15151-57-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dihydroxy-3-nitroquinoline is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic effects.
Used in Organic Synthesis:
In the field of organic synthesis, 2,4-Dihydroxy-3-nitroquinoline is used as a building block for creating various organic compounds, highlighting its utility in chemical research and the creation of novel molecules.
Used in Antimicrobial Applications:
2,4-Dihydroxy-3-nitroquinoline is used as an antimicrobial agent for its potential to combat infections by inhibiting the growth of microorganisms, making it a candidate for further exploration in infectious disease treatment.
Used in Anti-Inflammatory Applications:
As an anti-inflammatory agent, 2,4-Dihydroxy-3-nitroquinoline is utilized to reduce inflammation, a property that can be beneficial in the treatment of conditions characterized by excessive immune responses.
Used in Fluorescent Dye Applications:
In biological imaging, 2,4-Dihydroxy-3-nitroquinoline is used as a fluorescent dye, capitalizing on its optical properties to visualize cellular and molecular structures, aiding in research and diagnostics.

InChI:InChI=1/C9H6N2O4/c12-8-5-3-1-2-4-6(5)10-9(13)7(8)11(14)15/h1-4H,(H2,10,12,13)

Upstream product

• 70254-44-3 2,4-dihydroxyquinoline 
• 70254-43-2 4-Hydroxy-2-quinolone 
• 172469-70-4 5-ethyl-4-hydroxy-3-nitropyridin-2(1H)-one 
• 62-53-3 aniline 
• 621-10-3 N,N'-diphenylmalonamide 

Downstream Products

• 132521-66-5 2,4-dichloro-3-nitroquinoline 
• 259178-25-1 1-[2-(1-benzyl-piperidin-4-yl)-ethyl]-4-chloro-1H-imidazo[4,5-c]quinoline 
• 259178-95-5 tert-butyl 4-[2-(4-phenoxy-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-1-piperidinecarboxylate 
• 259178-96-6 1-[2-(1-benzyl-4-piperidyl)ethyl]-4-phenoxy-1H-imidazo[4,5-c]quinoline 
• 259178-32-0 tert-butyl 4-[2-(4-chloro-2-phenyl-1H-imidazo[4,5-c]-quinolin-1-yl)ethyl]-1-piperidinecarboxylate 
• 144875-48-9 resquimod 
• 936544-96-6 tert-butyl (4-(((2-chloro-3-nitroquinolin-4-yl)amino)methyl)benzyl)carbamate 
• 936544-97-7 tert-butyl (4-(((3-amino-2-chloroquinolin-4-yl)amino)methyl)benzyl)carbamate 
• 1258457-59-8 1-[[4-(aminomethyl)phenyl]methyl]-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine 
• 1508303-97-6 5-chloro-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-98-7 5-iodo-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 133860-75-0 2-chloro-N⁴-(2-methylpropyl)-3-nitroquinoline-4-amine 
• 133860-76-1 2-chloro-N⁴-(2-methylpropyl)quinoline-3,4-diamine 
• 1508303-93-2 2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 

Relevant academic research and scientific papers

Structure-activity relationships of 4-hydroxy-3-nitroquinolin-2(1H)- ones as novel antagonists at the glycine site of N-methyl-D-aspartate receptors

A series of 4-hydroxy-3-nitroquinolin-2(1H)-ones (HNQs) was synthesized by nitration of the corresponding 2,4-quinolinediols. The HNQs were evaluated as antagonists at the glycine site of NMDA receptors by inhibition of [3H]DCKA binding to rat brain membranes. Selected HNQs were also tested for functional antagonism by electrophysiological assays in Xenopus oocytes expressing either 1a/2C subunits of NMDA receptors or rat brain AMPA receptors. The structure-activity relationships (SAR) of HNQs showed that substitutions in the 5-, 6-, and 7-positions in general increase potency while substitutions in the 8-position cause a sharp reduction in potency. Among the HNQs tested, 5,6,7-trichloro HNQ (8i) was the most potent antagonist with an IC50 of 220 nM in [3H]DCKA binding assay and a K(b) of 79 nM from electrophysiological assays. Measured under steady-state conditions HNQ 8i is 240-fold selective for NMDA over AMPA receptors. The SAR of HNQs was compared with those of 1,4-dihydroquinoxaline-2,3-diones (QXs) and 1,2,3,4-tetrahydroquinoline-2,3,4-trione 3-oximes (QTOs). In general, HNQs have similar potencies to QXs with the same benzene ring substitution pattern but are about 10 times less active than the corresponding QTOs. HNQs are more selective for NMDA receptors than the corresponding QXs and QTOs. The similarity of the SAR of HNQs, QXs, and QTOs suggested that these three classes of antagonists might bind to the glycine site in a similar manner. With appropriate substitutions, HNQs represent a new class of potent and highly selective NMDA receptor glycine site antagonists.

