826-85-7

Usage

Uses

Used in Pharmaceutical Synthesis:
5-Amino-1-phenylpyrazole is used as a reagent in the synthesis of sulfaphenazole (S689020) derivatives. These derivatives are employed as inhibitors and tools for comparing active sites of human liver cytochromes P450 2C subfamily. This application is crucial in understanding the structure and function of these enzymes, which play a vital role in drug metabolism and detoxification processes.
In the pharmaceutical industry, 5-Amino-1-phenylpyrazole is used as a building block for the development of new drugs targeting the cytochrome P450 2C subfamily. By inhibiting or modulating the activity of these enzymes, it is possible to improve the efficacy and safety of various medications.
Additionally, 5-Amino-1-phenylpyrazole can be used in the synthesis of other bioactive compounds with potential therapeutic applications. Its versatile chemical properties make it a valuable component in the development of novel pharmaceutical agents.

InChI:InChI=1/C9H9N3/c10-9-6-7-11-12(9)8-4-2-1-3-5-8/h1-7H,10H2

Upstream product

• 16078-71-0 ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate 
• 26955-79-3 3-(N'-phenyl-hydrazino)-propionitrile 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 25112-05-4 cyanoacetaldehyde phenylhydrazone 
• 60838-50-8 3-methoxy-2-propenenitrile 
• 100-63-0 phenylhydrazine 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 
• 124-41-4 sodium methylate 
• 59-88-1 phenylhydrazine hydrochloride 
• 1225387-53-0 3⁽⁵⁾-aminopyrazole 
• 98-80-6 phenylboronic acid 
• 62-53-3 aniline 
• 591-50-4 iodobenzene 
• 1820-80-0 3-aminopyrazole 

Downstream Products

• 855-91-4 N₄-Acetylsulfaphenazole 
• 77746-64-6 1-Phenyl-5-{[1-piperidin-1-yl-meth-(E)-ylidene]-amino}-1H-pyrazole-4-carbaldehyde 
• 77746-71-5 N,N-Dimethyl-N'-(2-phenyl-2H-pyrazol-3-yl)-formamidine 
• 77746-55-5 N'-(4-Formyl-2-phenyl-2H-pyrazol-3-yl)-N,N-dimethyl-formamidine; hydrochloride 
• 2868-42-0 4,6-dimethyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine 
• 93734-41-9 (E)-ethyl 2-cyano-3-((1-phenyl-1H-pyrazol-5-yl)amino)acrylate 
• 54844-13-2 carbethoxy-5 dihydro-3,6 oxo-6 phenyl-2 pyrazolo <2,4-b> pyridine 
• 79442-87-8 N-(1-phenylpyrazol-5-yl)-2-hydroxybenzamide 
• 57047-10-6 3-Methyl-5-methylamino-1-phenyl-1H-pyrazole 
• 79442-80-1 2-Methoxy-N-(5-methyl-2-phenyl-2H-pyrazol-3-yl)-benzamide 
• 79442-83-4 N-[1,5-Dimethyl-2-phenyl-1,2-dihydro-pyrazol-(3E)-ylidene]-2-hydroxy-benzamide 
• 79442-79-8 2-Methoxy-N-(2-phenyl-2H-pyrazol-3-yl)-benzamide 
• 79442-82-3 2-Hydroxy-N-[1-methyl-2-phenyl-1,2-dihydro-pyrazol-(3E)-ylidene]-benzamide 
• 1482-35-5 1-phenyl-5-methylaminopyrazole 

Relevant academic research and scientific papers

Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water

The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H2TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C–N coupling reactions of arylboronic acids and amines (Chan–Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan–Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.

Deciphering the robustness of pyrazolo-pyridine carboxylate core structure-based compounds for inhibiting α-synuclein in transgenic C. elegans model of Synucleinopathy

Parkinson's disease (PD), a calamitous neurodegenerative disorder with no cure till date, is closely allied with the misfolding and aggregation of α-Synuclein (α -Syn). Inhibition of α-Syn aggregation is one of the optimistic approaches for the treatment for PD. Here, we carried out hypothesis-driven studies towards synthesising a series of pyrazolo-pyridine carboxylate containing compounds (7a–7m) targeted at reducing deleterious α-Syn aggregation. The target compounds were synthesized through multi-step organic synthesis reactions. From docking studies, compounds 7b, 7g and 7i displayed better interaction with the key residues of α-Syn with values: ?6.8, ?8.9 and ?7.2 Kcal/mol, respectively. In vivo transgenic C. elegans model of Synucleinopathy was used to evaluate the ability of the designed and synthesized compounds to inhibit α-Syn aggregation. These lead compounds 7b, 7g and 7i displayed 1.7, 2.4 and 1.5-fold inhibition of α-Syn with respect to the control. Further, the strategy of employing pyrazolo-pyridine-based compounds worked with success and these scaffolds could be further modified and validated for betterment of endpoints associated with PD.

