84547-87-5

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrazole-3-carboxylic acid, 4-chloro-(9CI) is utilized as a building block for the synthesis of pharmaceutical compounds due to its structural similarity to biologically active molecules. It aids in the development of new drugs with potential therapeutic applications.
Used in Agricultural Industry:
In the agricultural sector, 1H-Pyrazole-3-carboxylic acid, 4-chloro-(9CI) is employed as a precursor in the synthesis of agrochemicals, contributing to the development of new pesticides or other bioactive agents for crop protection and enhancement of agricultural productivity.
Used in Research and Development:
1H-Pyrazole-3-carboxylic acid, 4-chloro-(9CI) serves as a starting material in the synthesis of a variety of organic compounds in research and development. It is instrumental in advancing the understanding of chemical reactions and the creation of novel chemical entities with potential applications in various fields.

InChI:InChI=1/C4H3ClN2O2/c5-2-1-6-7-3(2)4(8)9/h1H,(H,6,7)(H,8,9)

Upstream product

• 15878-08-7 4-chloro-3-methyl-1H-pyrazole 
• 401517-15-5 4-chloro-3-(trifluoromethyl)-1H-pyrazole 
• 98816-35-4 4-chloro-3-methyl-1⁽²⁾H-pyrazole; hydrochloride 
• 1621-91-6 1H-pyrazole-3-carboxylic acid 

Downstream Products

• 717871-75-5 4-chloro-1H-pyrazole-3-carbonyl chloride 

Relevant academic research and scientific papers

3-Substituted pyrazoles and 4-substituted triazoles as inhibitors of human 15-lipoxygenase-1

Investigation of 1N-substituted pyrazole-3-carboxanilides as 15-lipoxygenase-1 (15-LOX-1) inhibitors demonstrated that the 1N-substituent was not essential for activity or selectivity. Additional halogen substituents on the pyrazole ring, however, increased activity. Further development led to triazole-4-carboxanilides and 2-(3-pyrazolyl) benzoxazoles, which are potent and selective 15-LOX-1 inhibitors.

Preparations of 4-substituted 3-carboxypyrazoles

The scopes of three synthetic methods reported for the preparation of an array of 3-pyrazolecarboxylates featuring substituents on position 4 were investigated. The first one is based on the potassium permanganate oxidation of methylpyrazoles. The second starts with the condensation between DMF dimethylacetal and ethyl pyruvate and is followed by the addition of hydrazine hydrochloride. The last one makes use of the cycloaddition of diazomethane on acrylate esters followed by a bromine-based oxidative rearrangement into 4-substituted 3-pyrazole esters.

Pyrazole-3/5-carboxylic acids from 3/5-trifluoromethyl NH-pyrazoles

We report here the transformation of 3/5-trifluoromethylpyrazoles derivative into the corresponding NH-pyrazole-3/5-carboxylic acids. Moreover, from 4- or 5-iodinated-3/5-trifluoromethylpyrazoles building blocks and the use of Suzuki-Miyaura or Negishi reactions followed by the trifluoromethyl hydrolysis, we illustrate short and original accesses to many series of NH-pyrazole-3/5-carboxylic acids otherwise difficult to prepare.

Electrosynthesis of 4-chloropyrazolecarboxylic acids

4-Chlorosubstituted pyrazolecarboxylic acids were synthesized via chlorination of the corresponding acids at the Pt anode in NaCl aqueous solutions under conditions of divided galvanostatic electrolysis. The efficiency of the process depends on the structures of the initial pyrazolecarboxylic acids, particularly, on the donor-acceptor properties of the substituents and on their position in the pyrazole ring. The yields of the 4-chlorosubstituted products of chlorination of pyrazole-3(5)-carboxylic acid, 1-methylpyrazole-5- carboxylic acid, 1-methyl-pyrazole-3-carboxylic acid, 1-ethylpyrazole-3- carboxylic acid, and 1-methyl-3-nitropyrazole- 5-carboxylic acid are 92, 93, 69, 80, and 4%, respectively.

PYRAZOLES USEFUL IN THE TREATMENT OF INFLAMMATION

There is provided compounds of formula (I), wherein R1, R2, X1, X2 and n have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a lipoxygenase (e.g. 15-lipoxygenase) is desired and/or required, and particularly in the treatment of inflammation.

PYRAZOLES USEFUL IN THE TREATMENT OF INFLAMMATION

There is provided compounds of formula (I), wherein R1, R2, X1, X2 and n have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a lipoxygenase (e.g. 15-lipoxygenase) is desired and/or required, and particularly in the treatment of inflammation.

Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof

The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: wherein Ar1, Ar3, A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.