21314-17-0

Usage

Uses

Used in Organic Synthesis:
4-HYDROXY-1-PHENYLPYRAZOLO[3,4-D]PYRIMIDINE is used as a synthetic building block for the creation of various complex organic molecules. Its chemical properties allow it to be a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-HYDROXY-1-PHENYLPYRAZOLO[3,4-D]PYRIMIDINE is used as a key intermediate in the development of novel drugs. Its unique structure can be exploited to design and synthesize new therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Agrochemical Industry:
4-HYDROXY-1-PHENYLPYRAZOLO[3,4-D]PYRIMIDINE is also utilized in the agrochemical industry as a starting material for the synthesis of new pesticides, herbicides, and other crop protection agents. Its incorporation into these products can lead to the development of more effective and environmentally friendly solutions for agricultural challenges.
Used in Research and Development:
In the realm of research and development, 4-HYDROXY-1-PHENYLPYRAZOLO[3,4-D]PYRIMIDINE serves as an important compound for exploring new chemical reactions and understanding the underlying mechanisms. Its use in this context can contribute to the advancement of scientific knowledge and the discovery of innovative applications in various fields.

InChI:InChI=1/C11H8N4O/c16-11-9-6-14-15(10(9)12-7-13-11)8-4-2-1-3-5-8/h1-7H,(H,12,13,16)

Upstream product

• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 123-06-8 Ethoxymethylenemalononitrile 
• 532-55-8 Benzoyl isothiocyanate 
• 109-94-4 formic acid ethyl ester 
• 5334-30-5 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 100-66-3 methoxybenzene 
• 108-90-7 chlorobenzene 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 78972-83-5 1-Phenyl-5-<(dimethylamino)methylenamino>-4-pyrazolcarbonitril 
• 76164-73-3 Ethyl 3-(4-Carbamoyl-2-phenyl-3-pyrazoloamino)methylene-2,4-dioxovalerate 
• 141-53-7 sodium formate 
• 77287-34-4 formamide 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 

Downstream Products

• 92556-20-2 dimethyl-[2-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-ethyl]-amine 
• 1197864-10-0 1-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-ol 
• 393845-82-4 4-(4-(4-fluorophenyl)piperazin-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 393820-30-9 8-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane 
• 313225-41-1 4-(4-cyclohexylpiperazin-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 393845-64-2 1-phenyl-4-[(4-phenylpiperazin)-1-yl]-1H-pyrazolo[3,4-d]pyrimidine 
• 313518-74-0 1-phenyl-4-(4-(pyridin-2-yl)piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine 
• 612038-12-7 4-(4-(4-fluorobenzyl)piperazin-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 305337-65-9 4-(4-(4-chlorophenyl)piperazin-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 305337-66-0 1-phenyl-4-(4-(p-tolyl)piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine 
• 393845-87-9 4-(4-(4-nitrophenyl)piperazin-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 393846-02-1 4-(4-(4-methoxyphenyl)piperazin-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 

Relevant academic research and scientific papers

Design, synthesis, and anticancer screening for repurposed pyrazolo[3,4-d]pyrimidine derivatives on four mammalian cancer cell lines

The present study reports the synthesis of new purine bioisosteres comprising a pyra-zolo[3,4-d]pyrimidine scaffold linked to mono-, di-, and trimethoxy benzylidene moieties through hydrazine linkages. First, in silico docking experiments of the synthesized compounds against Bax, Bcl-2, Caspase-3, Ki67, p21, and p53 were performed in a trial to rationalize the observed cytotoxic activity for the tested compounds. The anticancer activity of these compounds was evaluated in vitro against Caco-2, A549, HT1080, and Hela cell lines. Results revealed that two (5 and 7) of the three synthesized compounds (5, 6, and 7) showed high cytotoxic activity against all tested cell lines with IC50 values in the micro molar concentration. Our in vitro results show that there is no significant apoptotic effect for the treatment with the experimental compounds on the viability of cells against A549 cells. Ki67 expression was found to decrease significantly following the treatment of cells with the most promising candidate: drug 7. The overall results indicate that these pyrazolopy-rimidine derivatives possess anticancer activity at varying doses. The suggested mechanism of action involves the inhibition of the proliferation of cancer cells.

