29274-22-4

Basic information

• Product Name: 5-Hydroxypyrazolo[1,5-a]pyrimidine
• Synonyms: 5-Hydroxypyrazolo[1,5-a]pyrimidine;Pyrazolo[1,5-a]pyrimidin-5-ol;4H,5H-pyrazolo[1,5-a]pyriMidin-5-one;1H-pyrazolo[1,5-a]pyrimidin-5-one;pyrazolo[1,5-a]pyrimidin-5(4H)-one(WXC06578)
• CAS NO: 29274-22-4
• Molecular Formula: C₆H₅N₃O
• Molecular Weight: 135.126
• Mol File: 29274-22-4.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 243.174°C at 760 mmHg
• Flash Point: 100.868°C
• Appearance: /
• Density: 1.511g/cm³
• Vapor Pressure: 0.033mmHg at 25°C
• Refractive Index: 1.739
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-Hydroxypyrazolo[1,5-a]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxypyrazolo[1,5-a]pyrimidine(29274-22-4)
• EPA Substance Registry System: 5-Hydroxypyrazolo[1,5-a]pyrimidine(29274-22-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 29274-22-4(Hazardous Substances Data)

Usage

General Description

5-Hydroxypyrazolo[1,5-a]pyrimidine is a chemical compound with the molecular formula C4H4N4O. It is a heterocyclic compound containing a pyrazolopyrimidine core structure. 5-Hydroxypyrazolo[1,5-a]pyrimidine has been identified as an inhibitor of the enzyme cyclic GMP-specific phosphodiesterase type 5 (PDE5), which is involved in the regulation of blood flow in the body. Inhibiting PDE5 can lead to vasodilation and increased blood flow, making it useful in the treatment of erectile dysfunction. Due to its pharmaceutical potential, 5-Hydroxypyrazolo[1,5-a]pyrimidine has been studied for its therapeutic applications and is a key component in the development of erectile dysfunction medications like Viagra.

InChI:InChI=1/C6H5N3O/c10-6-2-4-9-5(8-6)1-3-7-9/h1-4H,(H,8,10)

Upstream product

• 874-14-6 1,3-dimethyluracil 
• 1225387-53-0 3⁽⁵⁾-aminopyrazole 
• 1001-26-9 ethyl 3-ethoxyacrylate 
• 922-67-8 propynoic acid methyl ester 
• 1224944-43-7 sodium pyrazolo[1,5-a] pyrimidin-5-olate 
• 1820-80-0 3-aminopyrazole 
• 623-47-2 propynoic acid ethyl ester 
• 89464-32-4 prop-2-ynylcarbamic acid ethyl ester 
• 105-37-3 Ethyl propionate 
• 5941-55-9 ethyl 3-ethoxyacrylate 

Downstream Products

• 29274-25-7 4-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one 
• 29274-24-6 5-chloropyrazolo[1,5-a]pyrimidine 
• 1224944-45-9 methyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 1224944-48-2 5-chloro-N-cyclohexylpyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-62-0 5-chloro-N-(3-(5-chloro-2-methylphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224942-00-0 5-amino-N-(3-(5-chloro-2-methylphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-49-3 5-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-72-2 5-chloro-N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224942-05-5 N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)-5-(cyclopropylmethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224939-88-1 5-amino-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-51-7 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester 
• 1224939-90-5 methyl 5-(3-fluorobenzylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 1224944-68-6 5-chloro-N-(3-(2,5-dimethylphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-67-5 5-chloro-N-(3-(2,5-dimethylphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 

Relevant articles and documents

Design, synthesis and biological evaluation of macrocyclic derivatives as TRK inhibitors

Tropomyosin receptor kinases (TRKA, TRKB, TRKC) are transmembrane receptor tyrosine kinases, which are respectively encoded by NTRK1, NTRK2, and NTRK3 genes. Herein, we reported the design, synthesis and Structure-Activity Relationship (SAR) investigation of a series of macrocyclic derivatives as new TRK inhibitors. Among these compounds, compound 9e exhibited strong kinase inhibitory activity (TRKG595R IC50 = 13.1 nM) and significant antiproliferative activity in the Ba/F3-LMNA-NTRK1 cell line (IC50 = 0.080 μM) and compound 9e has shown a better inhibitory effect (IC50 = 0.646 μM) than control drug LOXO-101 in Ba/F3-LMNA-NTRK1-G595R cell line. These results indicate that compound 9e is a potential TRK inhibitor for further investigation.

Optimization of pyrazolo[1,5-a]pyrimidines lead to the identification of a highly selective casein kinase 2 inhibitor

Casein kinase 2 (CK2) is a constitutively expressed serine/threonine kinase that has a large diversity of cellular substrates. Thus, CK2 has been associated with a plethora of regulatory functions and dysregulation of CK2 has been linked to disease development in particular to cancer. The broad implications in disease pathology makes CK2 an attractive target. To date, the most advanced CK2 inhibitor is silmitasertib, which has been investigated in clinical trials for treatment of various cancers, albeit several off-targets for silmitasertib have been described. To ascertain the role of CK2 inhibition in cancer, other disease and normal physiology the development of a selective CK2 inhibitor would be highly desirable. In this study we explored the pyrazolo [1,5-a]pyrimidine hinge-binding moiety for the development of selective CK2 inhibitors. Optimization of this scaffold, which included macrocyclization, led to IC20 (31) a compound that displayed high in vitro potency for CK2 (KD = 12 nM) and exclusive selectivity for CK2. X-ray analysis revealed a canonical type-I binding mode for IC20 (31). However, the polar carboxylic acid moiety that is shared by many CK2 inhibitors including silmitasertib was required for potency but limits the cellular activity of IC20 (31) and the cellular IC50 dropped to the low micromolar range. In summary, IC20 (31) represents a highly selective and potent inhibitor of CK2, which can be used as a tool compound to study CK2 biology and potential new applications for the treatment of diseases.

COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.