64096-89-5

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-1-(2-CHLOROPHENYL)-1H-PYRAZOLE-4 is used as a key intermediate in the synthesis of pharmaceutical drugs for its potential to contribute to the development of new therapeutic agents. Its unique structure allows for the creation of molecules with specific biological activities, making it a promising candidate for drug discovery and medicinal chemistry research.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 5-AMINO-1-(2-CHLOROPHENYL)-1H-PYRAZOLE-4 is used as a starting material for the preparation of organic compounds with targeted properties. Its ability to be modified and combined with other chemical entities facilitates the design and synthesis of novel molecules with potential therapeutic effects.
Used in Drug Development:
5-AMINO-1-(2-CHLOROPHENYL)-1H-PYRAZOLE-4 is utilized in drug development as a component in the creation of new pharmaceutical entities. Its structural attributes make it suitable for the design of molecules that can interact with biological targets, potentially leading to the discovery of new drugs with improved efficacy and selectivity.
Used in Organic Chemistry:
As a heterocyclic compound, 5-AMINO-1-(2-CHLOROPHENYL)-1H-PYRAZOLE-4 is used in organic chemistry for its potential in forming a wide range of chemical reactions and transformations. Its reactivity and functional group compatibility make it a valuable component in the synthesis of complex organic molecules and materials.

Upstream product

• 123-06-8 Ethoxymethylenemalononitrile 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 122-51-0 orthoformic acid triethyl ester 
• 109-77-3 malononitrile 
• 41052-75-9 o-chlorophenylhydrazine hydrochloride 
• 5417-82-3 (1-ethoxyethylidene)malononitrile 
• 95-51-2 o-chloroaniline 

Downstream Products

• 5334-45-2 N-[2-(2-chloro-phenyl)-4-cyano-2H-pyrazol-3-yl]-acetamide 
• 102353-66-2 1-(2-chloro-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine 
• 135108-51-9 4-Amino-1-(2-chloro-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 64096-91-9 4H-Pyrazolo<1,5-a>benzimidazole-3-carbonitrile 
• 792953-14-1 5-amino-1-(2-chloro-phenyl)-1H-pyrazole-4-carboxylic acid amide 
• 5334-46-3 6-methyl-1-(2-chlorophenyl)-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one 
• 577757-11-0 C₁₇H₁₃ClN₆OS₂ 
• 1415025-09-0 C₂₃H₁₇ClN₆OS₂ 
• 1415025-10-3 C₁₇H₁₃ClN₆O₂S 
• 1207760-80-2 2-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-N-(4-methyl-1,3-thiazol-2-yl)hexanamide 
• 1207760-58-4 2-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-4-methoxy-N-(5-methylpyridin-2-yl)butanamide 
• 1006597-09-6 1-(2-chloro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 
• 1214527-18-0 C₁₄H₁₂ClN₅O 
• 1613037-27-6 5-[5-amino-1-(2'-chlorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 

Relevant academic research and scientific papers

Effectiveness of novel 5-(5-amino-1-aryl-1H-pyrazol-4-yl)-1H-tetrazole derivatives against promastigotes and amastigotes of leishmania amazonensis

In this research, a series of substituted 5-(5-amino-1-aryl-1H-pyrazol-4- yl)-1H-tetrazoles were synthesized and evaluated for in vitro antileishmanial activity. Among the derivatives, examined compounds 3b and 3l exhibited promising activity against promastigotes and amastigotes forms of Leishmania amazonensis. The cytotoxicity of these compounds was evaluated on murine cells, giving access to the corresponding selectivity index (SI).

The discovery of a novel series of glucokinase activators based on a pyrazolopyrimidine scaffold

Glucokinase is a key enzyme in glucose homeostasis since it phosphorylates glucose to give glucose-6-phosphate, which is the first step in glycolysis. GK activators have been proven to lower blood-glucose, and therefore have potential as treatments for type 2 diabetes. Here the discovery of pyrazolopyrimidine GKAs is reported. An original singleton hit from a high-throughput screen with micromolar levels of potency was optimised to give compounds with nanomolar activities. Key steps in this success were the introduction of an extra side-chain, which increased potency, and changing the linking functionality from a thioether to an ether, which led to improved potency and lipophilic ligand efficiency. This also led to more stable compounds with improved profiles in biological assays.

