16078-71-0

Basic information

• Product Name: 5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE
• Synonyms: 1H-Pyrazole-4-carboxylic acid, 5-amino-1-phenyl-, ethyl ester;5-amino-1-phenyl-1h-pyrazole-4-carboxylicaciethylester;AKOS B000506;AKOS 231-01;AKOS NCG-0076;AKOS BBS-00002940;3-AMINO-4-CARBETHOXY-2-PHENYLPYRAZOLE;5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE
• CAS NO: 16078-71-0
• Molecular Formula: C₁₂H₁₃N₃O₂
• Molecular Weight: 231.25
• EINECS: 240-224-8
• Product Categories: Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Pyrazoles
• Mol File: 16078-71-0.mol
• Article Data: 34

Chemical Properties

• Melting Point: 98-100 °C(lit.)
• Boiling Point: 373.33°C (rough estimate)
• Flash Point: 186.693 °C
• Appearance: white to light yellow crystalline flakes
• Density: 1.1818 (rough estimate)
• Vapor Pressure: 3.9E-06mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: methanol: soluble25mg/mL, clear, colorless
• PKA: 0.55±0.10(Predicted)
• BRN: 211079
• CAS DataBase Reference: 5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE(16078-71-0)
• EPA Substance Registry System: 5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE(16078-71-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39-36/37/39
• WGK Germany: 3
• RTECS: UQ6392025
• Hazardous Substances Data: 16078-71-0(Hazardous Substances Data)

Usage

Uses

Ethyl 5-amino-1-phenyl-4-pyrazolecarboxylate may be used as internal standard for the GC-MS determination of etomidate [ethyl-1-(1-phenylethyl)-1H-imidazole-5-carboxylate] in mouse brain tissue.

General Description

Ethyl 5-amino-1-phenyl-4-pyrazolecarboxylate is a heterocyclic building block.

InChI:InChI=1/C12H13N3O2/c1-2-17-12(16)10-8-14-15(11(10)13)9-6-4-3-5-7-9/h3-8H,2,13H2,1H3

Upstream product

• 100-63-0 phenylhydrazine 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 
• 105-56-6 ethyl 2-cyanoacetate 
• 144918-37-6 (E)-ethyl 2-cyano-3-ethoxyacrylate 
• 59-88-1 phenylhydrazine hydrochloride 
• 42466-67-1 ethyl (ethoxymethylene)cyanoacetate 
• 62-53-3 aniline 
• 591-50-4 iodobenzene 
• 6994-25-8 3-amino-4-pyrazolecarboxylic acid ethyl ester 
• 68350-76-5 2-cyano-3-methoxyacrylic acid ethyl ester 
• 94-05-3 2-cyano-3-ethoxyacrylic acid ethyl ester 
• 72459-84-8 ethyl (ethoxymethylene)cyanoacetate 

Downstream Products

• 635324-67-3 ethyl 4-chloro-6-[3-(trifluoromethyl)phenyl]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 203123-14-2 5-(Methanesulfonyl-methyl-amino)-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 203123-08-4 5-Methanesulfonylamino-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 716379-14-5 5-amino-4-benzyloxycarbonylamino-1-phenylpyrazole 
• 85561-52-0 1-phenyl-4,5-diaminopyrazole 
• 98946-22-6 5-amino-1-phenyl-1H-pyrazole-4-carbonyl azide 
• 94692-06-5 1-phenyl-5-(pyrrol-1-yl)-1H-pyrazole-4-carbohydrazide 
• 1159591-70-4 4,4'-bis(6,7-dihydro-1-phenyl-4-oxo-6-thioxo-1H,5H-pyrazolo[3,4-d]-pyrimidin-5-yl)-1,1'-diphenylsulfone 
• 1159591-71-5 4,4'-bis(3-(4-ethyloxy-1-phenyl-1H-pyrazol-5-yl)thioureido)-1,1'-diphenylsulfone 

Relevant articles and documents

Design, synthesis and anti-P. falciparum activity of pyrazolopyridine–sulfonamide derivatives

Ten 1-phenyl-1H-pyrazolo[3,4-b]pyridine derivatives connected by a linker group to benzenesulfonamide moieties with different substituents in the 4-position were synthesized and assayed against Plasmodium falciparum. These ten compounds exhibited activity in vitro against the chloroquine-resistant clone W2 with IC50values ranging from 3.46 to 9.30 μM. The most active derivatives with substituent R2= Cl or CH3at the benzenesulfonamide moiety exhibited the lowest IC50. Compounds with an R1= CO2Et substituent at the 5-position of the 1H-pyrazolo[3,4-b]pyridine ring presented lower activity than those with a CN substituent. The 1H-pyrazolo[3,4-b]pyridine system appears to be promising for further studies as an antimalarial for overcoming the burden of resistance in P. falciparum.