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY

This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that inhibit (e.g., antagonize) Stimulator of Interferon Genes (STING). Said chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) STING activation (e.g., STING signaling) contributes to the pathology and/or symptoms and/or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also features compositions containing the same as well as methods of using and making the same.

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY

This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that inhibit (e.g., antagonize) Stimulator of Interferon Genes (STING). Said chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) STING activation (e.g., STING signaling) contributes to the pathology and/or symptoms and/or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also features compositions containing the same as well as methods of using and making the same.

Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt

A synthesis of fluorinated pyrimidines under mild conditions from amidine hydrochlorides and the recently described potassium 2-cyano-2-fluoroethenolate was developed. A broad substrate scope was tested and mostly excellent yields were obtained. The synthesis of fluorinated aminopyrazoles from the same fluorinated precursor could be demonstrated but proceeded with lower efficiency.

Synthesis of new conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and evaluation against leishmania amazonensis

In this research three series of substituted 1H-pyrazolo[3,4-b]pyridine phosphoramidates were synthesized and characterized by infrared,1H,13C, and31P nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. The products were obtained in good yields (67-83percent) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chloro-1H-pyrazolo[3,4-b]pyridines. These compounds were evaluated as antileishmanials against Leishmania amazonensis promastigotes in vitro. Among all, compounds of a series showed expressive antileishmanial activity. Two of them emerged as the most active, with IC50 values of 6.44 ± 1.49 and 12.25 ± 0.68 μM. The cytotoxicity of this series was assessed on murine cells and presented values similar to the reference drug pentamidine.

Thermal Ring-Opening of Pyrazolo[3,4-d][1,2,3]triazin-4-ones: An Experimental and Theoretical Study

Several 3-pyrazolylcarbonyl-pyrazolo[3,4-d][1,2,3]triazin-4-ones have been prepared from 5-amino-1H-pyrazole-4-carbonitriles through a simple sequence. In the first step, diazotization of the corresponding aminopyrazoles afforded pyrazolo[3,4-d][1,2,3]triazin-4-ones. Next, thermal rearrangement of these compounds through nitrogen elimination gave the final products. The proposed mechanism for the ring-opening of the pyrazolotriazinones to give the pyrazolylcarbonyl-pyrazolotriazinones involves the generation of an iminoketene intermediate, which reacts with a second molecule of pyrazolotriazinone. The complete mechanism of product formation involving the iminoketene intermediate, and all other reasonable pathways, have been explored in detail through DFT calculations. Furthermore, additional experiments to corroborate the presence of the iminoketene intermediate were carried out.

Harnessing Cascade Suzuki-Cyclization Reactions of Pyrazolo[3,4-b]pyridine for the Synthesis of Tetracyclic Fused Heteroaromatics

Numerous procedures have been described for the functionalization of pyrazolo[3,4-b]pyridine, mainly involving nucleophilic substitutions at the C-4 position or esterifications/amidations at the C-5 position. In this paper, we describe a robust, easy to implement protocol for the Suzuki cross-coupling reaction of chloroarene 2, followed by in-situ lactonization to provide chromenopyrazolopyridines. The extension of the scope of the reaction to fused naphthyridinones is also reported. This strategy gave access to 10 original pyrazolopyridine-containing tetracyclic compounds.

Design, synthesis and anti-P. falciparum activity of pyrazolopyridine–sulfonamide derivatives

Ten 1-phenyl-1H-pyrazolo[3,4-b]pyridine derivatives connected by a linker group to benzenesulfonamide moieties with different substituents in the 4-position were synthesized and assayed against Plasmodium falciparum. These ten compounds exhibited activity in vitro against the chloroquine-resistant clone W2 with IC50values ranging from 3.46 to 9.30 μM. The most active derivatives with substituent R2= Cl or CH3at the benzenesulfonamide moiety exhibited the lowest IC50. Compounds with an R1= CO2Et substituent at the 5-position of the 1H-pyrazolo[3,4-b]pyridine ring presented lower activity than those with a CN substituent. The 1H-pyrazolo[3,4-b]pyridine system appears to be promising for further studies as an antimalarial for overcoming the burden of resistance in P. falciparum.

Copper(I)/Copper(II)-Assisted Tandem Catalysis: The Case Study of Ullmann/Chan-Evans-Lam N1,N3-Diarylation of 3-Aminopyrazole

Unprecedented CuI/CuII-assisted tandem catalysis allowing an Ullmann/Chan-Evans-Lam sequence was achieved. This three-component, one-pot reaction triggered by a change in the oxidation state of the metal leads to the selective N1,N3-diarylation of 3-aminopyrazole. This new method should be a valuable tool for small-molecule drug discovery that requires suitable regio- and/or chemoselective strategies for the N-arylation of nitrogen-containing heterocycles. Tandem power: The first assisted tandem copper-catalyzed process, triggered by a change in the oxidation state of the metal, is developed to allow a one-pot Ullman/Chan-Evans-Lam sequence leading to the selective N1,N3-diarylation of 3-aminopyrazole.