14678-87-6

Basic information

• Product Name: 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: ETHYL 5-AMINO-1-(4-CHLOROPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE;BUTTPARK 19\09-71;AKOS BBS-00004494;5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;SALOR-INT L251445-1EA;5-amino-1-(4-chlorophenyl)-4-pyrazolecarboxylic acid ethyl ester;5-amino-1-(4-chlorophenyl)pyrazole-4-carboxylic acid ethyl ester
• CAS NO: 14678-87-6
• Molecular Formula: C₁₂H₁₂ClN₃O₂
• Molecular Weight: 265.7
• Mol File: 14678-87-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 408.4 °C at 760 mmHg
• Flash Point: 200.8 °C
• Appearance: /
• Density: 1.37 g/cm³
• Vapor Pressure: 7.01E-07mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(14678-87-6)
• EPA Substance Registry System: 5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(14678-87-6)

Safety Data

• Hazardous Substances Data: 14678-87-6(Hazardous Substances Data)

Usage

General Description

5-AMINO-1-(4-CHLORO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is a chemical compound with a molecular formula C12H11ClN4O2. It is an ethyl ester derivative of 5-amino-4-carboxypyrazole, which is a pyrazole-based building block commonly used in the synthesis of pharmaceuticals and agrochemicals. The compound contains an amino group, a chloro-phenyl group, and a carboxylic acid ester group, making it suitable for various organic synthetic applications. Its use in drug discovery and chemical research makes it an important intermediate in the development of biologically active compounds.

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

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

Downstream Products

• 116834-06-1 1-(4-Chloro-phenyl)-5-pyrrol-1-yl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 110821-33-5 ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate 
• 110821-36-8 ethyl 5-chloro-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate 
• 110821-40-4 5-Bromo-1-(4-chloro-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester 
• 110821-43-7 1-(4-Chloro-phenyl)-5-iodo-1H-pyrazole-4-carboxylic acid ethyl ester 
• 116834-13-0 4-Chloromethyl-1-(4-chloro-phenyl)-5-pyrrol-1-yl-1H-pyrazole 
• 116834-11-8 [1-(4-Chloro-phenyl)-5-pyrrol-1-yl-1H-pyrazol-4-yl]-methanol 
• 116834-09-4 1-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carboxylic acid 
• 116834-15-2 2-[1-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]acetonitrile 
• 116834-18-5 [1-(4-Chloro-phenyl)-5-pyrrol-1-yl-1H-pyrazol-4-yl]-acetic acid 
• 116834-28-7 2-[1-(4-Chloro-phenyl)-5-pyrrol-1-yl-1H-pyrazol-4-yl]-propionic acid 
• 116834-22-1 [1-(4-Chloro-phenyl)-5-pyrrol-1-yl-1H-pyrazol-4-yl]-cyano-acetic acid ethyl ester 
• 116834-25-4 [1-(4-Chloro-phenyl)-5-pyrrol-1-yl-1H-pyrazol-4-yl]-cyano-methyl-acetic acid ethyl ester 
• 1349199-07-0 1-(4-chlorophenyl)-6-methylpyrazolo[3,4-d][1,3]oxazin-4(1H)-one 

Relevant articles and documents

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.

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.