Design, synthesis, and anticonvulsant evaluation of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives

The novel group of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives was designed as potential anticonvulsants using GABA pharmacophore and corresponding heterocyclic moieties. A number of compounds of this group were synthesized and studied in the maximum electroshock seizure (MES) test and in the model of primary-generalized convulsions caused by subcutaneous pentylenetetrazole (scPTZ) in mice. The most active compound in the MES test was found to be 1a (N-(3-nitrocoumarin-4-yl)-4-aminobutyric acid) at a dose range of 60–80 mg/kg that increased the number of survived animals up to 60% in comparison with the control group, whose survival rate was 10%. Compounds 1d (N-(3,6-dinitrocoumarin-4-yl)-4-amino-butyric acid methyl ester) at doses of 10–40 mg/kg and 3a (N-(3-nitro-2-oxo-1,2-dihydroquinolin-4-yl)-4-amino-butyric acid methyl ester) at a dose of 12.5 mg/kg had the most pronounced anticonvulsant effect in scPTZ test. [Figure not available: see fulltext.].

Imidazo quinoline substituted phosphate agonist as well as preparation method and application thereof

The invention relates to an imidazo quinoline substituted phosphate agonist as well as a preparation method and an application thereof. Specifically, the compound disclosed by the invention has a structure as shown in a formula (I), and the definitions of all groups and substituent groups are described in the specification. The invention also discloses a preparation method of the compound and the application of the compound as a TLR agonist.

IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF

Provided in the present disclosure are imidazoquinoline-type compounds, methods for their preparation, pharmaceutical compositions thereof and their use, wherein the imidazoquinoline-type compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach

Imiquimod (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine) is efficacious in topical therapy for certain types of skin cancers. Structurally similar EAPB0203 (N-methyl-1-(2-phenethyl)imidazo[1,2-a]quinoxalin-4-amine) has been shown higher in vitro potency than imiquimod. Besides, triazole, oxadiazole, and thiadiazole rings are privileged building blocks in drug design. A series of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole and [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-thiadiazole derivatives were therefore synthesized by incorporation of these rings into the structure of EAPB0203 and assessed their antiproliferative effects against various cancer cell lines. The 1,3,4-oxadiazole derivatives demonstrated the superior effectiveness compared to imiquimod and EAPB0203. Our findings highlight the excellent potential of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as anticancer agents.

TLR7/8 AGONISTS AND LIPOSOME COMPOSITIONS

The present disclosure relates to a method of loading a toll like receptor (TLR)7/8 agonist into a liposome using remote loading and a kit of parts suitable for the loading of a TLR7/8 agonist into a liposome by said method. The present disclosure further relates to a liposome comprising a salt of a TLR7/8 agonist in the liposome interior and to the use of said liposome for stimulation of an immune response and/or treatment of a clinical condition. Finally, the present disclosure relates to a TLR7/8 agonist which is suitable for being remotely loaded into a liposome.

PEPTIDE-BASED VACCINES, METHODS OF MANUFACTURING, AND USES THEREOF FOR INDUCING AN IMMUNE RESPONSE

The present disclosure relates to novel peptide-based vaccines, methods of manufacturing the novel peptide-based vaccines and uses thereof for delivering peptide antigens to induce an immune response, and in particular a T cell response to a subject.

LOCALLY ACTING TOLL-LIKE RECEPTOR 7 (TLR7) AND/OR TLR8 AGONIST IMMUNOTHERAPY COMPOUNDS AND THEIR USES

Provided in the present disclosure are immunotherapy compounds, pharmaceutical compositions thereof and their use, wherein the immunotherapy compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

Efficacy of TLR7 agonistic imidazoquinoline as immunochemotherapeutic agent against P. Berghei ANKA infected rodent host

Malaria is a serious disease and is one of the most alarming public health issues. Plasmodium is being resistant to various antimalarials including Chloroquine (CQ) which was the first-line therapy for malaria treatment. WHO recommended several combination therapies but declining efficacy was reported to many of these therapies. Despite a great amount of research, efficient malaria vaccine still seems to be a distant dream. Immunochemotherapy could be an alternate strategy to deal with malaria. Based on the differential activity of various cytokines in the pathogenesis of and protection against malaria, the efficacy of highly active TLR7 agonistic imidazoquinoline (BBIQ) in combination with a suboptimal dose of CQ against P. berghei ANKA (PbA) in vivo was investigated. In mice treated with CQ alone, parasite appeared on Day 17 and all mice of this group died by Day 21. Whereas, mice treated with BBIQ along with CQ exhibited no appearance of parasite till Day 23. Frequencies of T cells (CD3+, CD4+and CD8+) and T regulatory cells (CD4+, CD25 +and FoxP3+) were found to be lower in brain of BBIQ + CQ treated mice as compared to BBIQ alone and CQ alone treated mice on Day 10. Inhibition of infiltration of inflammatory T cells and activation of T helper and T cytotoxic cells against the parasite was observed in the mice treated with this combination therapy. Serum levels of IFN-γ and IL-12 were found to be higher on same day in mice treated with BBIQ + CQ which revealed the generation of strong Th1 immune response in mice against the infection. Overall, TLR7 agonist acted as an efficient partner when combined with potent antimalarial drug.

ALKYL CHAIN MODIFIED IMIDAZOQUINOLINE TLR7/8 AGONIST COMPOUNDS AND USES THEREOF

Disclosed are alkyl chain modified 1H-imidazoquinoline compounds, derivatives and analogs thereof, as Toll-like receptor-7 and -8 agonists for enhancing immune responses. Also provided are methods of making pharmaceutical compositions containing these compounds. The present disclosure also describes methods of use for the alkyl chain modified 1H-imidazoquinoline compounds, derivatives and analogs thereof, and pharmaceutical compositions containing these compounds for the treatment of disease in a subject.