34605-62-4

Usage

Structure

1H-Pyrazole-4-carboxylic acid, 5-amino-1,3-dimethyl-, ethyl ester

Type of compound

Ethyl ester derivative

Usage

Building block for the synthesis of biologically active molecules, precursor in pharmaceutical drug production, reagent in chemical reactions

Significance

Potential applications in drug development and materials science, of interest to researchers and chemists in various industries.

Upstream product

• 60-34-4 methylhydrazine 
• 35260-93-6 ethyl 2-cyano-3-ethoxybut-2-enoate 
• 22038-72-8 methyldiazene 
• 35260-93-6 ethyl (E)-2-cyano-3-ethoxy-but-2-enoate 
• 302-15-8 methylhydrazine sulfuric acid 
• 35260-93-6 ethyl 2-cyano-3-ethoxy-3-methylacrylate 

Downstream Products

• 93621-37-5 ethyl 5-chlorosulfonyl-1,3-dimethylpyrazole-4-carboxylate 
• 947238-76-8 5-amino-1,3-dimethyl-1H-pyrazole-4-carbohydrazide 
• 173312-53-3 5-[(2-Ethyl-5-methyl-4-nitro-2H-pyrazole-3-carbonyl)-amino]-1,3-dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS

The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)

Pyrazolo[3,4-d]pyrimidine derivatives containing a Schiff base moiety as potential antiviral agents

A series of pyrazolo[3,4-d]pyrimidine derivatives containing a Schiff base moiety were synthesized, characterised, and evaluated for their activity against tobacco mosaic virus (TMV). Biological assays indicated that several of the derivatives exhibited significant activity against TMV. In particularly, compounds 5y and 5aa displayed excellent inactivating activity against TMV, with half maximal effective concentration (EC50) values of 70.3 and 53.65 μg/mL, respectively, which were much better than that of ribavirin (150.45 μg/mL), and 5aa was superior to ningnanmycin (EC50 = 55.35 μg/mL). Interactions of compounds 5y and 5aa with TMV coat protein (TMV-CP) were investigated using microscale thermophoresis and molecular docking. Compounds 5y and 5aa displayed strong binding capability to TMV-CP with dissociation constant (Kd) values of 22.6 and 9.8 μM, respectively. These findings indicate that pyrazolo[3,4-d]pyrimidine derivatives containing a Schiff base may be potential antiviral agents.

A Michael Equilibration Model to Control Site Selectivity in the Condensation toward Aminopyrazoles

A Michael equilibration model is presented to provide for site-selective pyrazole condensations between alkoxyacrylonitriles and hydrazines. Both pyrazole isomers were accessed with high selectivity by employment of kinetically or thermodynamically controlled conditions. Substrate scope and identification of Michael intermediates, as well as competitive pathways, support the presented mechanistic proposal. Sandmeyer derivatization provided site-selective access to fully substituted pyrazoles.

Synthesis and herbicidal activities of a series of di(aminopyrazoly) ketone derivatives

(Chemical Equation Presented) In order to obtain new lead compounds with high herbicidal activity, a series of 5-amino pyrazole derivatives were designed and synthesized using a series of relational synthons. Their structures were determined by IR, 1H NMR, and elemental analyses. These compounds were screened for herbicidal activities against rape and barnyard grass. Their structure-activity relationships are discussed.

5-Aminopyrazoles from enolisable ketones and 1-cyano-1-alkylhydrazines

The reaction of enolisable ketones with 1-alkyl-1-cyanohydrazines leads to the corresponding cyanohydrazones. These compounds cyclise under thermal or mildly basic conditions, furnishing the corresponding 5-aminopyrazoles in good yield. In some cases, the hydrazones cannot be isolated, and the pyrazole derivatives are directly obtained. Hydrazone-enehydrazine tautomerism was observed, but no subsequent [3,3] rearrangement.

Synthesis of Pyrrazoles and Pyrazolopyrimidines from 3-Arylsulfonylaminoacrylates

3-Arylsulfonylaminopyrazole-4-carboxamides and -carboxylates were synthesized from 3-arylsulfonylamino-3-methylthiocyanoacrylate derivatives as potential herbicidal inhibitors of the enzyme acetohydroxyacetic acid synthase (AHAS). Some of these compounds