Oxolinic acid

Base Information

• Chemical Name: Oxolinic acid
• CAS No.: 14698-29-4
• Molecular Formula: C13H11NO5
• Molecular Weight: 261.234
• Hs Code.: 29349990
• European Community (EC) Number: 238-750-8
• NSC Number: 758177,110364
• UNII: L0A22B22FT
• DSSTox Substance ID: DTXSID1021089
• Nikkaji Number: J8.514F
• Wikipedia: Oxolinic_acid
• Wikidata: Q287840
• NCI Thesaurus Code: C76921
• RXCUI: 7798
• Metabolomics Workbench ID: 52726
• ChEMBL ID: CHEMBL416755
• Mol file: 14698-29-4.mol

Synonyms:Acid, Oxolinic;Gramurin;Oxolinate, Sodium;Oxolinic Acid;Sodium Oxolinate

Chemical Property of Oxolinic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 9.24E-10mmHg at 25°C
• Melting Point: 314-316 °C (dec.)
• Refractive Index: 1.638
• Boiling Point: 473.2 °C at 760 mmHg
• PKA: 5.94±0.20(Predicted)
• Flash Point: 240 °C
• PSA: 77.76000
• Density: 1.483 g/cm³
• LogP: 1.44830
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in 0.5N NaOH with warming
• Water Solubility.: 3.214mg/L(temperature not stated)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 261.06372245
• Heavy Atom Count: 19
• Complexity: 446

Purity/Quality:

99.0%Min ^*data from raw suppliers

Oxolinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25-60-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O
• Description: Developed in Japan in the 1970s, oxolinic acid belongs to the family of quinolone antibiotic, which is a synthetic antimicrobial agent aiming at gram-negative bacteria, especially those responsible for urinary tract infections. It is also commonly used in clinical for microbiological antimicrobial susceptibility tests against gram negative microbial isolates, providing antibiotic treatment options for infected patients. It can serve as a selective agent in several types of isolation media, for example, to isolate Gardnerella vaginalis. Besides, oxolinic acid can be applied in agriculture, which has proved to be effective against the seed-borne pathogen, such as Burkholderia glumae, a bacteria inducing grain rot, sheath rot, seedling rot, and bacterial panicle blight. Oxolinic acid works by targeting DNA gyrase or topoisomerase II, enzymes vital for DNA synthesis, which ultimately inhibits DNA synthesis and cell division. Bacterial DNA gyrase is a heterodimeric type II topoisomerase that negatively supercoils circular double-stranded DNA. Oxolinic acid is a quinolone antibiotic that inhibits bacterial DNA gyrase, but not eukaryotic topoisomerases, reversibly binding gyrase subunit A in gyrase-DNA complexes, blocking supercoiling activity and inhibiting DNA synthesis at 0.5-5 μg/ml. Oxolinic acid also blocks neuronal uptake of dopamine in mammals (IC50 = 4.3 μM), leading to an increase in locomotor activity.
• Uses: Oxolinic acid is used to study new transmissible resistance mechanisms qnrA, qnrB, qnrS, and aac(6′)Ib-cr, in Escherichia coli and Salmonella enterica. Oxolinic acid is added to culture medium for the isolation of Gardnerella vaginalis. Oxolinic acid is a quinolone antibiotic used for studies on DNA winding and coiling and for studies on dopaminergic neurotransmission processes. It is used to study new transmissible resistance mechanisms qnrA, qnrB, qnrS, and aac(6′)Ib-cr, in Escherichia Quinolone antibacterial.
• Therapeutic Function: Antibacterial (urinary)

Technology Process of Oxolinic acid

There total 19 articles about Oxolinic 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: 93.0%

ethyl 5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo<4,5-g>quinoline-7-carboxylate (16172-03-5) → oxolinic Acid (14698-29-4)

Guidance literature:

With water; sodium hydroxide; for 0.05h; Microwave irradiation;

DOI:10.1002/jhet.430

Reference yield: 92.4%

Ethyl α-ethoxycarbonyl-β-N-(5-benzodioxolyl)-N-ethylaminoacrylate (32953-23-4) → oxolinic Acid (14698-29-4)

Guidance literature:

Ethyl α-ethoxycarbonyl-β-N-(5-benzodioxolyl)-N-ethylaminoacrylate; With sulfuric acid; acetic anhydride; at 80 - 130 ℃; for 4h;

In water; at 90 ℃; for 3h;

Reference yield: 90.0%

→ oxolinic Acid (14698-29-4)

Guidance literature:

upstream raw materials:

3-acetyl-1-ethyl-6,7-methylenedioxy-4-oxo-1,4-dihydroquinoline

Ethyl α-ethoxycarbonyl-β-N-(5-benzodioxolyl)-N-ethylaminoacrylate

8-amino-7-carboxy-5-ethyl-[1,3]dioxolo[4,5-g]quinolinium betaine

8-amino-7-ethoxycarbonyl-5-ethyl-[1,3]dioxolo[4,5-g]quinolinium; iodide

Downstream raw materials:

nitrile of 1-ethyl-6,7-methylenedioxy-4-oxo-1,4-dihydroquinoline-3-carbonic acid

Benzyl 3-N-(1-Ethyl-1,4-Dihydro-6,7-Methylenedioxy-4-Oxoquinoline-3-Carbonyl)Aminopropionate

Ethyl 4-N-(1-Ethyl-1,4-Dihydro-6,7-Methylenedioxy-4-Oxoquinoline-3-Carbonyl)Aminomethylcyclohexanecarboxylate

(S)-2-(5-ethyl-8-oxo-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxamido)-3-methylbutanoate

Refernces

Synthesis of "Dithio-oxolinic Acid"

10.1007/BF00810878

The research focuses on the synthesis of "Dithio-oxolinic Acid," a sulfur analog of Oxolinic Acid, which is part of a new class of synthetic chemotherapeutic agents known as Quinolones. The purpose of the study was to develop a method for synthesizing this compound, which could potentially exhibit antibacterial activity. The process involved the reduction of 5-amino-benzo-1,3-dithiol-2-thion using Diisobutylaluminiumhydrid (DIBAL) or Boran Methylsulfid (BMS) to obtain 5-amino-benzo-1,3-dithiol, which was then condensed with Ethoxymethylenmalons?urediethylester (EMME) to form an intermediate. This intermediate underwent a Gould-Jacobs reaction and subsequent alkylation to yield a mixture of isomers, which were separated by crystallization or chromatography. The final product, Dithio-oxolinic Acid (6a), showed antibacterial activity at higher concentrations and was found to be more active than a related compound (6b). Key chemicals used in the synthesis process included 5-Nitro-benzodithiol-2-thion, DIBAL, BMS, EMME, Dowtherm, Triethylphosphat, and K2CO3, among others.