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Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Bromophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine is used as an enzyme inhibitor for its potential to modulate biological processes by inhibiting specific enzymes, which can be crucial in the development of new drugs for various diseases.
Used in Cancer Research:
In cancer research, 1-(4-Bromophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine is used as a potential anti-cancer agent. Its study aims to understand its effects on cancer cells and to explore its potential to be developed into a therapeutic agent for cancer treatment.
Used in Treatment of Inflammatory and Autoimmune Diseases:
1-(4-Bromophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine is also being studied for its potential use in the treatment of inflammatory and autoimmune diseases. Its role as a potential therapeutic agent is based on its capacity to influence the immune response and reduce inflammation, which are key factors in these types of conditions.

Upstream product

• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 1231710-82-9 5-{[2-(4-bromophenyl)hydrazono]methyl}-4,6-dichloropyrimidine 
• 5334-28-1 5-amino-1-(4-bromophenyl)-1H-pyrazole-4-carbonitrile 
• 589-21-9 (4-bromophenyl)hydrazine 
• 1429924-49-1 5-((2-(4-bromophenyl)hydrazono)methyl)-4,6-dichloropyrimidine 
• 106-40-1 4-bromo-aniline 
• 864872-05-9 1-(4-bromo-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 

Downstream Products

• 887327-49-3 [1-(4-bromo-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-o-tolyl-amine 
• 940311-36-4 N-{3-[1-(4-bromophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-4-methyl-phenyl}-3-trifluoromethyl-benzamide 

Relevant academic research and scientific papers

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.

Synthesis of 1,4-disubstituted pyrazolo[3,4-d]pyrimidines from 4,6-dichloropyrimidine-5-carboxaldehyde: Insights into selectivity and reactivity

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5- carboxaldehyde with both aromatic and aliphatic hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective, high-yielding, and operationally simple manner are presented. For aromatic hydrazines, the reaction is performed at a high temperature in the absence of an external base. For aliphatic hydrazines, the reaction proceeds at room temperature in the presence of an external base. The observed selectivity and reactivity trends are rationalized through consideration of the proposed reaction mechanism. The 1-substituted 4-chloropyrazolo[3,4-d]pyrimidine products serve as versatile synthetic intermediates, through further functionalization of the 4-chloride moiety, enabling the rapid generation of a structurally diverse array of 1,4-disubstituted pyrazolo[3,4-d]pyrimidines. Georg Thieme Verlag Stuttgart. New York.

Selective synthesis of 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5- carboxaldehyde with various hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective and high-yielding manner are presented. For aromatic hydrazines, the reaction is performed in the absence of an external base, which promotes exclusive hydrazone formation. The hydrazones subsequently cyclize at an elevated temperature to form the desired pyrazolo[3,4-d]pyrimidine products. For aliphatic hydrazines, the reaction sequence proceeds as a single step in the presence of an external base.

N-N bond-forming cyclization for the one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines

An efficient one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines in good yield and under mild reaction conditions is described. By exploiting electron-deficient hydroxylamines, the substituted oxime products were formed with very high E-diastereoselectivity. The key step utilizes a cyclization reaction upon an oxime derived from hydroxylamine-O-sulfonic acid to form the N-N bond of the product.

3-(SUBSTITUTED AMINO)-PYRAZOLO[3,4-d]PYRIMIDINES AS EPHB AND VEGFR2 KINASE INHIBITORS

The invention relates to novel pyrazolo[3,4-d]pyrimidines of the formula in which all of the variables are as defined in the specification, in free form or in salt form, to their preparation, to their use as medicaments and to medicaments comprising them.

1,4 SUBSTITUTED PYRAZOLOPYRIMIDINES AS KINASE INHIBITORS

The invention relates to 1,4-substituted pyrazolopyrimidine compounds of the formula (I), pharmaceuticals comprising a 1,4-substituted pyrazolopyrimidine compound, the use of a 1,4-substituted pyrazolopyrimidine compound in the treatment or the use thereof in the manufacture of a pharmaceutical formulation for the treatment of a disease that depends on inadequate activity of a protein kinase, methods of treatment comprising administering a 1,4-substituted pyrazolopyrimidine compound, methods for the manufacture of a novel compound of that class, and novel intermediates and partial steps for their synthesis.

PYRAZOLOPYRIMIDINES AS ANTI - HEPATITS C AGENTS

Pyrazolopyrimidine derivatives of formula (I), or a pharmaceutically acceptable salt thereof, are found to be active against hepatitis C infection, wherein: R1 is C6-C10 aryl, 5- to 10- membered heteroary1, -(C1-C4 alkyl)-(C6-C10 aryl) or -(C1-C4 alkyl)-(5- to 10- membered heteroaryl); R2 is a C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heteroaryl or 5- to 10- membered heterocyclyl moiety, said moiety being optionally fused to a C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heteroaryl or 5- to 10-membered heterocyclic ring; and X is -NR'-, -NR'-CO-NR''-, -NR'-L, or -NR'-CO-L-, wherein R' and R'' are the same or different and each represent hydrogen or a C1-C6 alkyl group and L represents a C1-C6 alkylene group, the aryl, heteroaryl, heterocyclyl. and carbocyclyl moieties in the R1 and R2 substituents being unsubstituted or substituted by 1, 2 or 3 substituents selected from halogen, C1-C4 alkyl C1-C4alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano, nitro, C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heterocyclyl, 5- to 10- membered heteroaryl, -NR'-CO2-R'', -CO2R'', -COR'''-NR'-CO-R''',-CONR'R'',SO2NR'R'',SO2R'''and -O-(CH2)n-R''' substituents, wherein n is from 0 to 4, each R’is the same or different and is hydrogen or C1-C6 alkyl, each R'' is the same or different and is hydrogen, C1-C6 alkyl, C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heteroaryl, each R''' is the same or different and is C1-C6 alkyl, C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heteroaryl, and each R'''' is the same or different and is C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heterocryl, the aryl, heteroaryl, heterocyclyl and carbocyclyl moieties in said substituents being unsubstituted or substituted by a further substituent selected from C1-C4 alkyl, C1-C4 hydroxyalkyl and C1-C4 haloalkyl groups.