15563-03-8

Basic information

• Product Name: N-butyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide
• CAS NO: 15563-03-8
• Molecular Formula: C₁₁H₁₆N₄O₂
• Molecular Weight: 236.2703
• Mol File: 15563-03-8.mol
• Article Data: 1

Chemical Properties

• Density: 1.159g/cm³
• Refractive Index: 1.537
• CAS DataBase Reference: N-butyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-butyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide(15563-03-8)
• EPA Substance Registry System: N-butyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide(15563-03-8)

Safety Data

• Hazardous Substances Data: 15563-03-8(Hazardous Substances Data)

Upstream product

• 2845-82-1 5-(pyridin-4-yl)-3H-1,3,4-oxadiazol-2-one 
• 109-73-9 N-butylamine 
• 54-85-3 isoniazid 
• 111-36-4 n-butyl isocyanide 
• 56863-96-8 isonicotinoyl-urea 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 

Relevant articles and documents

New lipophilic isoniazid derivatives and their 1,3,4-oxadiazole analogues: Synthesis, antimycobacterial activity and investigation of their mechanism of action

The development of novel drugs is essential for the treatment of tuberculosis and other mycobacterial infections in future. A series of N-alkyl-2-isonicotinoylhydrazine-1-carboxamides was synthesized from isoniazid (INH) and then cyclized to N-alkyl-5-(pyridin-4-yl)-1,3,4-oxadiazole-2-amines. All derivatives were characterised spectroscopically. The compounds were screened for their in vitro antimycobacterial activity against susceptible and multidrug-resistant Mycobacterium tuberculosis (Mtb.) and nontuberculous mycobacteria (NTM; M. avium, M. kansasii). The most active carboxamides were substituted by a short n-alkyl, their activity was comparable to INH with minimum inhibitory concentrations (MICs) against Mtb. of 0.5–2 μM. Moreover, they are non-toxic for HepG2, and some of them are highly active against INH-resistant NTM (MICs ≥4 μM). Their cyclization to 1,3,4-oxadiazoles did not increase the activity. The experimentally proved mechanism of action of 2-isonicotinoylhydrazine-1-carboxamides consists of the inhibition of enoyl-ACP reductase (InhA) in a way similar to INH, which is blocking the biosynthesis of mycolic acids. N-Dodecyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine as the most efficacious oxadiazole inhibits growth of both susceptible and drug-resistant Mtb. strains with uniform MIC values of 4–8 μM with no cross-resistance to antitubercular drugs including INH. The mechanism of action is not elucidated but it is different from INH. Obtained results qualify these promising derivatives for further investigation.