103259-35-4

Usage

Uses

Used in Research and Development:
Ethyl 5-amino-1H-pyrazole-4-carboxylate is used as a research chemical for the synthesis and study of various compounds and materials. Its unique structure and properties make it a valuable intermediate in the development of new chemical entities and pharmaceuticals.
Used in Pharmaceutical Industry:
Ethyl 5-amino-1H-pyrazole-4-carboxylate is used as a building block in the synthesis of potential drug candidates. Its presence in the molecular structure can contribute to the desired biological activity and therapeutic effects, making it a valuable component in the design of new medications.
Used in Chemical Synthesis:
Ethyl 5-amino-1H-pyrazole-4-carboxylate is used as a reagent in the synthesis of various organic compounds. Its versatility in chemical reactions allows for the creation of a wide range of products, from specialty chemicals to advanced materials.

Upstream product

• 42466-67-1 ethyl (ethoxymethylene)cyanoacetate 
• 64-17-5 ethanol 
• 7803-57-8 hydrazine hydrate 
• 94-05-3 2-cyano-3-ethoxyacrylic acid ethyl ester 
• 144918-37-6 (E)-ethyl 2-cyano-3-ethoxyacrylate 
• 6630-64-4 ethyl 2-cyano-3-morpholin-4-ylacrylate 
• 105-56-6 ethyl 2-cyanoacetate 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 

Downstream Products

• 104556-86-7 3-ethoxycarbonylpyrazolo<1,5-a>pyrimidin-7-one 
• 624720-40-7 3-amino-1-hydroxycarbamoylmethyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 78562-03-5 ethyl 7-(pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 41621-10-7 3-Amino-4-pyrazolecarboxylic Acid Hydrazide 
• 384835-91-0 ethyl 3-amino-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate 
• 1353100-91-0 ethyl 3-bromo-1H-pyrazole-4-carboxylate 
• 1372853-84-3 ethyl 3-benzyl-2-phenyl-5H-imidazo[1,2-b]pyrazole-7-carboxylate 
• 115703-22-5 3-chlorosulfonyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 1190060-37-7 (rac)-ethyl 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate 
• 1544457-95-5 ethyl 6-(2-hydroxybenzoyl)-7-isopropyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 90641-65-9 ethyl 5-amino-1-ethyl-1H-pyrazole-4-carboxylate 
• 90641-64-8 N₁-ethyl-3-amino-4-carboethoxypyrazole 
• 832741-06-7 ethyl 6-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 512825-94-4 ethyl 5-cyclopropyl-7-(difluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 

Relevant academic research and scientific papers

Fused 3-hydroxy-3-trifluoromethylpyrazoles inhibit mutant huntingtin toxicity

Here, we describe the selection and optimization of a chemical series active in both a full-length and a fragment-based Huntington's disease (HD) assay. Twenty-four thousand small molecules were screened in a phenotypic HD assay, identifying a series of compounds bearing a 3-hydroxy-3- trifluoromethylpyrazole moiety as able to revert the toxicity induced by full-length mutant Htt by up to 50%. A chemical exploration around the series led to the identification of compound 4f, which demonstrated to be active in a Htt171-82Q rat primary striatal neuron assay and a PC12-Exon-1 based assay. This compound was selected for testing in R6/2 mice, in which it was well-tolerated and showed a positive effect on body weight and a positive trend in preventing ventricular volume enlargment. These studies provide strong rationale for further testing the potential benefits of 3-hydroxy-3-trifluoromethylpyrazoles in treating HD.

Design and synthesis of Imidazo[1,2-b]pyridazine IRAK4 inhibitors for the treatment of mutant MYD88 L265P diffuse large B-cell lymphoma

Harboring MYD88 L265P mutation triggers tumors growth through the activation of NF-κB by interleukin-1 receptor associated kinase 4 (IRAK4) in diffuse large B-cell lymphoma (DLBCL), highlighting IRAK4 as a therapeutic target for tumors driven by aberrant MYD88 signaling. Herein, we report the design, synthesis, and structure?activity relationships of imidazo[1,2-b]pyridazines as potent IRAK4 inhibitors. The representative compound 5 exhibited excellent IRAK4 potency (IRAK4 IC50 = 1.3 nM) and favorable kinase selectivity profile. It demonstrated cellular selectivity for activated B cell–like (ABC) subtype DLBCL with MYD88 L265P mutation in cytotoxicity assay. The kinase inhibitory efficiency of compound 5 was further validated by Western blot analysis of phosphorylation of IRAK4 and downstream signaling in OCI-LY10 and TMD8 cells. Besides, combination of compound 5 and BTK inhibitor ibrutinib synergistically reduced the viability of TMD8 cells. These results indicated that compound 5 could be a promising IRAK4 inhibitor for the treatment of mutant MYD88 DLBCL.

MACROCYCLIC SULFONYLAMIDE DERIVATIVES USEFUL AS NLRP3 INHIBITORS

The present invention relates to macrocyclic compounds, such as macrocyclic sulfonyl amides. The present invention further relates to associated salts, solvates, prodrugs and pharmaceutical compositions, and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by NLRP3 inhibition.