Structure-based discovery of highly selective phosphodiesterase-9A inhibitors and implications for inhibitor design

A new series of phosphodiesterase-9 (PDE9) inhibitors that contain a scaffold of 6-amino-pyrazolopyrimidinone have been discovered by a combination of structure-based design and computational docking. This procedure significantly saved the load of chemical synthesis and is an effective method for the discovery of inhibitors. The best compound 28 has an IC50 of 21 nM and 3.3 μM, respectively, for PDE9 and PDE5 and about 3 orders of magnitude of selectivity against other PDE families. The crystal structure of the PDE9 catalytic domain in complex with 28 has been determined and shows a hydrogen bond between 28 and Tyr424. This hydrogen bond may account for the 860-fold selectivity of 28 against PDE1B, in comparison with about 30-fold selectivity of BAY73-6691. Thus, our studies suggest that Tyr424, a unique residue of PDE8 and PDE9, is a potential target for improvement of selectivity of PDE9 inhibitors.

An efficient synthesis of new 5-(1-Aryl-1H-pyrazole-4-yl)-1H-tetrazoles from 1-Aryl-1H-pyrazole-4-carbonitriles via [3 + 2] cycloaddition reaction

A series of new 5-(1-aryl-1H-pyrazole-4-yl)-1H-tetrazoles 4a-l were synthesized via [3 + 2] cycloaddition reaction from 1-aryl-1H-pyrazole-4- carbonitriles 3a-l, sodium azide and ammonium chloride, using dimethylformamide (DMF) as solvent, in good yields: 64-85%. The structures of these newly synthesized compounds were determined from the IR, 1H- and 13C-NMR spectroscopic data and elemental analyses.

Discovery and evaluation of 7- lkyl-1,5-bis-aryl-pyrazolopyridinones as Highly potent, selective, and orally efficacious inhibitors of p38α mitogen-activated protein kinase

The p38α mitogen-activated protein (MAP) kinase is a central signaling molecule in many proinflammatory pathways, regulating the cellular response to a multitude of external stimuli including heat, ultraviolet radiation, osmotic shock, and a variety of cytokines especially interleukin-1- and tumor necrosis factor α. Thus, inhibitors of this enzyme are postulated to have significant therapeutic potential for the treatment of rheumatoid arthritis, inflammatory bowel disease, and Crohn's disease, as well as other diseases where aberrant cytokine signaling is the driver of disease. In this communication, we describe a novel class of 7-alkyl-1,5-bis-aryl- pyrazolopyridinone-based p38α inhibitors. In particular, compound 3f is highly potent in the enzyme and cell-based assays, selective in an Ambit kinase screen, and efficacious (ED50 - 0.01 mg/kg) in the rat collagen induced arthritis (CIA) model.

Microwave-assisted protocols for the expedited synthesis of pyrazolo[1,5-a] and [3,4-d]pyrimidines

General, high-yielding MAOS protocols for the expedited synthesis of functionalized pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-b]pyrimidines, as well as their pyrazole precursors, are described amenable to an iterative analogue library synthesis strategy for lead optimization.

Positive allosteric modulators of the metabotropic glutamate receptor subtype 4 (mGluR4): Part I. Discovery of pyrazolo[3,4-d]pyrimidines as novel mGluR4 positive allosteric modulators

This letter describes the synthesis and SAR, developed through an iterative analogue library approach, of an mGluR4 positive allosteric modulator lead based on a pyrazolo[3,4-d]pyrimidine scaffold. Despite tremendous therapeutic potential, Compound 7, VU0080421, and related congeners represent only a handful of mGluR4 positive allosteric modulators ever described.

Aryl substituted purine analogues

Aryl-substituted purine analogues are provided, of the formula: (I) wherein variables are as described herein. Such compounds are ligands that may be used to modulate specific receptor activity in vivo or in vitro, and are particularly useful in the treat

6-Arylmethyl-substituted pyrazolopyrimidines

The invention relates to novel 6-arylmethyl-substituted pyrazolopyrimidines, process for their preparation and their use for producing medicaments for improving perception, concentration, learning and/or memory.

6-ARYLMETHYL-SUBSTITUTED PYRAZOLOPYRIMIDINES

The invention relates to novel 6-arylmethyl-substituted pyrazolopyrimidines of formula (I) wherein R1 represents phenyl, pyridyl or thiophenyl, and R2 represents phenyl or heteroaryl. The invention also relates to the salts and solvates thereof, and/or solvates of the salts thereof, to methods for producing said pyrazolopyrimidines, and to the use of the same for producing pharmaceuticals for improving perception, power of concentration, learning capacity and/or memory retention.