21279-64-1

Basic information

• Product Name: 5-chloropyrazine-2-carboxamide
• Synonyms: 5-chloropyrazine-2-carboxamide;5-Chloro-2-pyrazinecarboxamide;EOS-61239
• CAS NO: 21279-64-1
• Molecular Formula: C₅H₄ClN₃O
• Molecular Weight: 157.56
• EINECS: 1312995-182-4
• Mol File: 21279-64-1.mol

Chemical Properties

• Boiling Point: 331.3 °C at 760 mmHg
• Flash Point: 154.2 °C
• Appearance: /
• Density: 1.479 g/cm³
• Vapor Pressure: 0.000157mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5-chloropyrazine-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloropyrazine-2-carboxamide(21279-64-1)
• EPA Substance Registry System: 5-chloropyrazine-2-carboxamide(21279-64-1)

Safety Data

• Hazardous Substances Data: 21279-64-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloropyrazine-2-carboxamide is used as a key intermediate in the synthesis of various pharmaceuticals. Its ability to inhibit the enzyme ribonucleotide reductase, which plays a crucial role in DNA synthesis, makes it a promising candidate for the development of antiviral and anticancer drugs.
Used in Agrochemical Industry:
5-Chloropyrazine-2-carboxamide is utilized as a building block in the synthesis of agrochemicals, such as herbicides and insecticides. Its potential antimicrobial and antifungal properties contribute to the development of effective crop protection agents.
Used in Organic Chemistry:
In the field of organic chemistry, 5-chloropyrazine-2-carboxamide serves as a versatile building block for the creation of more complex molecules. Its unique structure allows for various chemical modifications, enabling the synthesis of novel compounds with diverse applications.

InChI:InChI=1/C5H4ClN3O/c6-4-2-8-3(1-9-4)5(7)10/h1-2H,(H2,7,10)

Upstream product

• 14508-49-7 2-chloropyrazin 
• 77287-34-4 formamide 
• 36070-80-1 5-chloropyrazinoic acid 
• 34604-60-9 5-hydroxypyrazinoic acid 
• 33332-25-1 methyl 5-chloropyrazine-2-carboxylate 
• 768-36-5 2-pyrazinecarboxamide-4-oxide 
• 98-96-4 pyrazinamide 
• 88625-23-4 5-chloropyrazine-2-carbonyl chloride 
• 36070-75-4 5-chloro-2-pyrazinecarbonitrile 

Downstream Products

• 89323-09-1 5-aminopyrazine-2-carboxamide 
• 1537901-91-9 5-(methylamino)pyrazine-2-carboxamide 
• 1537901-92-0 5-(ethylamino)pyrazine-2-carboxamide 
• 1537901-93-1 5-(propylamino)pyrazine-2-carboxamide 
• 1537901-94-2 5-(butylamino)pyrazine-2-carboxamide 
• 1537901-95-3 5-(pentylamino)pyrazine-2-carboxamide 
• 1537901-96-4 5-(hexylamino)pyrazine-2-carboxamide 
• 1537901-97-5 5-(heptylamino)pyrazine-2-carboxamide 
• 1537901-98-6 5-(octylamino)pyrazine-2-carboxamide 
• 1537901-99-7 5-(2-phenylethylamino)pyrazine-2-carboxamide 
• 1537902-00-3 5-(3-phenylpropylamino)pyrazine-2-carboxamide 
• 1352012-47-5 2,2,2-trifluoro-1-(trifluoromethyl)ethyl 4-[2-(5-carbamoylpyrazin-2-ylamino)ethyl]piperidine-1-carboxylate 
• 1352012-75-9 tert-butyl 4-[2-(5-carbamoylpyrazin-2-ylamino)ethyl]piperidine-1-carboxylate 
• 36070-75-4 5-chloro-2-pyrazinecarbonitrile 

Relevant articles and documents

Benzoxaborole Antimalarial Agents. Part 4. Discovery of Potent 6-(2-(Alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles

A series of 6-hetaryloxy benzoxaborole compounds was designed and synthesized for a structure-activity relationship (SAR) investigation to assess the changes in antimalarial activity which result from 6-aryloxy structural variation, substituent modification on the pyrazine ring, and optimization of the side chain ester group. This SAR study discovered highly potent 6-(2-(alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles (9, 27-34) with IC50s = 0.2-22 nM against cultured Plasmodium falciparum W2 and 3D7 strains. Compound 9 also demonstrated excellent in vivo efficacy against P. berghei in infected mice (ED90 = 7.0 mg/kg).

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.

BENZENE OR THIOPHENE DERIVATIVE AND USE THEREOF AS VAP-1 INHIBITOR

The present invention provides a novel benzene derivative or thiophene derivative useful as a VAP-1 inhibitor, or a medicament for the prophylaxis or treatment of a VAP-1 associated disease and the like, namely, a compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a pharmaceutically acceptable salt thereof.

CONDENSED PYRIDINE COMPOUND

The present invention provides a compound having excellent JAK3 inhibitory activity and being useful as an active ingredient of an agent for treating and/or preventing various immune diseases including autoimmune diseases, inflammatory diseases, and allergic diseases. As a result of investigations with respect to novel condensed heterocyclic derivatives, the inventors have verified that a condensed pyridine compound has excellent JAK3 inhibitory activity, thereby completing the present invention. More specifically, it has been verified that since the compound according to the present invention has inhibitory activity against JAK3, the compound is useful as an active ingredient of an agent for treating or preventing diseases caused by undesirable cytokine signal transduction (e.g., rejection during live organ/tissue transplantation, autoimmune diseases, asthma, atopic dermatitis, rheumatism, psoriasis and atherosclerotic disease), or diseases caused by abnormal cytokine signal transduction (e.g., cancer and leukemia).

In vitro antimycobacterial activity of 5-chloropyrazinamide

5-Chloropyrazinamide and 5-chloropyrazinoic acid were evaluated for in vitro activity against Mycobacterium tuberculosis, Mycobacterium bovis, and several nontuberculous mycobacteria by a broth dilution method. 5- Chloropyrazinamide was more active than pyrazinamide against all organisms tested. It is likely that this agent has a different mechanism of action than pyrazinamide.

SYNTHESIS AND 1H AND 13C NMR SPECTRA OF SULFUR DERIVATIVES OF PYRAZINE DERIVED FROM AMIDATION PRODUCT OF 2-CHLOROPYRAZINE AND 6-CHLORO-2-PYRAZINECARBONITRILE. TUBERCULOSTATIC ACTIVITY

Homolytic amidations of 2-chloropyrazine and 6-chloropyrazine-2-carbonitrile have been carried out to obtain products which have been used to prepare sulfur derivatives of pyrazine as potential tuberculostatic agents.The 1H and 13C NMR spectra of the products have been measured and interpreted, and the antituberculotic activity has been evaluated.