5323-57-9

Basic information

• Product Name: QUINOLINE-2,4-DICARBOXYLIC ACID
• Synonyms: QUINOLINE-2,4-DICARBOXYLIC ACID;AKOS BC-0591;2,4-QUINOLINEDICARBOXYLIC ACID;QUINOLINE-2,4-DICARBOXYLIC ACID FOR SYNT
• CAS NO: 5323-57-9
• Molecular Formula: C₁₁H₇NO₄
• Molecular Weight: 217.18
• Product Categories: Quinolines, Quinazolines and derivatives
• Mol File: 5323-57-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 236 °C (decomp)
• Boiling Point: 451.4°Cat760mmHg
• Flash Point: 226.8°C
• Appearance: /
• Density: 1.531g/cm³
• Vapor Pressure: 6.17E-09mmHg at 25°C
• Refractive Index: 1.72
• PKA: 2.14±0.10(Predicted)
• CAS DataBase Reference: QUINOLINE-2,4-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: QUINOLINE-2,4-DICARBOXYLIC ACID(5323-57-9)
• EPA Substance Registry System: QUINOLINE-2,4-DICARBOXYLIC ACID(5323-57-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 5323-57-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H7NO4/c13-10(14)7-5-9(11(15)16)12-8-4-2-1-3-6(7)8/h1-5H,(H,13,14)(H,15,16)

Upstream product

• 38256-25-6 dimethyl (E)-2-oxoglutaconate 
• 91-56-5 indole-2,3-dione 
• 204847-08-5 2-(5-methylfuran-2-yl)quinoline-4-carboxylic acid 

Downstream Products

• 486-74-8 4-quinolinic acid 
• 91-22-5 quinoline 
• 91799-73-4 quinoline-4-carboxylic acid chloride hydrochloride 
• 10447-29-7 ethyl quinoline-4-carboxylate 
• 146136-78-9 2,4-diamino-quinoline 
• 157915-68-9 2-amino-quinoline-4-carboxylic acid 
• 32743-31-0 quinoline-2,4-dicarboxylic acid diamide 

Relevant articles and documents

Oxidative Reactivities of 2-Furylquinolines: Ubiquitous Scaffolds in Common High-Throughput Screening Libraries

High-throughput screening (HTS) was employed to discover APOBEC3G inhibitors, and multiple 2-furylquinolines (e.g., 1) were found. Dose-response assays with 1 from the HTS sample, as well as commercial material, yielded similar confirmatory results. Interestingly, freshly synthesized and DMSO-solubilized 1 was inactive. Repeated screening of the DMSO aliquot of synthesized 1 revealed increasing APOBEC3G inhibitory activity with age, suggesting that 1 decomposes into an active inhibitor. Laboratory aging of 1 followed by analysis revealed that 1 undergoes oxidative decomposition in air, resulting from a [4 + 2] cycloaddition between the furan of 1 and 1O2. The resulting endoperoxide then undergoes additional transformations, highlighted by Baeyer-Villager rearrangements, to deliver lactam, carboxylic acid, and aldehyde products. The endoperoxide also undergoes hydrolytic opening followed by further transformations to a bis-enone. Eight structurally related analogues from HTS libraries were similarly reactive. This study constitutes a cautionary tale to validate 2-furylquinolines for structure and stability prior to chemical optimization campaigns.

Quinoline-2,4-dicarboxylic acids: Synthesis and evaluation as inhibitors of the glutamate vesicular transport system

Twenty-six quinoline-2,4-dicarboxylic acids (QDC's) were synthesized by a modified Doebner-von Miller pathway and tested as inhibitors against the glutamate vesicular transport (GVT) protein. The QDC's were active as inhibitors with the most potent QDC's found to contain halogens at the 6-/8-position, a hydroxyl at the 8-position, or a tethered aromatic moiety at the 6- or 7-position of the quinoline.