5334-30-5

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine is used as an intermediate in the preparation of various enzymatic inhibitors. It plays a crucial role in the development of therapeutic agents targeting specific enzymes, which are often involved in disease progression.
Used in Biochemical Research:
In the field of biochemical research, 1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine serves as a valuable compound for studying the structure-activity relationships of enzymatic inhibitors. Its unique structure allows researchers to investigate the interactions between the compound and its target enzymes, leading to a better understanding of the underlying mechanisms and the potential for designing more effective inhibitors.
Used in the Development of Anticancer Agents:
1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine is used as a building block for the synthesis of small molecule inhibitors targeting the Src family of non-receptor tyrosine kinases. These kinases are known to regulate cell adhesion, growth, and differentiation through the activation of multiple intracellular signaling pathways. Abnormal activation of Src kinases has been associated with various cancers, making them an attractive therapeutic target. By incorporating 1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine into the structure of Src kinase inhibitors, researchers aim to develop more potent and selective agents to combat cancer.
Used in Drug Delivery Systems:
1-Phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine may also find application in the development of drug delivery systems, particularly for the targeted delivery of enzymatic inhibitors. Its structural properties could be exploited to enhance the solubility, stability, and bioavailability of these inhibitors, ultimately improving their therapeutic efficacy.

Biological Activity

Negative control for the src kinase inhibitor PP 2 (3-(4-chlorophenyl)1-(1,1-dimethylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine ). Inhibits EGFR kinase (IC 50 = 2.7 μ M).

InChI:InChI=1/C11H9N5/c12-10-9-6-15-16(11(9)14-7-13-10)8-4-2-1-3-5-8/h1-7H,(H2,12,13,14)

Upstream product

• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 77287-34-4 formamide 
• 5334-48-5 4-chloro-1-(phenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 100-63-0 phenylhydrazine 
• 108-86-1 bromobenzene 
• 2380-63-4 4-Aminopyrazolo<3,4-d>pyrimidin 
• 591-50-4 iodobenzene 
• 62564-59-4 ethyl N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)formimidate 

Downstream Products

• 21314-17-0 1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 87412-76-8 1-phenyl-4-(p-anisyl)pyrazolo<3,4-d>pyrimidine 
• 87412-74-6 1-phenyl-4-(m-anisyl)pyrazolo<3,4-d>pyrimidine 
• 87412-75-7 1-phenyl-4-(o-anisyl)pyrazolo<3,4-d>pyrimidine 
• 87412-79-1 1-phenyl-4-(p-chlorophenyl)pyrazolo<3,4-d>pyrimidine 
• 87412-78-0 1-phenyl-4-(o-chlorophenyl)pyrazolo<3,4-d>pyrimidine 
• 87412-77-9 1-phenyl-4-(m-chlorophenyl)pyrazolo<3,4-d>pyrimidine 
• 87412-72-4 1-phenyl-4-(m-tolyl)pyrazolo<3,4-d>pyrimidine 
• 87412-73-5 1-phenyl-4-(o-tolyl)pyrazolo<3,4-d>pyrimidine 
• 87432-51-7 1-phenyl-4-(pentyloxy)-1H-pyrazolo<3,4-d>pyrimidine 
• 53645-78-6 1-phenyl-4-phenylpyrazolo<3,4-d>pyrimidine 
• 1454789-02-6 6-cyano-7-imino-5-ethyl-N¹-phenyl-1, 7-dihydropyrazolo[3', 4':4, 5]pyrimido[1, 6-a]pyrimidine 
• 1454789-01-5 6-cyano-7-imino-N¹-phenyl-1,7-dihydropyrazolo[3',4':4,5]pyrimido[1,6-a]pyrimidine 
• 1448550-36-4 C₂₅H₂₃N₇O₂ 

Relevant academic research and scientific papers

Synthesis and characterization of two novel organic-inorganic compounds based on tetrahexyl and Tetraheptyl ammonium ions and the preyssler anion and their catalytic activities in the synthesis of 4-aminopyrazolo[3,4-d]- pyrimidines

Two novel organic-inorganic compounds based on tetrahexylammonium (THA) and tetraheptylammonium (THPA) ions and the Preyssler anion, [NaP5W30O110]14-, were synthesized and formulated as (THA)7.7H6.3 [NaP5W30O110] (A) and (THPA)7.5 H6.5[N aP5W30O110] (B).

Copper-Catalyzed N1 Coupling of 3-Aminoindazoles and Related Aminoazoles with Aryl Bromides

The N1-selective arylation of 3-aminoindazoles using copper catalysis is herein reported. The reaction uses readily accessible aryl bromides as coupling partners, including those from heterocycles, and allows easy access to a broad variety of substituted 3-aminoindazoles. The methodology was also examined on other aminoazoles of interest for the pharmaceutical industry.

