81153-64-2

Usage

Uses

Used in Organic Synthesis:
5-Methyl-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester is used as a key intermediate in organic synthesis for the preparation of various chemical compounds. Its unique structure allows for versatile reactions, facilitating the creation of a wide array of molecules with potential applications in different fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-Methyl-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester is employed as a precursor in the development of new drugs and active pharmaceutical ingredients. Its role in the synthesis of medicinal compounds is vital, as it can be modified to produce a range of therapeutic agents with specific pharmacological properties.
Used in Drug Production:
5-Methyl-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester is utilized in the production of various drugs, contributing to the formulation of active pharmaceutical ingredients. Its presence in the synthesis process is essential for creating effective medications that address a multitude of health conditions.

InChI:InChI=1/C13H14N2O2/c1-3-17-13(16)12-9-10(2)15(14-12)11-7-5-4-6-8-11/h4-9H,3H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 59-88-1 phenylhydrazine hydrochloride 
• 135351-18-7 (E)-1,1,1-trichloro-4-methoxypent-3-en-2-one 
• 907178-33-0 (E)-2-(N-methoxy-N-methyl-amino)-4-oxo-2-pentenoic acid ethyl ester 
• 100-63-0 phenylhydrazine 
• 135351-18-7 1,1,1-trichloro-4-methoxy-3-penten-2-one 
• 103-03-7 1-phenylsemicarbazide 
• 62-53-3 aniline 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 28663-68-5 ethyl chloro(2-phenylhydrazono)acetate 
• 615-79-2 ethyl 2,4-diketopentanoate 
• 126580-18-5 ethyl 2-diazo-3-hydroxy-4-phenylpentanoate 
• 623-47-2 propynoic acid ethyl ester 
• 98790-58-0 ethyl (Z)-4-hydroxy-2-oxopent-3-enoate 

Downstream Products

• 10199-57-2 5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid 
• 6831-91-0 5-methyl-1-phenylpyrazole 
• 103038-19-3 4-(5-methyl-4-nitro-pyrazol-1-yl)-aniline 
• 103753-92-0 5-methyl-4-nitro-1-(4-nitro-phenyl)-1H-pyrazole 
• 582297-95-8 CH₃O₄S^(1-)*C₁₄H₁₇N₂O₂⁽¹⁺⁾ 
• 32464-78-1 5-methyl-1-phenylpyrazole-3-carbaldehyde 
• 81153-60-8 6-[m-(5-Methyl-1-phenylpyrazole-3-carboxamido)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole 

Relevant academic research and scientific papers

Novel phenylpyrazole derivative and application thereof in medicine for reducing blood sugar

The invention belongs to the field of drug synthesis, and particularly relates to a phenyl pyrazole derivative and a preparation method thereof, and an application thereof in a hypoglycemic drug. The invention provides a novel phenylpyrazole derivative and a general formula thereof. In addition, the invention also provides a preparation method of the derivative and an application of the derivative in hypoglycemic drugs.

Benzopyrazolo ring derivative and application thereof in antitumor drugs

The invention belongs to the technical field of medicines, and provides a benzopyrazolo ring derivative as shown in a general formula and a preparation method thereof. The invention further disclosesthe benzene bipyrazolo ring derivative which can inhibit

Phenyl-1H-pyrazole derivative and application thereof in antitumor drugs

The invention belongs to the technical field of medicines, and provides a phenyl-1H-pyrazole derivative shown as a general formula and a preparation method thereof. The invention also discloses that the phenyl-1H-pyrazole derivative can inhibit the mutual combination of a programmed cell death receptor 1/a programmed cell death ligand 1 (PD-1/PD-L1) and can be used for preparing a PD-1/PD-L1 inhibitor.