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.

COMPOUNDS HAVING PDE9A INHIBITORY ACTIVITY, AND PHARMACEUTICAL USES THEREOF

The present invention provides a compound having a specific chemical structure and having PDE9A inhibitory activity, or a pharmaceutically acceptable salt thereof. The present invention provides a composition containing the compound or a pharmaceutically acceptable salt thereof. The present invention provides a pharmaceutical use, for treating or preventing PDE9A-related diseases, of the compound according to the present invention, a salt thereof, and a composition containing the compound or salt. The present invention also provides a method for treating or preventing PDE9A-related diseases, the method comprising administering an effective amount of the compound according to the present invention, a salt thereof, or a composition containing the compound or salt to a subject in need of treatment.

New 1,2,4-triazole/pyrazole hybrids linked to oxime moiety as nitric oxide donor celecoxib analogs: Synthesis, cyclooxygenase inhibition anti-inflammatory, ulcerogenicity, anti-proliferative activities, apoptosis, molecular modeling and nitric oxide release studies

Two new series of hybrid structures 16a-f and 19a-f containing 1,2,4-triazole moiety, pyrazole core with COX-2 pharmacophore and oxime as NO donor moiety were designed, synthesized and evaluated for anti-inflammatory, cytotoxic activities and NO release. All compounds were more selective for COX-2 isozyme especially the sulphamoyl derivatives (16b, 16e, 19b and 19e) had COX-2 selectivity indexes (S.I. = 9.78, 8.57, 10.78 and 10.47 respectively) in comparison to celecoxib (S.I. = 8.68). Similarly, 16b, 16e, 19b and 19e were the most potent anti-inflammatory derivatives with ED50 = 46.98–54.45 μmol/kg better than celecoxib (ED50 = 76.09 μmol/kg). Also, 16b, 16e, 19b and 19e were significantly less ulcerogenic (ulcer indexes = 2.79–3.95) upon comparison with ibuprofen (ulcer index = 20.25) and comparable with celecoxib (ulcer index = 2.93). Regarding anti-cancer activity, most of the target derivatives 16a-f and 19a-f showed good activities against A-549, MCF-7, HCT-116 and PC-3 cancer cell lines. Additionally, these derivatives examined against F180 fibroblasts to investigate their selectivity indexes. The sulphamoyl derivatives with internal oxime 19b and 19e were the most potent derivatives against all used cell lines especially PC-3 (IC50 = 1.48 and 0.33 μM respectively) with 11.75 and 39.4-fold respectively selectivity towards PC-3 than F180 fibroblasts. The mechanistic investigation of 19b and 19e revealed that both compounds arrested cell cycle at G2/M phase by 32.16 and 39.95 folds, up-regulated Bax expression by 6.83 and 14.52 folds and down-regulated the expression of the gene Bcl-2 by 0.57 and 0.36fold respectively. Also, 19b and 19e were good inhibitor for p38MAPK (0.65 for 19b and 0.58 for 19e) and VEGFR-2 (0.39 for 19b and 0.54 for 19e) in comparison with PC-3 control cell. All compounds 16a-f and 19a-f released NO in a slow rate (0.15–3.17%) and the four sulphamoyl derivatives 16b, 16e, 19b and 19e were the most NO releasers (3.06, 2.15, 3.17 and 2.54% respectively). Docking studies were carried out to explain the interaction of 16a-f and 19a-f with the target enzymes. Docking mode of final designed compounds with celecoxib (ID: 3LN1) represented that their triazole ring adopted as the core aryl in Y shaped structure. Regarding EGFR inhibition, docking was carried out with ID: 1M17. The internal oxime serious was more active as anticancer because of their ability to form extra HBs with receptor cleft.