Synthesis, evaluation and docking of novel pyrazolo pyrimidines as potent p38α MAP kinase inhibitors with improved anti-inflammatory, ulcerogenic and TNF-α inhibitory properties

A series of nine new N-substituted-4-((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)benzamides (6a-i) derivatives was synthesized. All the compounds were screened in-vitro for BSA anti-denaturation property, antioxidant assay and p38α MAP kinase inhibition. The in vitro anti-inflammatory assay results revealed that the compounds (6f-i) showed better activity than the compounds 6a-e. Compound 6f bearing the 4-chlorophenyl group showed in vitro anti-inflammatory activity (82.35 ± 4.04) comparable to standard drug diclofenac sodium (84.13 ± 1.63) and better p38α MAP kinase inhibitory activity (IC50 = 0.032 ± 1.63 μM) than the prototypic inhibitor SB203580 (IC50 = 0.041 ± 1.75 μM). The selected active compounds (6f-i) were further studied in animal models for anti-inflammatory activity, ulcerogenic liability, lipid peroxidation and TNF-α inhibition potential. Compound 6f showed promising anti-inflammatory potential with a percentage inhibition of 83.73% when compared to the standard, diclofenac sodium (78.05%). Compound 6f was also found to show reduced ulcerogenic liability and lipid peroxidation in comparison to the standard. This compound also potently inhibited the lipopolysaccharide (LPS)-induced TNF-α production in mice model (ID50 = 8.23 mg/kg) in comparison to SB 203580 (ID50 = 26.38 mg/kg). The molecular docking of compounds 6a-i against p38α MAP kinase receptor was also performed to understand ligand receptor interaction. Amongst all synthesized molecules compound 6f displayed highest docking score of ?9.824. It showed hydrogen bonding interactions with Asn115 and pi-cation interaction with Lys53.

Synthesis of pyrazolo[3,4-d]pyrimidin-4(5H)-ones tethered to 1,2,3-triazoles and their evaluation as potential anticancer agents

A series of hybrid aza heterocycles containing pyrazolo[3,4-d]pyrimidin-4(5H)-ones tethered to 1,2,3-triazole scaffold were synthesized from 1,3-dipolar cycloaddition reaction of pyrazolopyrimidinone based alkyne with azides using Cu(II) catalyst in presence of sodium ascorbate and evaluated for their anticancer efficacy in vitro against C6 rat and U87 human glioma cell lines. These compounds induced a concentration dependent inhibition of C6 rat and U87 human glioma cell proliferation. Compound 5f arrested the cells at S-phase of the cell cycle and induced apoptosis in U87 GBM cell lines. Further, apoptosis was evidenced by the cleavage of Caspase-3, PARP and up regulation of p53. In silico docking studies reveal that the compounds 5a, 5f and 5l were more effective in binding with TGFBR2 than other compounds.

ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF

Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

Ultrasonic-Assisted Synthesis of Pyrazolo[3,4-d]pyrimidin-4-ol Tethered with 1,2,3-Triazoles and Their Anticancer Activity

Abstract: In the presents work synthesis and characterization of new heterocyclic derivatives containing pyrazolo[3,4-d]pyrimidine linkage with 1,4-disubstituted-1,2,3-triazoles via methylene-oxy group. The selected synthesized compounds were tested for their in-vitro anticancer activity against various cancer cell lines. Synthesis of compounds was done under ultrasonic-assisted Huisgen 1,3-dipolar cycloaddition reaction with good yields. Some of the newly synthesized compounds demonstrated good to moderate anticancer activity, most of compounds shows activity against renal cancer cell lines.

