40401-41-0

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-CHLORO-PHENYL)-5-METHYL-2H-PYRAZOL-3-YLAMINE is used as a key intermediate in the development of new drugs targeting specific biological pathways. Its unique chemical structure allows it to interact with various biological targets, making it a promising candidate for the creation of innovative therapeutic agents.
Used in Organic Synthesis:
2-(3-CHLORO-PHENYL)-5-METHYL-2H-PYRAZOL-3-YLAMINE serves as a building block for the creation of other compounds with similar structures or properties. Its reactivity and functional groups make it a valuable component in the synthesis of complex organic molecules, contributing to the advancement of chemical research and development.
Used in Chemical Research:
The unique chemical structure and reactivity of 2-(3-CHLORO-PHENYL)-5-METHYL-2H-PYRAZOL-3-YLAMINE make it an interesting subject for further study in the field of organic chemistry. Researchers can explore its properties, reactions, and potential applications, leading to a deeper understanding of its role in chemical processes and the development of new compounds.
Used in Chemical Biology:
2-(3-CHLORO-PHENYL)-5-METHYL-2H-PYRAZOL-3-YLAMINE's potential interactions with biological systems make it a valuable subject for study in the field of chemical biology. By examining its interactions with proteins, enzymes, and other biomolecules, researchers can gain insights into its potential applications in drug discovery and the development of novel therapeutic agents.

InChI:InChI=1/C10H10ClN3/c1-7-5-10(12)14(13-7)9-4-2-3-8(11)6-9/h2-6H,12H2,1H3

Upstream product

• 1001-56-5 buta-2,3-dienenitrile 
• 14763-20-3 3-chlorophenyl hydrazine 
• 1118-61-2 3-Aminocrotononitrile 
• 2312-23-4 m-chlorophenylhydrazine hydrochloride 
• 2469-99-0 Cyanoaceton 
• 91587-54-1 Cyanaceton-(3-chlor-phenylhydrazon) 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 105438-65-1 5-Acetamido-1-(3-chlorophenyl)-3-methylpyrazole 
• 105438-66-2 N-[2-(3-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-benzamide 
• 124325-14-0 1-(3-Chlorophenyl)-3-methyl-5-benzylsulfonamidopyrazole 
• 81198-26-7 1-(3'-cloro)fenil-3-metil-4-nitroso-5-amminopirazolo 
• 124325-27-5 1-(3-Chlorophenyl)-3-methyl-4-nitroso-5-benzylsulfonamidopyrazole 
• 141497-80-5 1-(3-chlorophenyl)-3-methyl-4-amino-5-benzylsulphonamidopyrazole 
• 124325-26-4 1-(3-Chlorophenyl)-3-methyl-4-benzamido-5-aminopyrazole 
• 124325-23-1 3-phenyl-5-methyl-7-(3-chlorophenyl)-6,7-dihydropyrazolo<3,4-c><1,2,5>thiadiazine 2,2-dioxide 
• 1224944-49-3 5-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1260163-43-6 N-[1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1422773-43-0 6-amino-1-(3-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 
• 1422773-41-8 4-amino-1-(3-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 
• 1422773-40-7 2-[1-(3-chlorophenyl)-3-methyl-1H-5-pyrazolylaminomethylidene]malononitrile 

Relevant academic research and scientific papers

Phenoxydifluoromethyl substituted nitrogen heterocycles. Synthesis and heterocyclization reactions of ethyl 4,4-difluoro-4-phenoxyacetoacetate

Ethyl 4,4-difluoro-4-phenoxyacetoacetate was obtained and studied as a precursor to new heterocyclic compounds. 6-Hydroxypyrimidine, 1,3-dihydro-1,5-benzodiazepin-2-one, quinolin-2-one and 6-hydroxypyrazolo[3,4-b] pyridine derivatives containing phenoxydifluoromethyl groups were synthesized. These results make it possible to introduce aryloxydifluoromethyl substituents for the design of biologically active heterocycles.

Chiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of Pyrazole-Based Unnatural α-Amino Acid Derivatives

An enantioselective synthesis of unnatural pyrazole-based α-chiral amino acid derivatives from the asymmetric reaction of N-aryl-5-aminopyrazoles with β,γ-alkynyl-α-imino esters using a chiral spirocyclic phosphoric acid catalyst was developed. Using the established methodology, various pyrazole-based α-amino acid derivatives with tetrasubstituted carbon stereocenters were obtained in 67–98% yields and with 73–99% enantioselectivities. The NH2 functionality in the corresponding products enables further transformations to a chiral thiourea and a lactam. (Figure presented.).

One-pot three-component synthesis of a series of 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles in the presence of aluminum oxide as a nanocatalyst

[Figure not available: see fulltext.] One-pot three-component reaction of arylglyoxals, 3-aryl-3-oxopropanenitriles, and 5-amino-1-aryl-3-methylpyrazoles using various solvent systems and different catalysts under reflux conditions afforded the corresponding 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]- pyridine-5-carbonitrile derivatives. The best yields (70–91%) were obtained using Al2O3 as a nanocatalyst in H2O–EtOH, 1:1, under reflux conditions. The simplicity of workup procedure, the novelty of pyrazolopyridines, green solvent system, easy preparation of a nanocatalyst, and good to excellent yields of the products are the advantages of this synthetic strategy. The structures of all products were confirmed by FT-IR, 1H and13C NMR, and mass spectral data.

Hexahydrospiro-pyrazolo[3,4-b]pyridine-4,1′-pyrrolo[3,2,1-ij]quinolines Derived from 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

The tricyclic isatin, 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (1), reacts with a combination of an aryl cyanomethyl ketone 8 and a 5-amino-1-arylpyrazole 7 to generate spirocyclic products 9.

SMALL MOLECULE INHIBITORS OF MCL-1 AND USES THEREOF

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having pyrazolopyridine structure which function as inhibitors of Mcl-1 protein, and their use as therapeutics for the treatment of cancer and other diseases.

9H-PYRIMIDO[4,5-B]INDOLES AND RELATED ANALOGS AS BET BROMODOMAIN INHIBITORS

The present disclosure provides substituted 9H-pyrimido[4,5-b]indoles and 5H-pyrido[4,3-b]indoles and related analogs represented by Formula I: and the pharmaceutically acceptable salts, hydrates, and solvates thereof, wherein R1a, A, B1, B2, G, X1, Y1, Y2, and Y3 are as defined as set forth in the specification. The present disclosure is also directed to the use of compounds of Formula I to treat a condition or disorder responsive to inhibition of BET bromodomains. Compounds of the present disclosure are especially useful for treating cancer.

One-pot, telescoped synthesis of N-aryl-5-aminopyrazoles from anilines in environmentally benign conditions

An efficient synthetic approach to synthesize N-aryl-5-aminopyrazoles from anilines via a one-pot, telescoped reaction performed in entirely aqueous conditions has been developed. This protocol provides a rapid, convenient method to prepare N-aryl-5-aminopyrazoles, useful building blocks for the synthesis of several bicyclic nitrogen heterocycles, by avoiding the isolation of the toxic intermediate arylhydrazines and the use of a metallic reductant. The Royal Society of Chemistry 2014.

Approach to the library of fused pyridine-4-carboxylic acids by combes-type reaction of acyl pyruvates and electron-rich amino heterocycles

A library of fused pyridine-4-carboxylic acids (including pyrazolo[3,4-b]pyridines, isoxazolo[5,4-b]pyridines, furo[2,3-b]pyridines, thieno[2,3-b]pyridines, and pyrido[2,3-d]pyrimidines) was generated by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles followed by hydrolysis of the ester. The library members were also demonstrated to undergo the standard combinatorial transformations including amide coupling and esterification, as well as less common heterocyclizations to 1,2,4-triazoles and 1,2,4-oxadiazoles.

Discovery of new orally active phosphodiesterase (PDE4) inhibitors

A series of 4-anilinopyrazolopyridine derivatives were synthesized and biologically evaluated as inhibitors of phosphodiesterase (PDE4). Chemical modification of 3, a structurally new chemical lead that was found in our in-house library, was focused on 1- and 3-substituents. Full details of the discovery of a new orally active chemical lead 5 are presented. Structure-activity relationship data, pharmacological evaluation, and the subtype selectivity study are also presented.