28027-17-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-7-methoxyquinoline-3-carboxylic acid is used as an active pharmaceutical ingredient for its potential antifungal and antibacterial properties. It can be formulated into medications to treat infections caused by fungi and bacteria, offering an alternative to existing treatments.
Used in Agrochemical Industry:
In the agrochemical industry, 4-Hydroxy-7-methoxyquinoline-3-carboxylic acid is used as a biocidal agent to protect crops from fungal and bacterial diseases. Its application can help improve crop yield and quality by reducing the impact of pathogens on plants.
Used in Research and Development:
4-Hydroxy-7-methoxyquinoline-3-carboxylic acid is utilized in research and development for the discovery of new drugs and agrochemicals. Its unique structure and properties make it a valuable compound for exploring novel therapeutic and protective agents against various pathogens.

InChI:InChI=1/C11H9NO4/c1-16-6-2-3-7-9(4-6)12-5-8(10(7)13)11(14)15/h2-5H,1H3,(H,12,13)(H,14,15)

Upstream product

• 63463-15-0 ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate 
• 536-90-3 m-Anisidine 
• 56881-19-7 Diethyl 2-<(3-methoxyphenylamino)methylene>malonate 

Downstream Products

• 82121-05-9 4-hydroxy-7-methoxyquinoline 
• 41957-77-1 3-cyclohexyl-2-cyclohexylimino-8-methoxy-2,3-dihydro-[1,3]oxazino[5,6-c]quinolin-4-one 
• 103040-78-4 7-methoxy-quinolin-4-ylamine 

Relevant academic research and scientific papers

Structure-activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (log K) and inhibition of β-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, log K values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (π) of the group X. The log K values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% β-hematin inhibitory activity (log BHIA50) was found to correlate with log K and either meta (σm) or para (σp) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that log K values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of β-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible.

Preparation of quinoline hexose analogs as novel chloroquine-resistant malaria treatments (1). Synthesis of 4-hydroxyquinoline-β-glucosides

Quinoline hexose analogs are expected to be useful as novel agents for treatment of chloroquine-resistant malaria. Here, we report preparation of 4-hydroxy quinoline-β-glucosides from anilines in 4 steps.

Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof

Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.

Structure-activity relationships for antiplasmodial activity among 7- substituted 4-aminoquinolines

Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)3NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7- bromo-AQs with diaminoalkane side chains [-HN(CH2)2NEt2, -HN(CH2)3NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC50s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC50s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC50s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC50s of 17-150 nM) and -resistant P. falciparum (IC50s of 90-3000 nM).

Thioquinolone compounds which have useful pharmaceutical activity

Disclosed is a thioquinolone derivative which exhibits highly selective antibacterial activity against Helicobacter pylori.