23688-89-3

Usage

Uses

Used in Pharmaceutical Research and Development:
6-Chloropyrazine-2-carboxylic acid is utilized as a building block in organic synthesis and pharmaceutical research for its ability to contribute to the development of new pharmaceutical drugs. Its unique structure allows it to be a key component in the creation of molecules with specific therapeutic targets.
Used in Agrochemical Production:
6-Chloropyrazine-2-carboxylic acid also finds use in the production of agrochemicals, where its biological properties can be harnessed to create effective products for agricultural applications, potentially enhancing crop protection and yield.
Used in Medicinal Chemistry for Antimicrobial Agents:
6-Chloropyrazine-2-carboxylic acid is employed as an antimicrobial agent due to its studied activities against various microorganisms, making it a valuable asset in the discovery and development of new antibiotics and antiseptic compounds.
Used in Medicinal Chemistry for Antifungal Agents:
Similarly, its antifungal activities position 6-Chloropyrazine-2-carboxylic acid as a potential candidate for the development of antifungal medications, addressing the need for novel treatments in the realm of fungal infections.

InChI:InChI=1/C5H3ClN2O2/c6-4-2-7-1-3(8-4)5(9)10/h1-2H,(H,9,10)

Upstream product

• 23611-75-8 6-chloro-pyrazine-2-carboxylic acid methyl ester 
• 148673-71-6 6-chloropyrazine-2-carboxylic acid chloride 
• 874-54-4 pyrazine-2-carboxylic acid-4-oxide 
• 98-97-5 2-pyrazylcarboxylic acid 
• 10025-87-3 trichlorophosphate 
• 770-00-3 methylester of pyrazinecarboxylic acid 4-oxide 
• 6164-79-0 methyl pyrazine-2-carboxylate 

Downstream Products

• 111374-47-1 6-chloro-N-(1H-tetrazol-5-yl)-2-pyrazinecarboxamide 
• 148673-71-6 6-chloropyrazine-2-carboxylic acid chloride 
• 652153-48-5 (6-chloropyrazin-2-yl)carbamic acid tert-butyl ester 
• 111374-19-7 6-(dimethylamino)-N-(1H-5-tetrazolyl)pyrazine-2-carboxamide 
• 111374-21-1 6-(1-pyrrolidinyl)-N-(1H-tetrazol-5-yl)-2-pyrazine-5-carboxamide 
• 36070-79-8 6-chloro-pyarzine-2-carboxamide 
• 1223444-91-4 6-chloropyrazine-2-carboxylic acid methoxymethylamide 
• 1194687-77-8 6-chloro-N-(3-isopropoxyphenyl)pyrazine-2-carboxamide 
• 1194687-63-2 (3aR,6aS)-tert-butyl 5-(6-(m-tolylcarbamoyl)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate 
• 1194687-69-8 (3aS,6aS)-tert-butyl 5-(6-(m-tolylcarbamoyl)pyrazin-2-yl)hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate 
• 1194687-78-9 (3aR,6aS)-tert-butyl 5-(6-(3-isopropoxyphenylcarbamoyl)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate 
• 33332-49-9 6-Aminopyrazinecarboxamide 
• 1537902-08-1 6-(2-phenylethylamino)pyrazine-2-carboxamide 
• 1537902-09-2 6-(3-phenylpropylamino)pyrazine-2-carboxamide 

Relevant academic research and scientific papers

Synthesis and in vitro evaluation of diverse heterocyclic diphenolic compounds as inhibitors of DYRK1A

Dual-specificity tyrosine phosphorylation-related kinase 1A (DYRK1A) is a dual-specificity protein kinase that catalyses phosphorylation and autophosphorylation. Higher DYRK1A expression correlates with cancer, in particular glioblastoma present within the brain. We report here the synthesis and biological evaluation of new heterocyclic diphenolic derivatives designed as novel DYRK1A inhibitors. The generation of these heterocycles such as benzimidazole, imidazole, naphthyridine, pyrazole-pyridines, bipyridine, and triazolopyrazines was made based on the structural modification of the lead DANDY and tested for their ability to inhibit DYRK1A. None of these derivatives showed significant DYRK1A inhibition but provide valuable knowledge around the importance of the 7-azaindole moiety. These data will be of use for developing further structure-activity relationship studies to improve the selective inhibition of DYRK1A.

Alkylamino derivatives of pyrazinamide: Synthesis and antimycobacterial evaluation

A series of pyrazinamide derivatives with alkylamino substitution was designed, synthesized and tested for their ability to inhibit the growth of selected mycobacterial, bacterial and fungal strains. The target structures were prepared from the corresponding 5-chloro (1) or 6-chloropyrazine-2-carboxamide (2) by nucleophilic substitution of chlorine by various non-aromatic amines (alkylamines). To determine the influence of alkyl substitution, corresponding amino derivatives (1a, 2a) and compounds with phenylalkylamino substitution were prepared. Some of the compounds exerted antimycobacterial activity against Mycobacterium tuberculosis H37Rv significantly better than standard pyrazinamide and corresponding starting compounds (1 and 2). Basic structure-activity relationships are presented. Only weak antibacterial and no antifungal activity was detected.

Substituted N-benzylpyrazine-2-carboxamides: Synthesis and biological evaluation

A series of twelve amides was synthesized via aminolysis of substituted pyrazinecarboxylic acid chlorides with substituted benzylamines. Compounds were characterized with analytical data and assayed in vitro for their antimycobacterial, antifungal, antibacterial and photosynthesis-inhibiting activity. 5-tert-Butyl-6-chloro-N-(4-methoxybenzyl)pyrazine-2-carboxamide (12) has shown the highest antimycobacterial activity against Mycobacterium tuberculosis (MIC = 6.25 μg/mL), as well as against other mycobacterial strains. The highest antifungal activity against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 5-chloro-N-(3- trifluoromethylbenzyl)- pyrazine-2-carboxamide (2, MIC = 15.62 μmol/L). None of the studied compounds exhibited any activity against the tested bacterial strains. Except for 5-tert-butyl-6-chloro-N-benzylpyrazine-2-carboxamide (9, IC50 = 7.4 μmol/L) and 5-tert-butyl-6-chloro-N-(4-chlorobenzyl) pyrazine-2-carboxamide (11, IC50 = 13.4 μmol/L), only moderate or weak photosynthesis-inhibiting activity in spinach chloroplasts (Spinacia oleracea L.) was detected.

Structure-activity studies of diazabicyclo[3.3.0]octane-substituted pyrazines and pyridines as Potent α4β2 nicotinic acetylcholine receptor ligands

A series of diazabicyclo[3.3.0]octane substituted pyridines and pyrazines was synthesized and characterized at the α4β2 neuronal nicotinic acetylcholine receptor (nAChR). The compounds were designed to mimic the profile of ABT-089, high affinity binding ligand for the α4β2 nAChR, with limited agonist activity. Carboxamide derivatives of 3-(diazabicyclo[3.3.0] octane)-substituted pyridines or 2-(diazabicyclo[3.3.0]octane)-substituted pyrazines were found to have the desired binding and activity profile. The structure-activity relationship of these compounds is presented.

Selective Ligands for the Neuronal Nicotinic Receptors and Uses Thereof

The present application describes selective ligands of formula (I) for neuronal nicotinic receptors (NNRs), more specifically for the α4β2 NNR subtype, compositions thereof, and methods of using the same, wherein X, R1, X, R2, R3, L1, m, n, p, and q are defined in the specification.