5334-48-5

Basic information

• Product Name: 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE
• Synonyms: 4-chloro-1-phenyl-pyrazolo[3,4-d]pyrimidine;4-chloro-1-phenylpyrazolo[3,4-d]pyrimidine;NSC 1425
• CAS NO: 5334-48-5
• Molecular Formula: C₁₁H₇ClN₄
• Molecular Weight: 230.66
• Mol File: 5334-48-5.mol

Chemical Properties

• Boiling Point: 323.7°Cat760mmHg
• Flash Point: 149.6°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 0.000257mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(5334-48-5)
• EPA Substance Registry System: 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(5334-48-5)

Safety Data

• Hazardous Substances Data: 5334-48-5(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is used as a research tool for studying various biological processes and mechanisms due to its unique chemical properties and potential interactions with biological targets.
Used in Drug Development:
In the pharmaceutical industry, 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is used as a lead compound for the development of new drugs. Its pharmacological activities and structural features make it a promising candidate for further optimization and synthesis of more effective therapeutic agents.
Used as a Building Block in Medicinal Chemistry:
4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is utilized as a key component in the synthesis of new pharmaceutical compounds, leveraging its reactivity and structural attributes to create innovative and effective medications.
Used in Protein Kinase Inhibition Research:
4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is studied for its potential as a protein kinase inhibitor, which is significant in the treatment of various diseases and conditions where protein kinases play a crucial role in their progression.
Used in Anticancer Applications:
4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is used as an anticancer agent, given its potential to target and inhibit specific pathways involved in cancer cell growth and proliferation.
Used in Antifungal Applications:
In the field of antifungal therapy, 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is used to combat fungal infections, leveraging its antifungal properties to inhibit fungal growth and reduce infection.
Used in Anti-inflammatory Applications:
4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is employed as an anti-inflammatory agent, potentially mitigating inflammation by modulating the immune response and reducing inflammation-associated symptoms.

InChI:InChI=1/C11H7ClN4/c12-10-9-6-15-16(11(9)14-7-13-10)8-4-2-1-3-5-8/h1-7H

Upstream product

• 21314-17-0 4-hydroxy-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 59-88-1 phenylhydrazine hydrochloride 
• 100-63-0 phenylhydrazine 
• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 16078-71-0 ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate 
• 1429924-37-7 4,6-dichloro-5-((2-phenylhydrazono)methyl)pyrimidine 
• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 77287-34-4 formamide 
• 62-53-3 aniline 
• 14160-96-4 4-chloro-6-(phenylamino)pyrimidine-5-carbaldehyde 
• 1383927-17-0 (E)-(4-chloro-6-(phenylamino)pyrimidin-5-yl)methyleneaminooxysulfonic acid 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 21314-17-0 1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 

Downstream Products

• 130235-58-4 (1-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-thiophen-2-yl-methanone 
• 89549-85-9 Benzoic acid cyano-(4-nitro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methyl ester 
• 89549-77-9 Benzoic acid cyano-phenyl-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methyl ester 
• 89549-81-5 Benzoic acid (4-chloro-phenyl)-cyano-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methyl ester 
• 59563-95-0 (1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-p-tolyl-methanone 
• 89549-55-3 (4-Fluoro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 59563-90-5 (4-chloro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 59563-88-1 (2-chloro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 130235-57-3 Naphthalen-1-yl-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 130235-55-1 N-[4-(1-Phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-carbonyl)-phenyl]-acetamide 
• 89549-84-8 Benzoic acid cyano-(4-cyano-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methyl ester 
• 59563-84-7 phenyl-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 89549-57-5 4-phenyl-4,5-dihydro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carboxylic acid 
• 130235-60-8 (3,4-Dimethoxy-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 

Relevant articles and documents

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.

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, 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.

ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE 1 (ENPP-1) INHIBITORS AND USES THEREOF

Disclosed herein are methods and compounds of augmenting and enhancing the production of type I IFNs in vivo. In some embodiments, the compounds disclosed herein are ENPP-1 inhibitors, pharmaceutical compositions, and methods for the treatment of cancer or a viral infection.

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.

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.

PYRAZOLOPYRIMIDINE ANTIBACTERIAL AGENTS

Pyrazolopyrimidine compounds for inhibition of isoprenoid biosynthesis have a formula (I) or a pharmaceutically acceptable salt thereof. In formula (I), R1 includes an alkyl group and R2 includes an optionally substituted moiety selected from the group consisting of an optionally substituted benzyl group, an optionally substituted phenethyl group, an optionally substituted ethanol group, an optionally substituted ethyl acetate group, an optionally substituted methyl furan group, an optionally substituted 3-ethyl indole group, and a lower alkyl group. Compositions containing pyrazolopyrimidine compounds and methods for using pyrazolopyrimidine compounds are described.

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.