578-67-6

Usage

Uses

Used in Pharmaceutical Industry:
5-Hydroxyquinoline is used as an internal standard for measuring morphine concentration in serum or plasma. Its stability and compatibility with the testing process make it an ideal choice for accurate and reliable results.
Used in Chemical Research:
As a lipophilic chelator, 5-Hydroxyquinoline is employed to decrease the rate of deoxygenation in various chemical reactions. This property allows researchers to control reaction rates and study the effects of different conditions on the reaction outcomes.
Used in Analytical Chemistry:
Due to its chemical properties, 5-Hydroxyquinoline is also utilized in analytical chemistry for the detection and quantification of specific substances. Its ability to form complexes with various elements makes it a valuable tool in the identification and measurement of target compounds.

InChI:InChI=1/C9H7NO/c11-9-5-1-4-8-7(9)3-2-6-10-8/h1-6,11H

Upstream product

• 611-34-7 5-Aminoquinoline 
• 23261-58-7 quinoline-5-sulfonic acid 
• 87707-14-0 1a,7b-dihydrooxireno[2,3-f]quinoline 
• 91-22-5 quinoline 
• 333383-80-5 3-(N-3-hydroxyphenyl-N-p-tosylpropionaldehyde) 
• 1236162-22-3 C₉H₆ClNO 
• 607-34-1 5-nitroquinoline 
• 394-69-4 5-fluoroquinoline 
• 591-27-5 m-Hydroxyaniline 
• 3743-29-1 N-(3-hydroxyphenyl)-4-methylbenzenesulfonamide 
• 177734-78-0 5-trifluoromethanesulphonyloxyquinoline 
• 81336-58-5 5-Quinolyl benzoate 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 4964-71-0 5-bromoquinoline 

Downstream Products

• 81336-58-5 5-Quinolyl benzoate 
• 6931-19-7 5-methoxyquinoline 
• 611-34-7 5-Aminoquinoline 
• 31570-97-5 NCI 134652 
• 856083-17-5 8-iodo-quinolin-5-ol 
• 61468-43-7 5-hydroxy-1,2,3,4-tetrahydroquinoline 
• 741691-58-7 5-(4-nitrophenoxy)quinoline 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 
• 863487-50-7 [4-(quinolin-5-yloxymethyl)-phenyl]-carbamic acid tert-butyl ester 
• 145679-40-9 5-[(2R)-oxiranylmethoxy]-quinoline 
• 793670-97-0 6-allyl-5-benzyloxy-quinoline 
• 793670-98-1 3-(5-benzyloxy-quinolin-6-yl)-propane-1,2-diol 
• 941579-39-1 C₂₁H₂₀BrNO₃ 
• 793671-02-0 3,4-dihydro-2H-pyrano(2,3-f)quinolin-3-yl-4-methylbenzenesulfonate 

Relevant academic research and scientific papers

One-step hydroxylation of aryl and heteroaryl fluorides using mechanochemistry

Simple use of KOH allows the direct F to OH exchange of aromatic and heteroaromatic substrates under mechanochemical conditions. The reaction is performed in the absence of solvent with potassium hydroxide as OH source. As a result, this approach is both more atom economical and environmentally friendly than previously described methods for this transformation.

Radical-anion coupling through reagent design: hydroxylation of aryl halides

The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described. Key to the success of this approach was the identification of a reducing oxime anion which can interact and couple with open-shell aryl radicals. Experimental and computational studies support the proposed radical-nucleophilic substitution chain mechanism.

Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines

Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.

Application of quebrachitol in hydrolysis reaction of copper-catalyzed aryl halide

The invention belongs to the technical field of drug synthesis, and provides application of quebrachitol in a hydrolysis reaction of a copper-catalyzed aryl halide. According to the hydrolysis reaction, copper serves as a catalyst, quebrachitol serves as a ligand, and the hydrolysis reaction is carried out on the aryl halide. The invention further provides a catalytic system of the hydrolysis reaction of the aryl halide. The reaction system comprises the copper catalyst, the quebrachitol, alkali and water, and the system is environmentally friendly and is suitable for industrial application.

Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water

A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.

