40401-39-6

Usage

Uses

Used in Scientific Research:
CPP is used as a psychostimulant in scientific research for studying the effects of psychostimulants on the central nervous system. Its unique chemical structure allows researchers to investigate the mechanisms of action and potential therapeutic benefits of psychostimulant compounds.
Used in Neurological Disorder Treatment:
CPP is being investigated for its potential therapeutic applications in the treatment of various neurological disorders. Its psychostimulant properties may offer benefits in managing symptoms and improving the quality of life for patients with these conditions.
Used in Drug Development:
As a chemical compound with unique properties, CPP has been studied for its potential role in drug development. Its structure and activity may provide insights into the design of new drugs with improved efficacy and safety profiles.
Used as a Therapeutic Target:
CPP is also being explored as a potential therapeutic target for certain diseases. Its interaction with specific biological pathways and receptors may offer opportunities for the development of targeted therapies that can modulate disease progression and improve patient outcomes.

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

Upstream product

• 1118-61-2 3-Aminocrotononitrile 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 106-47-8 4-chloro-aniline 
• 2469-99-0 Cyanoaceton 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 14763-20-3 3-chlorophenyl hydrazine 

Downstream Products

• 77746-58-8 N'-[2-(4-Chloro-phenyl)-4-formyl-5-methyl-2H-pyrazol-3-yl]-N,N-dimethyl-formamidine 
• 86817-21-2 2-(4-Chloro-phenyl)-5-methyl-4-thiocyanato-2H-pyrazol-3-ylamine 
• 129139-76-0 N-[2-(4-Chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-C-phenyl-methanesulfonamide 
• 81314-61-6 1-(4'-cloro)fenil-3-metil-4-nitroso-5-amminopirazolo 
• 1575698-82-6 1-(4-chlorophenyl)-5-ethyl-3-methyl-4-phenyl-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 1575698-85-9 1-(4-chlorophenyl)-5-ethyl-4-(4-methoxyphenyl)-3-methyl-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 1575698-80-4 5-butyl-1-(4-chlorophenyl)-3-methyl-4-phenyl-1,4,5,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 105438-94-6 5-Benzylamino-1-(4-chlorophenyl)-3-methyl-4-nitrosopyrazole 
• 105438-52-6 1-(4-Chloro-phenyl)-3-methyl-5-phenyl-1,6-dihydro-imidazo[4,5-c]pyrazole 
• 105438-79-7 5-(benzylamino)-1-(4-chlorophenyl)-3-methyl-1H-pyrazole 
• 105438-93-5 1-(4-Chlorophenyl)-5-ethylamino-3-methyl-4-nitrosopyrazole 

Relevant academic research and scientific papers

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.).

Oxidative Ring-Opening of 1H-Pyrazol-5-amines and Its Application in Constructing Pyrazolo–Pyrrolo–Pyrazine Scaffolds by Domino Cyclization

Herein, an oxidative ring-opening of 1H-pyrazol-5-amines to form 3-diazenylacrylonitrile derivatives under mild and transition-metal-free conditions is described. In addition, the nucleophilic addition of deprotonated 1H-pyrrole-2-carbaldehydes to the vinyl moiety of the yielded 3-diazenylacrylonitriles could trigger domino cyclization to afford the 3H-pyrazolo[3,4-e]pyrrolo[1,2-a]pyrazine derivatives. Computational studies suggest that the oxidation of 1H-pyrazol-5-amines in the presence of PhIO is through the formation of a hydroxylamine intermediate followed by elimination of H2O to result in the ring-opening product. The detailed domino cyclization pathway leading to the pyrazolo–pyrrolo–pyrazine scaffolds is revealed.

Microwave synthesis of 1-aryl-1H-pyrazole-5-amines

A microwave-mediated synthesis of 1H-pyrazole-5-amines utilizing 1 M HCl at 150 °C was developed in order to provide products in a matter of minutes with minimal purification. Most reactions are complete in only 10 min and can be isolated via a simple filtration without the need for further purification by column chromatography or recrystallization. This method tolerates a range of functional groups and can be performed on milligram to gram scales.

Efficient catalyst-free tricomponent synthesis of new spiro[cyclohexane-1,4′-pyrazolo[3,4-e][1, 4]thiazepin]-7′(6′H)-ones

A series of spirocyclohexane-1,4′-pyrazolothiazepinones were synthesized by one-pot multicomponent cyclocondensation reactions between 5-amino-1-arylpyrazoles, cyclohexanone and mercaptoacetic acid with good yields and easy purification protocols. Some control experiments involving isolation of reaction intermediates were performed leading to the proposal of three alternative mechanistic pathways conducting to the named spiroheterocycles. All target molecules were fully characterized by IR, NMR, melting point and HRMS.

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.

Application of 5-aminopyrazole compounds to plant growth regulation aspect

The invention discloses application of 5-aminopyrazole compounds to plant growth regulation aspect in the technical field of pesticide compounds, in particular to application of the 5-aminopyrazole compounds shown by the formula to the plant growth regulation aspect, particularly the application to the plant growth inhibition. The formula I is shown in the description. The compound shown in the formula I can be used as a weedicide; weeds in places such as highway and railway can be killed through regulating the concentration of the 5-aminopyrazole compounds, wherein the R1 is hydrogen or alkylor phenyl or substituted phenyl; R2 is alkyl; R3 is hydrogen or halogen.

Multicomponent Dipolar Cycloaddition Strategy: Combinatorial Synthesis of Novel Spiro-Tethered Pyrazolo[3,4-b]quinoline Hybrid Heterocycles

The stereoselective syntheses of a library of novel spiro-tethered pyrazolo[3,4-b]quinoline-pyrrolidine/pyrrolothiazole/indolizine-oxindole/acenaphthene hybrid heterocycles have been achieved through the 1,3-dipolar cycloaddition of azomethine ylides generated in situ from α-amino acids and 1,2-diketones to dipolarophiles derived from pyrazolo[3,4-b]quinoline derivatives.

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.

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.

VILSMEIER-HAACK REACTION OF 5-AMINO- AND 5-ACYLAMINO-PYRAZOLES

The Vilsmeier-Haack reaction of 5-aminopyrazole derivatives 1 was investigated in view of contradictory literature reports.Structure 2 of the products was proved both chemically and spectroscopically.The mechanism of the reaction was postulated on the basis of isolated intermediates 7 and 8. 5-Acylaminopyrazoles 9, 10 and 11 were found to give also 2 (and 7) under the Vilsmeier conditions by an acyl splitting reaction, proceeding probably via diacylamino derivatives 12.Compounds 2 provided a simple route to pyrazolopyrimidine derivatives 13 and 14 as well as to azomethine compounds 15-18.