Isonicotinoylhydrazonopyruvic acid

Base Information

• Chemical Name: Isonicotinoylhydrazonopyruvic acid
• CAS No.: 1081-50-1
• Molecular Formula: C9H9 N3 O3
• Molecular Weight: 207.189
• NSC Number: 97221
• UNII: VY56R86DL7
• DSSTox Substance ID: DTXSID1057618
• Nikkaji Number: J27.998F
• Wikidata: Q27149666
• ChEMBL ID: CHEMBL3187728
• Mol file: 1081-50-1.mol

Synonyms:Isoniazid pyruvate;Isoniazid pyruvate, (Z)-;VY56R86DL7;UNII-VY56R86DL7;DTXSID1057618;4-Pyridinecarboxylic acid, (2Z)-2-(1-carboxyethylidene)hydrazide;1393599-25-1;4-Pyridinecarboxylic acid, (1-carboxyethylidene)hydrazide;Isonicotinoylhydrazonopyruvic acid;NSC 97221;1081-50-1;BRN 0185611;L 1011;C9H9N3O3;ISONICOTINIC ACID, (1-CARBOXYETHYLIDENE)HYDRAZIDE;CHEMBL3187728;DTXCID2031407;NSC97221;Tox21_113689;NSC-97221;NCGC00249913-01;LS-84861;CAS-1081-50-1;Q27149666

Chemical Property of Isonicotinoylhydrazonopyruvic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.34g/cm³
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 207.06439116
• Heavy Atom Count: 15
• Complexity: 282

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=NNC(=O)C1=CC=NC=C1)C(=O)O
• Isomeric SMILES: C/C(=N/NC(=O)C1=CC=NC=C1)/C(=O)O
• General Description: (2Z)-2-[(Pyridin-4-ylcarbonyl)hydrazono]propanoic acid, also known as pyruvic acid isonicotinoylhydrazone, is a derivative of the antitubercular drug isoniazid, designed to enhance lipophilicity and antimycobacterial activity. It serves as a key scaffold in the synthesis of potent InhA inhibitors, demonstrating high efficacy against drug-sensitive and multidrug-resistant *Mycobacterium tuberculosis* (MIC values as low as ≤0.03 μM) as well as nontuberculous mycobacteria. (2Z)-2-[(pyridin-4-ylcarbonyl)hydrazono]propanoic acid's mechanism involves inhibition of enoyl-acyl carrier protein reductase (InhA), disrupting mycolic acid biosynthesis, and it exhibits a favorable pharmaco-toxicological profile with no cytotoxicity in HepG2 cells. Its structural modifications, such as esterification or incorporation into diorganotin(IV) complexes, further expand its potential as a promising antitubercular agent with improved properties over isoniazid.

Technology Process of Isonicotinoylhydrazonopyruvic acid

There total 3 articles about Isonicotinoylhydrazonopyruvic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

isoniazid (54-85-3,7640-37-1) + 2-oxo-propionic acid (127-17-3) → (E)-2-(2-isonicotinoylhydrazineylidene)propanoic acid (1081-50-1)

Guidance literature:

In methanol; for 2h; Reflux;

DOI:10.1016/j.ejmech.2021.113668

Reference yield: 95.0%

isoniazid (54-85-3,7640-37-1) + 2-oxo-propionic acid (127-17-3) → 2-isonicotinoylhydrazono-propionic acid (1081-50-1)

Guidance literature:

In ethanol;

DOI:10.1016/j.jorganchem.2004.12.037 DOI:10.1002/ejic.200500412

Reference yield:

→ 2-isonicotinoylhydrazono-propionic acid (1081-50-1)

Guidance literature:

Brenztraubensaeure, Isonicotinoylhydrazid;

DOI:10.1007/BF00778278

upstream raw materials:

isoniazid

2-oxo-propionic acid