14678-87-6

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form biologically active compounds. Its unique structure allows for the creation of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is utilized as a building block in the development of agrochemicals, such as pesticides and herbicides. Its chemical properties enable the design of novel compounds with improved efficacy and selectivity in controlling pests and weeds.
Used in Organic Synthesis:
5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is employed as a versatile reagent in organic synthesis, allowing for the formation of a wide range of chemical compounds. Its functional groups facilitate various chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Drug Discovery:
As a crucial intermediate in drug discovery, 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is used for the development of new pharmaceutical agents. Its unique structure and functional groups contribute to the design and synthesis of potential drug candidates with novel mechanisms of action and therapeutic potential.
Used in Chemical Research:
In the field of chemical research, 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER serves as an important compound for studying various chemical reactions and mechanisms. Its presence in different chemical systems allows researchers to explore its reactivity, stability, and potential applications in various chemical processes.

InChI:InChI=1/C12H12ClN3O2/c1-2-18-12(17)10-7-15-16(11(10)14)9-5-3-8(13)4-6-9/h3-7H,2,14H2,1H3

Upstream product

• 68350-76-5 2-cyano-3-methoxyacrylic acid ethyl ester 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 144918-37-6 (E)-ethyl 2-cyano-3-ethoxyacrylate 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 72459-84-8 ethyl (ethoxymethylene)cyanoacetate 
• 42466-67-1 ethyl (ethoxymethylene)cyanoacetate 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 

Downstream Products

• 5334-29-2 1-(p-chlorophenyl)pyrazolo<3,4-d>pyrimidin-4(5H)-one 
• 5334-59-8 4-chloro-1-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine 

Relevant academic research and scientific papers

Novel Pyrazolo[3,4- d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation

Plant pathogenic fungi seriously threaten agricultural production. There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound g22 exhibited remarkable antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.25 mg/L, close to that of commercial fungicide boscalid (EC50 = 0.96 mg/L) and fluopyram (EC50 = 1.91 mg/L). Moreover, compound g22 possessed prominent protective activity against S. sclerotiorum in vivo for 24 h (95.23%) and 48 h (93.78%), comparable to positive control boscalid (24 h (96.63%); 48 h (93.23%)). Subsequent studies indicated that compound g22 may impede the growth and reproduction of S. sclerotiorum by affecting the morphology of mycelium, destroying cell membrane integrity, and increasing cell membrane permeability. In addition, the application of compound g22 did not injure the growth or reproduction of Italian bees. This study revealed that compound g22 is expected to be developed for efficient and safe agricultural fungicides.

Synthesis of pyrazole-carboxamides and pyrazole-carboxylic acids derivatives: Simple methods to access powerful building blocks

Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.

Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity

The identification of novel Topoisomerase II (Topo II) inhibitors is one of the most attractive directions in the field of bactericide research and development. In our ongoing efforts to pursue the class of inhibitors, six series of 70 novel coumarin-pyrazole carboxamide derivatives were designed and synthesized. As a result of the evaluation against four destructive bacteria, including Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8III-k (MIC = 0.25 mg/L) showed considerable inhibitory activity than ciprofloxacin (MIC = 0.5 mg/L) against Escherichia coli and 8V-c (MIC = 0.05 mg/L) exhibited excellent antibacterial activity than ciprofloxacin (MIC = 0.25 mg/L) against Salmonella. The selected compounds (8III-k, 8V-c and 8V-k) exhibit potent inhibition against Topo II and Topo IV with IC50 values (9.4–25 mg/L). Molecular docking model showed that the compounds 8V-c and 8V-k can bind well to the target by interacting with amino acid residues. It will provide some valuable information for the commercial Topo II inhibiting bactericides.

Targeting Pim Kinases and DAPK3 to Control Hypertension

Sustained vascular smooth muscle hypercontractility promotes hypertension and cardiovascular disease. The etiology of hypercontractility is not completely understood. New therapeutic targets remain vitally important for drug discovery. Here we report that Pim kinases, in combination with DAPK3, regulate contractility and control hypertension. Using a co-crystal structure of lead molecule (HS38) in complex with DAPK3, a dual Pim/DAPK3 inhibitor (HS56) and selective DAPK3 inhibitors (HS94 and HS148) were developed to provide mechanistic insight into the polypharmacology of hypertension. In vitro and ex vivo studies indicated that Pim kinases directly phosphorylate smooth muscle targets and that Pim/DAPK3 inhibition, unlike selective DAPK3 inhibition, significantly reduces contractility. In vivo, HS56 decreased blood pressure in spontaneously hypertensive mice in a dose-dependent manner without affecting heart rate. These findings suggest including Pim kinase inhibition within a multi-target engagement strategy for hypertension management. HS56 represents a significant step in the development of molecularly targeted antihypertensive medications. Carlson et al. use crystal structure-guided medicinal chemistry techniques to develop a dual Pim/DAPK3 inhibitor (HS56) that reduces myosin phosphorylation and contractility in smooth muscle. Their findings reveal the contribution of Pim kinases to the pathology of hypertension, suggesting a novel multi-target engagement strategy for molecularly targeted antihypertensive medications.

Lead optimization of spiropyrazolopyridones: A new and potent class of dengue virus inhibitors

Spiropyrazolopyridone 1 was identified, as a novel dengue virus (DENV) inhibitor, from a DENV serotype 2 (DENV-2) high-throughput phenotypic screen. As a general trend within this chemical class, chiral resolution of the racemate revealed that R enantiomer was significantly more potent than the S. Cell-based lead optimization of the spiropyrazolopyridones focusing on improving the physicochemical properties is described. As a result, an optimal compound 14a, with balanced in vitro potency and pharmacokinetic profile, achieved about 1.9 log viremia reduction at 3 × 50 mg/kg (bid) or 3 × 100 mg/kg (QD) oral doses in the dengue in vivo mouse efficacy model.

Synthesis of 3H-pyrazolo[3,4-c]isoquinolines and thieno[3,2-c]isoquinolines via cascade imination/intramolecular decarboxylative coupling

A general approach for the synthesis of 3H-pyrazolo[3,4-c]isoquinolines and thieno[3,2-c]isoquinolines is described involving the implementation of a cascade imination/intramolecular decarboxylative coupling between potassium 2-amino(hetero)benzoates and 2-haloarylaldehydes. The reactions of pyrazole-based substrates require a Pd-Cu bimetallic system for superior yields whereas the thienyl-based substrates afford the products in excellent yields with a Pd-catalyst only.

NOVEL COMPOUNDS AS AGONIST FOR PPAR GAMMA AND PPAR ALPHA, METHOD FOR PREPARATION OF THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME

The present invention relates to novel compounds accelerating the activity of Peroxisome proliferator-activated receptor gamma (PPARγ) and alpha (PPARα), processes of preparing the same, and pharmaceutical compositions containing the same as an active agent.

A clean and rapid synthesis of 5-aminopyrazole-4-carboxylic acid esters and nitriles using montmorillonite K10

A series of 5-aminopyrazole-4-carboxylates (4a-f) and nitriles (5a-f) have been synthesized under heterogeneous catalytic conditions using montmorillonite.