NOVEL QUINOLINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS FOR PREVENTING OR TREATING CANCER CONTAINING THE SAME

The present invention refers to an excellent cancer antiproliferative potency relative to the quinoline compounds, a pharmaceutically acceptable salt, or hydrate and, number of active ingredient containing bath method and pharmaceutical composition for the prevention or treatment of cancer disease relates to search, said present invention according to compound, a pharmaceutically acceptable salt thereof, or hydrate number and number and mutant kinase protein kinase activity number of excellent cancer billion billion number activity and thus, new anticancer number is useful as the effective component can be. (by machine translation)

Synthesis of Complex Phenols Enabled by a Rationally Designed Hydroxide Surrogate

The conversion of aryl halides to phenols under mild reaction conditions is a longstanding and formidable challenge in organic chemistry. Herein, we report the rational design of a broadly applicable Pd-catalyzed method to prepare phenols with benzaldehyde oxime as a hydroxide surrogate. These reactions occur under mildly basic conditions and enable the late-stage hydroxylation of several functionally-dense drug-like aryl halides.

Reagent Design and Ligand Evolution for the Development of a Mild Copper-Catalyzed Hydroxylation Reaction

Parallel synthesis and mass-directed purification of a modular ligand library, high-throughput experimentation, and rational ligand evolution have led to a novel copper catalyst for the synthesis of phenols with a traceless hydroxide surrogate. The mild reaction conditions reported here enable the late-stage synthesis of numerous complex, druglike phenols.

Design and synthesis of new 2-anilinoquinolines bearing N-methylpicolinamide moiety as potential antiproliferative agents

A series of new 2-anilinoquinolines 6a–o possessing the substantial N-methylpicolinamide motif at C5 has been designed and synthesized as sorafenib analogs. The antiproliferative activities of the target compounds were preliminarily appraised against a panel of three human cancer cell lines (MCF-7, SK-BR3, and HCT116), and a selected array was further tested over a panel of approximately 60 cancer cell lines at NCI at 10?μM concentration. Interestingly, compounds 6c, 6d, 6j, 6k, and 6l showed promising selective anticancer activities (growth inhibition >80%) toward certain cancer cells at 10?μM testing dose. Compounds 6d and 6j were advanced to five-dose testing mode to determine their GI50 values and compared with our previously reported ureidoquinoline B and sorafenib as reference compounds. The 4-chloro-3-trifluoromethylaniline derivative 6j manifested superior potency than both compound B and sorafenib over eleven and eight cell lines, respectively. It showed GI50 values of 0.36, 0.66, 0.68, and 0.60?μM against the breast MDA-MB-468, renal A498, and melanoma SK-MEL-5 and UACC-62 cell lines, respectively. Moreover, both 6d and 6j exerted low cytotoxic effects against HFF-1 normal cell line. Furthermore, compounds 6d and 6j were tested against both B-RafV600E and C-Raf kinases and displayed modest inhibitory activities, which were justified by molecular docking study. Compound 6j could serve as a promising candidate for further development of potent anticancer chemotherapeutics.

Novel 5-substituted-2-anilinoquinolines with 3-(morpholino or 4-methylpiperazin-1-yl)propoxy moiety as broad spectrum antiproliferative agents: Synthesis, cell based assays and kinase screening

A series of new 2-anilinoquinolines possessing 3-(morpholino or 4-methylpiperazin-1-yl)propoxy moiety at C5 of quinoline has been designed and synthesized as potential anticancer agents. Their antiproliferative activities were evaluated against a panel of 60 cancer cell lines at NCI and compared with gefitinib as a reference compound. Most of the tested compounds displayed potent and broad spectrum antiproliferative activities. Compounds 7d, 7f and 7g showed strong inhibitory and lethal effects at 10?μM concentration. Moreover, they manifested superior potencies and efficacies than gefitinib across the most tested cell lines. Compound 7d, with 4-chloro-3-trifluoromethylphenyl group, proved to be the most potent and efficacious derivative in this series, with mean GI50and TGI values of 1.62?μM and 3.47?μM, respectively. Kinase screening of 7d against a panel of 47 oncogenic kinases revealed its selective inhibitory effect (96% inhibition) towards TrkA kinase. Furthermore, the most potent compounds showed low cytotoxic effects against HFF-1 normal cell line.