Pyrazole-4-Carboxamide (YW2065): A Therapeutic Candidate for Colorectal Cancer via Dual Activities of Wnt/β-Catenin Signaling Inhibition and AMP-Activated Protein Kinase (AMPK) Activation

Dysregulation of the Wnt/β-catenin signaling pathway has been widely recognized as a pathogenic mechanism for colorectal cancer (CRC). Although numerous Wnt inhibitors have been developed, they commonly suffer from toxicity and unintended effects. Moreover, concerns have been raised in targeting this pathway because of its critical roles in maintaining stem cells and regenerating tissues and organs. On the basis of the anthelmintic drug pyrvinium and previous lead FX1128, we have developed a compound YW2065 (1c) which demonstrated excellent anti-CRC effects in vitro and in vivo. YW2065 achieves its inhibitory activity for Wnt signaling by stabilizing Axin-1, a scaffolding protein that regulates proteasome degradation of β-catenin. Simultaneously, YW2065 also led to the activation of the tumor suppressor AMPK, providing an additional anticancer mechanism. In addition, YW2065 showed favorable pharmacokinetic properties without obvious toxicity. The anti-CRC effect of YW2065 was highlighted by its promising efficacy in a mice xenograft model.

Discovery of 2-phenylthiazole-4-carboxylic acid, a novel and potent scaffold as xanthine oxidase inhibitors

The xanthine oxidase (XO) plays an important role in producing uric acid, and therefore XO inhibitors are considered as one of the promising therapies for hyperuricemia and gout. We have previously reported a series of XO inhibitors with pyrazole scaffold to extend the chemical space of current XO inhibitors. Herein, we describe further structural optimization to explore the optimal heterocycle by replacing the thiazole ring of Febuxostat with 5 heterocycle scaffolds unexplored in this field. All of these efforts resulted in the identification of compound 8, a potent XO inhibitor (IC50 = 48.6 nM) with novel 2-phenylthiazole-4-carboxylic acid scaffold. Moreover, lead compound 8 exhibited hypouricemic effect in potassium oxonate-hypoxanthine-induced hyperuricemic mice. These results promote the understanding of ligand-receptor interaction and might help to design more promising XO inhibitors.

Hydroxamic Acid-Based Histone Deacetylase (HDAC) inhibitors bearing a pyrazole scaffold and a cinnamoyl linker

Genetic abnormalities have been conventionally considered as hallmarks of cancer. However, recent studies have demonstrated that epigenetic mechanisms are also implicated in the insurgence and development of cancer. Patterns of the epigenetic component in

Biphenyl heterocyclic derivatives, their preparation and their use as medicaments (by machine translation)

The present invention relates to a novel biphenyl heterocyclic derivative represented by a general formula (I) and a preparation method thereof and use of a pharmaceutical composition containing the derivative for preparation of a drug for treating diabetes. The biphenyl heterocyclic derivative has extremely excellent hypoglycemic activity in vivo, and excellent in vivo safety and low liver toxicity risk of the compound having such a structure are unexpectedly found, and the novel biphenyl heterocyclic derivative may be used for preventing or treating diabetes.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

Synthesis, nematicidal activity and docking study of novel chromone derivatives containing substituted pyrazole

A series of chromone derivatives containing substituted pyrazole were designed and synthesized. Preliminary bioassays showed that most of the synthesized compounds exhibited good nematicidal activity in vivo against Meloidogyne incognita at 10 mg/L. Among the tested compounds, A10 and A11 exhibited 100% inhibition rates. In addition, the molecular docking results indicated that both compound A10 and A11 interacts with amino acid residue Tyr121, Trp279, Tyr70, Trp84 and Phe330 of AChE via hydrogen bond and π–π stacking. This investigation suggested that the chromone containing substituted pyrazole scaffold could be further optimized to explore novel, high-bioactivity nematicidal leads.

Design, synthesis, and biological evaluation of N,N-disubstituted-4-arylthiazole-2-methylamine derivatives as cholesteryl ester transfer inhibitors

Cholesteryl ester transfer protein (CETP) has been identified as a potential target for cardiovascular disease (CVD) for its important role in the reverse cholesteryl transfer (RCT) process. In our previous work, compound 5 was discovered as a moderate CETP inhibitor. The replacement of the amide linker by heterocyclic aromatics and then a series of N,N-substituted-4-arylthiazole-2-methylamine derivatives were designed by utilizing a conformational restriction strategy. Thirty-six compounds were synthesized and evaluated for their CETP inhibitory activities. Structure-activity relationship studies indicate that electron donor groups substituted ring A, and electron-withdrawing groups at the 4-position of ring B were critical for potency. Among these compounds, compound 30 exhibited excellent CETP inhibitory activity (IC50 = 0.79 ± 0.02 μM) in vitro and showed an acceptable metabolic stability.