83824-38-8

Basic information

• Product Name: 1-Methyl-1,4-dihydro-pyrazolo[4,3-d]pyrimidine-5,7-dione
• Synonyms: 1-Methyl-1,4-dihydro-pyrazolo[4,3-d]pyrimidine-5,7-dione;1-METHYL-1H-PYRAZOLO[4,3-D]PYRIMIDINE-5,7-DIOL
• CAS NO: 83824-38-8
• Molecular Formula: C₆H₆N₄O₂
• Molecular Weight: 166.13744
• Mol File: 83824-38-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-Methyl-1,4-dihydro-pyrazolo[4,3-d]pyrimidine-5,7-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-1,4-dihydro-pyrazolo[4,3-d]pyrimidine-5,7-dione(83824-38-8)
• EPA Substance Registry System: 1-Methyl-1,4-dihydro-pyrazolo[4,3-d]pyrimidine-5,7-dione(83824-38-8)

Safety Data

• Hazardous Substances Data: 83824-38-8(Hazardous Substances Data)

Usage

Molecular structure

1-Methyl-1,4-dihydro-pyrazolo[4,3-d]pyrimidine-5,7-dione has a complex molecular structure with a pyrazolopyrimidine core and a methyl group attached to the first carbon.

Class of organic compounds

It belongs to the pyrazolopyrimidine class of organic compounds.

Mechanism of action

Febuxostat is a xanthine oxidase inhibitor that works by reducing the production of uric acid in the body.

Medical use

It is used for the treatment of gout and hyperuricemia, preventing the formation of urate crystals in the joints and kidneys.

Prescription status

Febuxostat is a prescription medication and should be used under the guidance of a healthcare professional.

Side effects and interactions

It has potential side effects and interactions that should be monitored by a healthcare professional. (Listed in the material provided)

Upstream product

• 92534-73-1 4-amino-1-methyl-1H-pyrazole-5-carboxamide 
• 92534-72-0 1-methyl-4-nitro-1H-pyrazole-5-carboxamide 
• 309740-49-6 methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1006962-20-4 1-methyl-4-nitro-1H-pyrazole-5-carbonyl chloride 
• 92534-69-5 1-methyl-4-nitro-1H-pyrazole-5-carboxylic acid 
• 923283-54-9 methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate 
• 57-13-6 urea 
• 16034-46-1 1-methyl-1H-pyrazole-5-carboxylic acid 
• 939979-31-4 C₅H₈N₄O*ClH 

Downstream Products

• 939979-32-5 5,7-dichloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine 
• 1285500-09-5 (S)-1-ethyl-3-(4-(1-methyl-7-(3-methylmorpholino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)urea 
• 1357086-75-9 5-{[(4-methoxy-phenyl)carbamoyl]amino}-8-(furan-2-yl)-1-methyl-1H-pyrazolo[3,4-e][1,2,4]triazolo[1,5-c]pyrimidine 
• 1357086-88-4 5-cyclohexylamino-8-(furan-2-yl)-1-methyl-1H-pyrazolo[3,4-e][1,2,4]triazolo[1,5-c]pyrimidine 
• 1357086-91-9 8-(furan-2-yl)-1-methyl-5-(4-phenylpiperazin-1-yl)-1H-pyrazolo[3,4-e][1,2,4]triazolo[1,5-c]pyrimidine 
• 1285500-13-1 (S)-1-ethyl-3-(4-(7-(3-ethylmorpholino)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)urea 
• 1285500-14-2 1-(4-(7-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-methyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-ethylurea 

Relevant articles and documents

Novel pyrazolo[4,3-d]pyrimidine microtubule targeting agents (MTAs): Synthesis, structure–activity relationship, in vitro and in vivo evaluation as antitumor agents

The design, synthesis, and biological evaluation of a series novel N1?methyl pyrazolo[4,3-d]pyrimidines as inhibitors of tubulin polymerization and colchicine binding were described here. Synthesis of target compounds involved alkylation of the pyrazolo scaffold, which afforded two regioisomers. These were separated, characterized and identified with 1H NMR and NOESY spectroscopy. All compounds, except 10, inhibited [3H]colchicine binding to tubulin, and the potent inhibition was similar to that obtained with CA-4. Compounds 9 and 11–13 strongly inhibited the polymerization of tubulin, with IC50 values of 0.45, 0.42, 0.49 and 0.42 μM, respectively. Compounds 14–16 inhibited the polymerization of tubulin with IC50s near ～1 μM. Compounds 9, 12, 13 and 16 inhibited MCF-7 breast cancer cell lines and circumvented βIII-tubulin mediated cancer cell resistance to taxanes and other MTAs, and compounds 9–17 circumvented Pgp-mediated drug resistance. In the standard NCI testing protocol, compound 9 exhibited excellent potency with low to sub nanomolar GI50 values (≤10 nM) against most tumor cell lines, including several multidrug resistant phenotypes. Compound 9 was significantly (P 0.0001) better than paclitaxel at reducing MCF-7 TUBB3 (βIII-tubulin overexpressing) tumors in a mouse xenograft model. Collectively, these studies support the further preclinical development of the pyrazolo[4,3-d]pyrimidine scaffold as a new generation of tubulin inhibitors and 9 as an anticancer agent with advantages over paclitaxel.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

A hit to lead discovery of novel N-methylated imidazolo-, pyrrolo-, and pyrazolo-pyrimidines as potent and selective mTOR inhibitors

A series of N-7-methyl-imidazolopyrimidine inhibitors of the mTOR kinase have been designed and prepared, based on the hypothesis that the N-7-methyl substituent on imidazolopyrimidine would impart selectivity for mTOR over the related PI3Kα and δ kinases. The corresponding N-Me substituted pyrrolo[3,2-d]pyrimidines and pyrazolo[4,3-d]pyrimidines also show potent mTOR inhibition with selectivity toward both PI3α and δ kinases. The most potent compound synthesized is pyrazolo[4,3-d]pyrimidine 21c. Compound 21c shows a Ki of 2 nM against mTOR inhibition, remarkable selectivity (>2900×) over PI3 kinases, and excellent potency in cell-based assays.