New pyrazolopyrimidine derivatives as Leishmania amazonensis arginase inhibitors

Arginase performs the first enzymatic step in polyamine biosynthesis in Leishmania and represents a promising target for drug development. Polyamines in Leishmania are involved in trypanothione synthesis, which neutralize the oxidative burst of reactive oxygen species (ROS) and nitric oxide (NO) that are produced by host macrophages to kill the parasite. In an attempt to synthesize arginase inhibitors, six 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine derivatives with different substituents at the 4-position of the phenyl group were synthesized. All compounds were initially tested at 100 μM concentration against Leishmania amazonensis ARG (LaARG), showing inhibitory activity ranging from 36 to 74%. Two compounds, 1 (R=H) and 6 (R=CF3), showed arginase inhibition >70% and IC50 values of 12 μM and 47 μM, respectively. Thus, the kinetics of LaARG inhibition were analyzed for compounds 1 and 6 and revealed that these compounds inhibit the enzyme by an uncompetitive mechanism, showing Kis values, and dissociation constants for ternary complex enzyme-substrate-inhibitor, of 8.5 ± 0.9 μM and 29 ± 5 μM, respectively. Additionally, the molecular docking studies proposed that these two uncompetitive inhibitors interact with different LaARG binding sites, where compound 1 forms more H-bond interactions with the enzyme than compound 6. These compounds showed low activity against L. amazonensis free amastigotes obtained from mice lesions when assayed with as much as 30 μM. The maximum growth inhibition reached was between 20 and 30% after 48 h of incubation. These results suggest that this system can be promising for the design of potential antileishmanial compounds.

Synthesis method of pyrazolopyrimidine compounds

The invention relates to a synthesis method of pyrazolopyrimidine compounds. On the basis of the prior art, sodium iodide or potassium iodide is introduced to a hydrazinolysis reaction, the yield andthe purity are increased through the hydrazinolysis step, and accordingly, the total yield is increased. The method has the advantages of mild reaction conditions, high reaction yield and purity, lowproduction cost and the like, and is suitable for production on an industrialization scale.

Preparation method of pyrazolopyrimidine compound intermediate

The invention relates to medicine intermediates and especially provides a synthesis method of a pyrazolopyrimidine hydrazine compound. On the basis of the prior art, NaI or KI is added during a hydrazinolysis reaction, so that yield and purity in the hydrazinolysis reaction are increased. The method has gentle reaction conditions, high reaction yield and product purity, is low in production cost,and is suitable for industrial large-scale production.

Design and synthesis of pyrazolo[3,4-d]pyrimidines: Nitric oxide releasing compounds targeting hepatocellular carcinoma

A new series of pyrazolo[3,4-d]pyrimidines tethered with nitric oxide (NO) producing functionality was designed and synthesized. Sulforhodamine B (SRB) protein assay revealed that NO releasing moiety in the synthesized compounds significantly decreased the cell growth more than the des-NO analogues. Compounds 7C and 7G possessing N-para-substituted phenyl group, released the highest NO concentration of 4.6% and 4.7% respectively. Anti-proliferative activity of synthesized compounds on HepG2 cell line identified compounds 7h, 7p, 14a and 14b as the most cytotoxic compounds in the series of IC50?=?3, 5, 3 and 5?μM, respectively, compared to erlotinib as a reference drug (IC50?=?25?μM). Flow cytometry studies revealed that 7?h arrested the cells in G0/G1 phase of cell cycle while 7p arrested the cells in S phase. Moreover, docking study of the synthesized compounds on EGFR (PDB code: 1M17) and cytotoxicity study indicated that N-1 phenyl para substitution, pyrazole C-3 alkyl substitution and tethering the nitrate moiety through butyl group had a significant impact on the activity.

Application of compound in preparation of kallikrein KLK7 inhibition medicines, and synthesis method of compound

The invention belongs to the field of biomedicines, and especially relates to an application of a compound in the preparation of kallikrein KLK7 inhibition medicines, and a synthesis method of the compound. The structural formula of the compound is shown in the description. The compound for inhibiting the kallikrein KLK7 can effectively inhibit the activity of the KLK7, the synthesis method of the compound is simple and is easy to implement, and proper auxiliary materials and assistants can be added to prepare medicinal preparations for inhibiting the activity of the KLK7.