Discovery and structure ? activity relationship exploration of pyrazolo[1,5-a]pyrimidine derivatives as potent FLT3-ITD inhibitors

Internal tandem duplications of FLT3 (FLT3-ITD) occur in approximately 25% of all acute myeloid leukemia (AML) cases and confer a poor prognosis. Optimization of the screening hit 1 from our in-house compound library led to the discovery of a series of pyrazolo[1,5-a]pyrimidine derivatives as potent and selective FLT3-ITD inhibitors. Compounds 17 and 19 displayed potent FLT3-ITD activities both with IC50 values of 0.4 nM and excellent antiproliferative activities against AML cell lines. Especially, compounds 17 and 19 inhibited the quizartinib resistance- conferring mutations, FLT3D835Y, both with IC50 values of 0.3 nM. Moreover, western blot analysis indicated that compounds 17 and 19 potently inhibited the phosphorylation of FLT3 and attenuated downstream signaling in AML cells. These results indicated that pyrazolo[1,5-a]pyrimidine derivatives could be promising FLT3-ITD inhibitors for the treatment AML.

A class of FLT3 kinase inhibitors, preparation and application thereof

The invention relates to a class of FLT3 kinase inhibitors, preparation and application thereof, wherein specifically the compound has a structure represented by a formula (I), and all groups and substituents are defined in the specification. The invention also discloses a preparation method of the compound, and application of the compound in inhibition of FLT3.

Synthetic method of pesticide intermediate pyrazole-4-ethyl formate

The invention discloses a synthetic method of pesticide intermediate pyrazole-4-ethyl formate. The method comprises the following steps: 1) ethyl cyanoacetate and triethyl orthoformate are placed in a flask, acetic anhydride is added for a reaction, an oil pump is used for performing underpressure distillation to obtain efhylene efhoxymethylene cyanoncetata; 2) efhylene efhoxymethylene cyanoncetata is dissolved in ethanol, hydrazine hydrate is added drop by drop, a solvent is used for underpressure distillation to obtain 3-amino-pyrazoles-4-ethyl formate; and 3) adding pyrazoles-4-ethyl formate and glacial acetic acid are added in a reaction bottle, hydrochloric acid is added drop by drop, a sodium nitrite solution is added drop by drop, after the reaction, ethanol is added for backflow and vacuum concentration, dichloromethane and water are added for stirring and layering, and an organic layer is re-crystallized to obtain the finished product. By employing ester condensation, cyclization and deamination reactions, the preparation technology is simple, and the product is easily purified, production cost is low, and the method is suitable for large-scale industrial production.

Discovery of tetrahydropyrazolopyrimidine carboxamide derivatives as potent and orally active antitubercular agents

Tetrahydropyrazolo[1,5-a]pyrimidine scaffold was identified as a hit series from a Mycobacterium tuberculosis (Mtb) whole cell high through-put screening (HTS) campaign. A series of derivatives of this class were synthesized to evaluate their structure-activity relationship (SAR) and structure-property relationship (SPR). Compound 9 had a promising in vivo DMPK profile in mouse and exhibited potent in vivo activity in a mouse efficacy model, achieving a reduction of 3.5 log CFU of Mtb after oral administration to infected mice once a day at 100 mg/kg for 28 days. Thus, compound 9 is a potential candidate for inclusion in combination therapies for both drug-sensitive and drug-resistant TB.

Application of Ullmann and Ullmann-Finkelstein reactions for the synthesis of N-aryl-N-(1H-pyrazol-3-yl) acetamide or N-(1-aryl-1H-pyrazol-3-yl) acetamide derivatives and pharmacological evaluation

Ullmann-type reactions are becoming a major tool in medicinal chemistry. In this article, we describe the use of these Copper-catalyzed reactions with various precursors, acyl-heteroarylamines or pyrazoles of interest for pharmacomodulation. To the medicinal chemist they offer new, usually untapped disconnection approaches to compounds of interest. They thus open the way to new original analogues of bioactive compounds possibly not patented, from common building-blocks. They also allow C to N bioisosteric replacements, which sometimes are synthetically challenging. We report for the first time the critical effect of acetylamino substituents on the regioselective arylation of unsymmetrical pyrazoles that are useful for medicinal chemists. Finally, we have applied this strategy to the design of novel AT1 receptor antagonists. Though this family has been extensively investigated in the past 30 years, N-arylation and C to N replacement made possible by Ullmann chemistry, can produce original antagonists.

PROCESS FOR THE PREPARATION OF A PYRAZOLE DERIVATIVE

Disclosed here is a process for the preparation of 3 - amino pyrazole derivative of Formula (I) where R1 = H, C1 - C4 alkyl group or benzyl group or phenyl group; R2 = C1 - C6 alkyl group or benzyl group; comprising a step of reacting the compound of Formula (Ill) with hydrazine hydrate.

Synthesis of 3-substituted-1-methyl-1H-thieno[2,3-c]pyrazoles

We report a simple and practical six-step synthesis of new 1-methyl-1H-thieno[2,3-c]pyrazoles from 3-amino-1H-pyrazole-4-carboxylic acid ethyl ester. Copyright Taylor & Francis Group, LLC.