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Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-cinnoline is used as a building block for the synthesis of various pharmaceuticals due to its ability to contribute to the development of new drugs with potential therapeutic applications. Its presence in drug molecules can enhance their efficacy and selectivity, making it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Hydroxy-cinnoline is utilized as a key intermediate in the production of agrochemicals, including pesticides and herbicides. Its incorporation into these compounds can improve their effectiveness in controlling pests and weeds, thereby contributing to increased crop yields and agricultural productivity.
Used in Organic Synthesis:
4-Hydroxy-cinnoline is employed as a versatile intermediate in organic synthesis for the preparation of a wide range of organic compounds. Its reactivity and structural features make it suitable for various synthetic routes, facilitating the creation of complex molecules with diverse applications.
Used in Antitumor Research:
4-Hydroxy-cinnoline is used as a potential antitumor agent in cancer research. Its biological activities, including antioxidant and antibacterial properties, have been studied for their potential to inhibit tumor growth and contribute to cancer treatment strategies.
Used in Antioxidant and Antibacterial Applications:
Beyond its role in pharmaceutical and agrochemical development, 4-Hydroxy-cinnoline is also utilized in applications that leverage its antioxidant and antibacterial properties. These uses can be found in various industries, such as cosmetics, food preservation, and material science, where its ability to combat oxidative stress and inhibit microbial growth is highly valued.

Upstream product

• 5152-83-0 cinnolin-4-ylamine 
• 53512-17-7 4-Hydroxy-cinnoline-3-carboxylic acid 
• 1066-54-2 trimethylsilylacetylene 
• 613-89-8 2-Aminoacetophenone 
• 551-93-9 2-aminoacetophenone 
• 143232-59-1 4-amino-3-cinnolinecarboxylic acid 
• 615-43-0 2-iodophenylamine 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 

Downstream Products

• 5155-71-5 2-benzyl-4-oxo-1,4-dihydro-cinnolinium betaine 
• 611-35-8 4-chloroquinoline 
• 727375-11-3 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-cinnolin-4-one 
• 173415-12-8 (4-chloro-3-cinnolinyl)-2-methoxyphenylmethanol 
• 173415-29-7 (4-Chloro-cinnolin-3-yl)-(2-methoxy-phenyl)-methanone 
• 173415-11-7 (4-chloro-3-cinnolinyl)phenylmethanol 
• 173415-28-6 (4-Chloro-cinnolin-3-yl)-phenyl-methanone 
• 82452-99-1 4-chloro-3-iodocinnoline 
• 173415-33-3 4-chloro-3-methylcinnoline 
• 5152-83-0 cinnolin-4-ylamine 
• 297134-05-5 8-(4'-methoxyphenyl)-4-(4'-trifluoromethylphenyl)-3-trimethylsilylcinnoline 
• 297134-08-8 4-(4'-methoxyphenyl)-8-(4'-trifluoromethylphenyl)-3-trimethylsilylcinnoline 
• 297134-06-6 8-(2'-thienyl)-4-(4'-trifluoromethylphenyl)-3-trimethylsilylcinnoline 
• 297134-10-2 4-(4'-methoxyphenyl)-8-(3'-nitrophenyl)-3-trimethylsilylcinnoline 

Relevant academic research and scientific papers

Novel 4-(1H-1,2,3-triazol-4-yl)methoxy)cinnolines as potent antibacterial agents: Synthesis and molecular docking study

A new series of cinnoline-1,2,3-triazole derivatives were designed and synthesized by adopting Cu(1) catalyzed regeoselective1,3-dipolar cycloaddition reaction of terminal alkyne and azide. The in vitro antibacterial activity of all these compounds revealed that compounds 9d, 10a, 10b, and 10c are more potent antibacterial agents. Among the series, compound 4-(3-(4-((cinnolin-4-yloxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)morpholine (10b) exhibited the most potent antibacterial activity against all tested gram-positive and gram-negative bacterial strains. Furthermore, molecular docking studies were also performed to understand the binding interactions of the most active analogs 9d, 10a, 10b, and 10c with Elastase of Pseudomonas aeruginosa (PDB: 1U4G). The results indicated that these classes of compounds have potential antibacterial activity, especially the compound 10b may serve as a promising antibacterial lead compound that could be further optimized for the further development of antibacterial drugs.

TOLL-LIKE RECEPTOR 8 (TLR8)-SPECIFIC ANTAGONISTS AND METHODS OF MAKING AND USES THEREOF

Toll-like receptor 8 (TLR8)-specific inhibitors and methods of using the same in individuals having an autoimmune disease or an inflammatory disorder.

4-Aminoquinolone piperidine amides: Noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity

4-Aminoquinolone piperidine amides (AQs) were identified as a novel scaffold starting from a whole cell screen, with potent cidality on Mycobacterium tuberculosis (Mtb). Evaluation of the minimum inhibitory concentrations, followed by whole genome sequencing of mutants raised against AQs, identified decaprenylphosphoryl-β-d-ribose 2′-epimerase (DprE1) as the primary target responsible for the antitubercular activity. Mass spectrometry and enzyme kinetic studies indicated that AQs are noncovalent, reversible inhibitors of DprE1 with slow on rates and long residence times of ～100 min on the enzyme. In general, AQs have excellent leadlike properties and good in vitro secondary pharmacology profile. Although the scaffold started off as a single active compound with moderate potency from the whole cell screen, structure-activity relationship optimization of the scaffold led to compounds with potent DprE1 inhibition (IC50 10 nM) along with potent cellular activity (MIC = 60 nM) against Mtb.

Synthesis of 4,8-diarylcinnolines and quinazolines with potential applications in nonlinear optics. Diazines. Part 28

New 4,8-diarylbenzodiazines have been synthesized using cross-coupling reactions and regioselective metalation at the peri-position C8 of the benzene moiety of various cinnolines and quinazolines. Some of these compounds have been tested to assess their nonlinear optical properties. (C) 2000 Elsevier Science Ltd.

Solid-phase synthesis of substituted cinnolines by a Richter type cleavage protocol

Starting from triazene bound ortho-halo arenes on a solid support, palladium-catalyzed alkynylations and subsequent cleavage reactions under acidic conditions give rise to ortho-alkynylaryldiazonium salts, which in turn undergo cyclization to afford substituted 4-halo- and 4- hydroxycinnolines in moderate to good yields. The method is applicable to automated synthesis.

Synthesis, structures and biological activity of some 4-amino-3-cinnoline-carboxylic acid derivatives. Part 2

6,7,8-Substituted 4-amino-3-cinnolinecarboxylic acids 1 were condensed with amines to the corresponding 4-amino-3-cinnolinecarboxamides 7, 8. A variety of pharmacological tests showed a significant CNS activity of some new amides. Decarboxylation of 4-amino-3-cinnolinecarboxylic acids 1 yielded the corresponding 4-aminocinnolines 4 and alkaline hydrolysis of 1 gave 4-oxo-3-cinnolinecarboxylic acids 2. The acids 1 were converted into pyrimido[5,4-c]cinnolines 6 on two ways of synthesis.

Method for preparing 4-hydroxycinnolines in a pH controlled system

In the preparation of a 4-hydroxycinnoline wherein the diazonium salt of a 2-aminoacetophenone in aqueous solution is allowed to undergo cyclocondensation, the improvement that comprises maintaining the pH of the solution between about 4.0 and 8.5 during the cyclocondensation.