethoxypropane or 2-aryl-substituted malondialdehdyes (120 °C, 20 min). Compounds were screened for antimitotic activities against MCF7 breast cancer and/or A2780 ovarian cancer cell lines in vitro. The most active compounds exhibited EC50 values ranging from 0.5 to 4.3 μM, with the 3-(4-(trifluoromethyl)phenyl)-6-[4-(2-(piperidin-1-yl)ethoxy]phenyl analogue (34e) and the 3-(2-fluorophenyl)-6-[4-(2-(4-methylpiperizin-1-yl)ethoxy]phenyl analogue (35a) being two to three fold more active than Compound C (Dorsomorphin) in A2780 and MCF7 assays, respectively. Importantly, a monosubstituted 3-(benzothiazol-2-yl) derivative (13) was equipotent with the more synthetically challenging 3,6-disubstituted derivatives (34a–e and 35a–e), and exhibited a promising and unique selectivity profile when screened against a panel consisting of 403 protein kinases (Kinomescan selectivity score = 0.005, Kd = 0.55 ± 0.055 μM and 0.410 ± 0.20 μM for JAK1 JH2 pseudokinase and VPS34, respectively).

A new, one-pot, multicomponent synthesis of 5-aza-9-deaza-adenines under microwave irradiation

A new, practical, three-component method for the synthesis of 5-aza-9-deaza-adenines is developed. Aminopyrazoles react in a one-pot fashion with triethyl orthoformate and cyanamide under microwave irradiation affording 5-aza-9-deaza-adenines in good yiel

Discovery and characterization of a novel 7-aminopyrazolo[1,5-a]pyrimidine analog as a potent hepatitis C virus inhibitor

We describe a novel 7-aminopyrazolo[1,5-a]pyrimidine (7-APP) derivative as a potent hepatitis C virus (HCV) inhibitor. A series of 7-APPs was synthesized and evaluated for inhibitory activity against HCV in different cell culture systems. The synthesis and preliminary structure-activity relationship study of 7-APP are reported.