Pyrimidine compound with pyrazolo [3, 4-d] as parent nucleus and preparation method thereof

The invention discloses a pyrimidine compound with pyrazolo [3, 4-d] as a parent nucleus and a preparation method thereof. The invention relates to pyrazolo [3, 4-d] pyrimidine derivatives shown in ageneral formula (I), a preparation method of the pyrazol

Synthesis and pharmacological evaluation of pyrazolopyrimidopyrimidine derivatives: Anti-inflammatory agents with gastroprotective effect in rats

We report the synthesis of new anti-inflammatory 1,7- dihydropyrazolo[3′,4′:4,5]pyrimido[1,6-a]pyrimidine 5 from aminocyanopyrazole. All compounds were characterized by physical, chemical and spectral studies. Preliminary pharmacological evaluation of the resulting products showed that compounds 5a, b, f (50-100 mg/kg, i.p) are active anti-inflammatory agents in carrageenan-induced rat paw oedema assay, and their effects are comparable to that of acetylsalicylic-lysine (300 mg/kg, i.p.), used as a reference drug. The nature of substituent (Y, R3) had a pronounced effect on the anti-inflammatory activity. Studies of structure-activity relationships have led to selection of compound ethyl-3,5-dimethyl-7-imino-N 1-phenyl-1,7-dihydropyrazolo[3′, 4′:4,5]pyrimido[1,6-a]pyrimidine-6-carboxylate, 5f which exhibited the most potent anti-inflammatory activity. In addition, the compounds 5a, b, f showed a significant gastroprotective effect against HCl/EtOH-induced gastric ulcer.

Novel pyrazolopyrimidine derivatives targeting COXs and iNOS enzymes; Design, synthesis and biological evaluation as potential anti-inflammatory agents

A novel set of 4-substituted-1-phenyl-pyrazolo[3,4-d]pyrimidine and 5-substituted-1-phenyl-pyrazolo[3,4-d]pyrimidin-4-one derivatives were synthesized and evaluated as potential anti-inflammatory agents. The newly prepared compounds were assessed through the examination of their in vitro inhibition of four targets; cyclooxygenases subtypes (COX-1 and COX-2), inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-κB). Compounds 8a, 10c and 13c were the most potent and selective ligands against COX-2 with inhibition percentages of 79.6%, 78.7% and 78.9% at a concentration of 2 μM respectively, while compound 13c significantly inhibited both COX subtypes. On the other hand, fourteen compounds showed high iNOS inhibitory activities with IC50 values in the range of 0.22-8.5 μM where the urea derivative 11 was the most active compound with IC50 value of 0.22 μM. Most of the tested compounds were found to be devoid of inhibitory activity against NF-kB. Moreover, almost all compounds were not cytotoxic, (up to 25 μg/ml), against a panel of normal and cancer cell lines. The in silico docking results were in agreement with the in vitro inhibitory activities against COXs and iNOS enzymes. The results of in vivo anti-inflammatory and antinociceptive studies were consistent with that of in vitro studies which confirmed that compounds 8a, 10c and 13c have significant anti-inflammatory and analgesic activities comparable to that of the control, ketorolac. Taken together, dual inhibition of COXs and iNOS with novel pyrazolopyrimidine derivatives is a valid strategy for the development of anti-inflammatory/ analgesic agents with the probability of fewer side effects.

Synthesis of new pyrazole and antibacterial pyrazolopyrimidine derivatives

3-Substituted-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines 2a-c were synthesized by treating 5-aminopyrazole- 4-carbonitriles 1a-c with formamide. The reactivity of compounds 1a-c towards some cyclic anhydrides was studied. The condensation of 5-aminopyrazole-4-carbonitrile 1b with triethylorthoformate gives imidate 7b, which reacts with a series of primary amines and leads to pyrazolo[3,4-d]pyrimidine-4-amines 9 and 10. The reaction of imidate 7b with ammonia and hydroxylamine afforded pyrazolopyrimidine 2b and pyrazolo[3,4-d]pyrimidin-5-(4H) -ol 11, respectively. The synthesized compounds were completely characterized by 1H NMR, 13C NMR, IR, and HRMS. The antibacterial activity of some new synthesized compounds was evaluated and appeared to be signiflcant. Tubitak.

Synthesis and biological evaluation of some novel fused pyrazolopyrimidines as potential anticancer and antimicrobial agents

Synthesis and evaluation of anticancer and antimicrobial activity of some novel pyrazolopyrimidines and fused pyrazolopyrimidines are reported. Twelve analogs were selected to be evaluated for their in vitro anticancer potential against a panel of three h