3376-95-2

Basic information

• Product Name: 2-ethylisonicotinamide
• Synonyms: 2-ethylisonicotinamide;4-Pyridinecarboxamide,2-ethyl-(9CI);2-Ethyl-4-pyridinecarboxamide;2-Ethylpyridine-4-carboxamide;2-Ethylpyridin-4-carboxaMide;2-Ethyl-4-PyridinecarboxaMide (2-EthylisonicotinaMide)
• CAS NO: 3376-95-2
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.1778
• EINECS: 222-170-7
• Product Categories: AMIDE
• Mol File: 3376-95-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 131 °C
• Boiling Point: 279.2°Cat760mmHg
• Flash Point: 122.7°C
• Appearance: /
• Density: 1.119g/cm³
• Vapor Pressure: 0.00407mmHg at 25°C
• Refractive Index: 1.551
• PKA: 15.07±0.50(Predicted)
• CAS DataBase Reference: 2-ethylisonicotinamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ethylisonicotinamide(3376-95-2)
• EPA Substance Registry System: 2-ethylisonicotinamide(3376-95-2)

Safety Data

• Hazardous Substances Data: 3376-95-2(Hazardous Substances Data)

Usage

Description

2-Ethylisonicotinamide is a chemical compound that serves as a metabolite of Ethionamide (E890420), a medication with tuberculostatic activity. It plays a significant role in the treatment of tuberculosis by contributing to the bactericidal effects of the parent drug.

Uses

Used in Pharmaceutical Industry:
2-Ethylisonicotinamide is used as an active metabolite for its tuberculostatic activity. It is particularly effective in the treatment of tuberculosis, as it helps to inhibit the growth and proliferation of Mycobacterium tuberculosis, the bacterium responsible for the disease. Its role in the pharmaceutical industry is crucial, as it aids in the development of more effective anti-tuberculosis drugs and contributes to the overall management of the disease.

InChI:InChI=1/C8H10N2O/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)

Upstream product

• 1531-16-4 methyl 2-ethylpyridine-4-carboxylate 
• 4104-77-2 2-ethyl-6-chloro-isonicotinic acid methyl ester 
• 1531-18-6 2-ethyl-4-pyridinecarbonitrile 
• 29840-73-1 2-bromopyridine-4-carboxamide 
• 6107-37-5 ethylzinc bromide 
• 67-56-1 methanol 
• 536-33-4 ethionamide 
• 865-05-4 nicotinamide adenine dinucleotide 
• 100-71-0 2-Ethylpyridine 
• 77287-34-4 formamide 
• 4009-26-1 2-ethyl-6-chloro-isonicotinic acid ethyl ester 
• 15862-61-0 ethyl 2-ethylisonicotinate 

Downstream Products

• 536-33-4 ethionamide 
• 1531-18-6 2-ethyl-4-pyridinecarbonitrile 

Relevant articles and documents

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Efficient analoging around ethionamide to explore thioamides bioactivation pathways triggered by boosters in Mycobacterium tuberculosis

Ethionamide is a key antibiotic prodrug of the second-line chemotherapy regimen to treat tuberculosis. It targets the biosynthesis of mycolic acids thanks to a mycobacterial bioactivation carried out by the Baeyer-Villiger monooxygenase EthA, under the control of a transcriptional repressor called EthR. Recently, the drug-like molecule SMARt-420, which triggers a new transcriptional regulator called EthR2, allowed the derepression a cryptic alternative bioactivation pathway of ethionamide. In order to study the bioactivation of a collection of thioisonicotinamides through the two bioactivation pathways, we developed a new two-step chemical pathway that led to the efficient synthesis of eighteen ethionamide analogues. Measurements of the antimycobacterial activity of these derivatives, used alone and in combination with boosters BDM41906 or SMARt-420, suggest that the two different bioactivation pathways proceed via the same mechanism, which implies the formation of similar metabolites. In addition, an electrochemical study of the aliphatic thioisonicotinamide analogues was undertaken to see whether their oxidation potential correlates with their antitubercular activity measured in the presence or in the absence of the two boosters.

A pyridine amide synthetic method of compound

The invention discloses a method for synthesizing a pyridine-amide compound. The method comprises the steps of carrying out hydrolysis on a pyridine cyanogen compound shown by a formula II as a starting material in water as a solvent in the presence of an ETS-10 molecular sieve as a catalyst, heating to 100-150 DEG C, reacting until the reaction, which is tracked and detected by virtue of TLC (Thin-Layer Chromatography), is completed and carrying out post-treatment on the reaction solution to obtain the pyridine-amide compound represented by the formula I. According to the method disclosed by the invention, the ETS-10 molecular sieve is taken as a catalyst to carry out hydrolysis on pyridine cyanogen to obtain a single pyridine-amide product, the conversion rate is 100%, the yield is above 95% and the catalyst can be repeatedly used for at least 5 times.