138907-71-8

Basic information

• Product Name: 5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: SALOR-INT L251496-1EA;ETHYL 5-AMINO-1-(4-BROMOPHENYL)-1H-PYRAZOLE-4-CARBOXYLATE;BUTTPARK 87\09-21;5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• CAS NO: 138907-71-8
• Molecular Formula: C12H12BrN3O2
• Molecular Weight: 310.15
• Mol File: 138907-71-8.mol

Chemical Properties

• Boiling Point: 423.6 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: /
• Density: 1.57 g/cm³
• Vapor Pressure: 2.2E-07mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(138907-71-8)
• EPA Substance Registry System: 5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(138907-71-8)

Safety Data

• Hazardous Substances Data: 138907-71-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is used as a building block in organic synthesis for the creation of more complex molecules. Its unique structure allows for the development of a wide range of chemical compounds.
Used in Chemical Research:
In the field of chemical research, 5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER serves as an intermediate, facilitating the exploration of new chemical reactions and the synthesis of novel compounds.
Used in Pharmaceutical Development:
5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is used as a precursor in the development of pharmaceuticals. Its specific properties may contribute to the creation of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, 5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is utilized as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides, due to its reactive functional groups.
Used in the Production of Fine Chemicals:
5-AMINO-1-(4-BROMO-PHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is employed in the synthesis of fine chemicals, which are high-purity, specialty chemicals used in various industries, including cosmetics, fragrances, and flavorings.

InChI:InChI=1/C12H12BrN3O2/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 
• 589-21-9 (4-bromophenyl)hydrazine 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 94-05-3 2-cyano-3-ethoxyacrylic acid ethyl ester 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 
• 144918-37-6 (E)-ethyl 2-cyano-3-ethoxyacrylate 

Downstream Products

• 1235034-86-2 1-(4-bromophenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 1235034-87-3 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 1235034-88-4 4-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol 
• 72194-27-5 1-(4-bromophenyl)-1H-pyrazol-5-amine 

Relevant articles and documents

The optimization and characterization of functionalized sulfonamides derived from sulfaphenazole against Mycobacterium tuberculosis with reduced CYP 2C9 inhibition

In this study, a series of sulfonamide compounds was designed and synthesized through the systematic optimization of the antibacterial agent sulfaphenazole for the treatment of Mycobacterium tuberculosis (M. tuberculosis). Preliminary results indicate that the 4-aminobenzenesulfonamide moiety plays a key role in maintaining antimycobacterial activity. Compounds 10c, 10d, 10f and 10i through the optimization on phenyl ring at the R2 site on the pyrazole displayed promising antimycobacterial activity paired with low cytotoxicity. In particular, compound 10d displayed good activity (MIC = 5.69 μg/mL) with low inhibition of CYP 2C9 (IC50 > 10 μM), consequently low potential risk of drug-drug interaction. These promising results provide new insight into the combination regimen using sulfonamide as one component for the treatment of M. tuberculosis.

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.

Discovery of a potent and selective BCL-XLinhibitor with in vivo activity

A-1155463, a highly potent and selective BCL-XLinhibitor, was discovered through nuclear magnetic resonance (NMR) fragment screening and structure-based design. This compound is substantially more potent against BCL-XL-dependent cell lines relative to our recently reported inhibitor, WEHI-539, while possessing none of its inherent pharmaceutical liabilities. A-1155463 caused a mechanism-based and reversible thrombocytopenia in mice and inhibited H146 small cell lung cancer xenograft tumor growth in vivo following multiple doses. A-1155463 thus represents an excellent tool molecule for studying BCL-XLbiology as well as a productive lead structure for further optimization.

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.

HETEROCYCLIC COMPOUNDS AND METHODS OF USE

In one aspect, the present invention provides for a compound of Formula I; in which the variable X1a, X1b, X1c, X1d, Q, A, R1, B, L, E, and the subscripts m and n have the meanings as described herein. In another aspect, the present invention provides for pharmaceutical compositions comprising compounds of Formula I as well as methods for using compounds of Formula I for the treatment of diseases and conditions (e.g., cancer, thrombocythemia, etc) characterized by the expression or over-expression of Bcl-2 anti-apoptotic proteins, e.g., of anti-apoptotic Bcl-xL proteins.

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.

Antibacterial compounds

The present invention provides compounds having useful antibacterial activity and pharmaceutical compositions comprising one or more of these compounds. The invention further relates to a method of treating a bacterial infection in a patient, comprising a