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Usage

Uses

Used in Pharmaceutical Industry:
Xanthurenic acid is used as a caspase activator and a guanylyl cyclase stimulant, playing a role in the regulation of cellular processes and potentially contributing to the development of new therapeutic agents.
Used in Environmental Industry:
Xanthurenic acid is used as a substrate for the synthesis of silica-gel functionalized xanthurenic acid, which serves as an adsorbent for metal ions. This application is crucial for environmental protection and pollution control.
Used in Chemical Synthesis:
Xanthurenic acid is used as a starting material for the synthesis of various compounds, such as N,N′-bis-((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ethers. These compounds are used as fluorescent sensors for detecting magnesium in living cells, which can be beneficial for biological research and medical applications.
Used in Biosensing Applications:
Poly-xanthurenic acid (poly-Xa) is synthesized from xanthurenic acid and is used for biosensing applications. This polymer has potential uses in detecting and monitoring various biological and chemical processes.
Additionally, xanthurenic acid is excreted by pyridoxine-deficient animals after the ingestion of tryptophan, which can be useful in studying the effects of vitamin deficiencies and their impact on animal health.

Purification Methods

It is precipitated by the addition of 2N formic acid to its solution in hot 2M ammonia (charcoal). The solid is filtered off, dried in a vacuum at ~80o in the dark. UV (H2O) has nm ( M-1cm-1): 243 (30,000) and 342 (6,500). The methyl ester has m 262o (from MeOH). It forms Cu2+, Zn2+, Fe2+ and Fe3+ salts. [Beilstein 22 III/IV 2513.]

InChI:InChI=1/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)

Upstream product

• 4008-46-2 methyl 4-hydroxy-8-methoxyquinoline-2-carboxylate 
• 55895-59-5 8-methoxy-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid ethyl ester 
• 607-67-0 4-hydroxy-2-methylquinoline 
• 7101-82-8 dimethyl 2-((2-methoxyphenyl)amino)but-2-enedioate 
• 5934-38-3 4,8-dihydroxy-quinoline-2-carboxylic acid methyl ester 
• 90-04-0 2-methoxy-phenylamine 
• 484-78-6 3-hydroxykynurenine 

Downstream Products

• 14959-84-3 4,8-dihydroxyquinoline 
• 122668-06-8 N-<(4',8'-dihydroxy-2'-quinolyl)carbonyl>-(R)-glutamic acid di-n-pentylamide γ-benzyl ester 
• 1108187-56-9 4-phenylquinolin-8-yl 4-methylbenzenesulfonate 
• 1166262-04-9 4-bromoquinolin-8-yl 4-methylbenzenesulfonate 
• 57334-36-8 4-chloro-8-hydroxyquinoline 
• 1022094-19-4 4-(1H-pyrazol-1-yl)quinolin-8-yl 4-methylbenzenesulfonate 
• 1022094-18-3 (4-chloroquinolin-8-yl)-4-methylbenzenesulfonate 
• 1360172-44-6 C₁₆H₁₂N₂O₃ 
• 406728-28-7 N-[Nα-(4,8-Dihydroxyquinoline-2-carbonyl)-Nδ-trityl-L-glutaminyl]-2,5-dimethoxyaniline 
• 406728-13-0 N-[Nα-(4,8-Dihydroxyquinoline-2-carbonyl)-Nτ-trityl-L-histidinyl]-3,4-dihydroxybenzylamine 
• 406728-07-2 N-[Nα-(4,8-dihydroxyquinoline-2-carbonyl)-Nγ-trityl-L-asparagyl]dopamine 
• 21638-90-4 methyl 8-hydroxyquinoline-2-carboxylate 
• 1571-30-8 8-hydroxy-quinoline-2-carboxylic acid 
• 927833-19-0 4-octyloxy-8-tosyloxyquinoline 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of novel arylcarboxamide derivatives as anti-tubercular agents

Our group has previously reported several indolecarboxamides exhibiting potent antitubercular activity. Herein, we rationally designed several arylcarboxamides based on our previously reported homology model and the recently published crystal structure of the mycobacterial membrane protein large 3 (MmpL3). Many analogues showed considerable anti-TB activity against drug-sensitive (DS) Mycobacterium tuberculosis (M. tb) strain. Naphthamide derivatives 13c and 13d were the most active compounds in our study (MIC: 6.55, 7.11 μM, respectively), showing comparable potency to the first line anti-tuberculosis (anti-TB) drug ethambutol (MIC: 4.89 μM). In addition to the naphthamide derivatives, we also identified the quinolone-2-carboxamides and 4-arylthiazole-2-carboxamides as potential MmpL3 inhibitors in which compounds 8i and 18b had MIC values of 9.97 and 9.82 μM, respectively. All four compounds retained their high activity against multidrug-resistant (MDR) and extensively drug-resistant (XDR) M. tb strains. It is worth noting that the two most active compounds 13c and 13d also exhibited the highest selective activity towards DS, MDR and XDR M. tb strains over mammalian cells [IC50 (Vero cells) ≥ 227 μM], indicating their potential lack of cytotoxicity. The four compounds were docked into the MmpL3 active site and were studied for their drug-likeness using Lipinski's rule of five.

TiO2 modified with a Ru(ii)-N′NN′ 8-hydroxyquinolyl complex for efficient gaseous photoreduction of CO2

A new rigid neutral Ru(ii) pincer complex [Ru(N′NN′)(ONO)] was synthesized from cationic [Ru(N′NN′)(MeCN)2Cl]Cl (N′NN′, 2,6-bis(N-benzyl-benzimidazol-2-yl)pyridine) and 4,8-dihydroxyquiniline-2-carboxylic acid (ONO). The X-ray diffraction analysis indicates that the Ru(ii) center adopts a slightly distorted octahedral geometry, in which the two benzyl moieties of the N′NN′ ligand are located on the same side of the coordination plane, defined by three N atoms of N′NN′ and the Ru(ii) center, and the dihedral angles of the benzyl group and the Ru(ii)-N′NN′ plane are 89.1° and 74.9°, respectively. Upon loading onto TiO2 nanoparticles (P25), this Ru(ii) complex exhibits an efficient CO2 photoreduction ability with CO/CH4 production activities of 26.6/17.2 μmol g-1 h-1 in a gaseous photocatalytic system containing CO2 and H2O vapor, which is much better than that of the pristine TiO2 nanoparticles. This result gives a good example of TiO2 nanoparticles loaded with the Ru(ii) pincer complex acting as a heterogeneous photocatalytic CO2 reduction system, which could facilitate the development of a more feasible artificial photosynthesis system.