6076-13-7

Usage

Uses

Used in Pharmaceutical Industry:
INDAZOLE-3-CARBOXYLIC ACID is used as a key intermediate for the synthesis of various pharmaceuticals due to its ability to be readily incorporated into complex molecular structures, enhancing the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
INDAZOLE-3-CARBOXYLIC ACID is utilized as a starting material for the creation of agrochemicals, contributing to the advancement of crop protection agents and other agricultural products that require its unique chemical properties.
Used in Drug Development:
INDAZOLE-3-CARBOXYLIC ACID is employed as a precursor in the development of indazole-based drugs, leveraging its potential biological activities such as antitumor and anti-inflammatory effects for the treatment of various diseases.
Used in Organic Chemistry Research:
INDAZOLE-3-CARBOXYLIC ACID serves as a model compound in organic chemistry research, facilitating the exploration of new synthetic pathways and the discovery of novel chemical reactions that can be applied across different fields of chemistry.

InChI:InChI=1/C23H23N3O2/c27-23(28)20-10-8-18(9-11-20)16-24-26-14-12-25(13-15-26)17-21-6-3-5-19-4-1-2-7-22(19)21/h1-11,16H,12-15,17H2,(H,27,28)/b24-16+

Upstream product

• 771-12-0 α,2-Dioxocyclohexaneacetic Acid 
• 606-26-8 o-nitrobenzohydrazide 
• 4426-72-6 hydrazine carboxamide 
• 108-94-1 cyclohexanone 
• 890005-22-8 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole 
• 6425-41-8 N-cyclohexylmorpholine 
• 387-89-3 2-(2,2,2-trifluoroacetyl)cyclohexanone 
• 5396-14-5 ethyl 2-oxo-2-(2-oxocyclohexyl)acetate 
• 4492-02-8 ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate 
• 86990-99-0 (4,5,6,7-tetrahydro-1⁽²⁾H-indazol-3-yl)-acetonitrile 

Relevant academic research and scientific papers

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.

Pyrazole derivatives as partial agonists for the nicotinic acid receptor

Nicotinic acid as a hypolipidemic agent appears unique due to its potential to increase HDL cholesterol levels to a greater extent than other drugs. However, it has some side effects, among which severe skin flushing is the most frequent and often limits patients' compliance. In a search for novel agonists for the recently identified and cloned G protein-coupled nicotinic acid receptor, we synthesized a series of substituted pyrazole-3-carboxylic acids that proved to have substantial affinity for this receptor. The affinities were measured by inhibition of [3H] nicotinic acid binding to rat spleen membranes. Potencies and intrinsic activities relative to nicotinic acid were determined by their effects on [35S]GTPγS binding to rat adipocyte and spleen membranes. Interestingly, most compounds were partial agonists. In particular, 2-diazabicyclo-[3,3,O 4,8]octa-3,8-diene-3-carboxylic acid (4c) and 5-propylpyrazole-3-carboxylic acid (4f) proved active with Ki values of approximately 0.15 μM and EC50 values of approximately 6 μM, while their intrinsic activity was only ～50% when compared to nicotinic acid. Even slightly more active was 5-butylpyrazole-3-carboxylic acid (4g) with a Ki value of 0.072 μM, an EC50 value of 4.12 μM, and a relative intrinsic activity of 75%. Of the aralkyl derivatives, 4q (5-(3-chlorobenzyl)pyrazole-3-carboxylic acid) was the most active with a relatively low intrinsic activity of 39%. Partial agonism of the pyrazole derivatives was confirmed by inhibition of G protein activation in response to nicotinic acid by these compounds. The pyrazoles both inhibited the maximum effect elicited by 100 μM nicotinic acid and concentration dependently shifted nicotinic acid concentration-response curves to the right, pointing to a competive mechanism of action.

CLEAVAGE REACTIONS USING BASIC HYDROGEN PEROXIDE. A METHOD FOR DEBLOCKING p-NITROBENZYL PROTECTED BASES AND PHENOLS

The hydrolysis of certain nitriles with basic hydrogen peroxide is accompanied by an oxidative cleavage reaction giving the lower homologue carboxylic acid.Under the same conditions, p-nitrobenzylated bases and phenols yield the corresponding N-H base or phenol respectively.