81748-72-3

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINOMETHYL-QUINOLIN-8-OL serves as a crucial building block for the synthesis of a variety of drugs and biologically active molecules. Its molecular structure allows for easy incorporation into larger molecules, facilitating the development of new therapeutic agents.
Used in Antimalarial Applications:
5-AMINOMETHYL-QUINOLIN-8-OL is recognized for its potential antimalarial properties, making it a candidate for the development of new treatments against malaria, a disease that continues to impact global health.
Used in Antitubercular Applications:
5-AMINOMETHYL-QUINOLIN-8-OL also exhibits antitubercular potential, which positions it as a possible contributor to the creation of new drugs for combating tuberculosis, a persistent and challenging public health issue.
Used in Anticancer Applications:
5-AMINOMETHYL-QUINOLIN-8-OL's anticancer properties suggest its utility in the development of novel cancer therapies, offering hope for more effective treatments in oncology.
Used as a Fluorescent Probe:
In addition to its pharmaceutical applications, 5-AMINOMETHYL-QUINOLIN-8-OL is utilized as a fluorescent probe for monitoring cellular activities. This role is instrumental in various research and diagnostic applications, aiding in the study of cellular processes and functions.
The hydroxyl group present in 5-AMINOMETHYL-QUINOLIN-8-OL also offers the opportunity for further chemical modifications, which can enhance its biological activity and specificity, broadening its range of applications in the life sciences and medicine.

Upstream product

• 148-24-3 8-quinolinol 
• 1005143-73-6 5-azidomethyl-8-hydroxyquinoline 
• 4053-45-6 5-chloromethyl-8-hydroxyquinoline hydrochloride 
• 10136-57-9 5-(chloromethyl)quinolin-8-ol 

Downstream Products

• 1094606-80-0 3-(3,4-dihydroxyphenyl)-N-((8-hydroxyquinolin-5-yl)methyl)propanamide 
• 1094606-83-3 N⁽¹⁾-(3,4-bis(benzyloxy)phenethyl)-N⁽⁴⁾-((8-hydroxyquinolin-5-yl)methyl)succinamide 
• 1215290-49-5 5-((dibenzylamino)methyl)quinolin-8-ol 
• 1215290-52-0 N-((8-hydroxyquinolin-5-yl)methyl)-4-methylbenzamide 

Relevant academic research and scientific papers

In situ synthesis, electrochemical, surface morphological, UV–visible, DFT and Monte Carlo simulations of novel 5-substituted-8-hydroxyquinoline for corrosion protection of carbon steel in a hydrochloric acid solution

Two new organic compounds based on 8-hydroxyquinoline have been successfully synthesized, and characterized by FT-IR, 1H, 13C NMR and Elemental analysis. The synthesized compounds namely tert-butyl((8-hydroxyquinolin-5-yl)-methyl)-carbamate (BHQC) and Ethyl 3-(((8-hydroxyquinolin-5-yl)-methyl)-amino)-3-oxopropanoate (EHQP) are evaluated as corrosion inhibitors for carbon steel (CS) in 1 M HCl solution using electrochemical techniques, UV ? visible and SEM at 298 K. Electrochemical measurements showed that these organic compounds are mixed type inhibitors. The adsorption of both inhibitors on the carbon steel surface followed Langmuir adsorption isotherm. Furthermore, DFT calculations and Monte Carlo simulation were performed to theoretically establish the relationship between molecular structure and inhibition efficiency.

Quinoline tryptamine heterozygote and application thereof in preparation of medicines for treating Alzheimer's disease

The invention belongs to the technical field of medicines, and particularly relates to a quinoline tryptamine heterozygote and application thereof in preparation of medicines for treating and/or preventing Alzheimer's disease. Specifically disclosed are a compound represented by formula (I) and a pharmaceutically acceptable salt thereof. The quinoline tryptamine heterozygote disclosed by the invention has excellent oxygen free radical scavenging capacity, a protective effect on hydrogen peroxide induced SH-SY5Y cell oxidative damage, good blood-brain barrier passive dialysis capacity, an A[beta] self-aggregation inhibiting effect and metal ion chelating capacity, and is a multi-target anti-Alzheimer disease active molecule. The compound is expected to be used as a clinical medicine for treating and/or preventing Alzheimer's disease.

Synthesis and biological evaluation of indole-based UC-112 analogs as potent and selective survivin inhibitors

The anti-apoptotic protein survivin is highly expressed in cancer cells but has a very low expression in fully differentiated adult cells. Overexpression of survivin is positively correlated with cancer cell resistance to chemotherapy and radiotherapy, cancer cell metastasis, and poor patient prognosis. Therefore, selective targeting survivin represents an attractive strategy for the development of anticancer therapeutics. Herein, we reported the extensive structural modification of our recently discovered selective survivin inhibitor UC-112 and the synthesis of thirty-three new analogs. The structure-activity relationship (SAR) study indicated that replacement of the benzyloxy moeity in UC-112 with an indole moiety was preferred to other moieties. Among these UC-112 analogs, 10f, 10h, 10k, 10n showed the most potent antiproliferative activities. Interestingly, they were more potent against the P-glycoprotein overexpressing cancer cell lines compared with the parental cancer cell lines. Mechanistic studies confirmed that new analogs maintained their unique selectivity against survivin among the IAP family members. In vivo study using 10f in a human A375 melanoma xenograft model revealed that it effectively inhibited melanoma tumor growth without observable acute toxicity. Collectively, this study strongly supports the further preclinical development of selective survivin inhibitors based on the UC-112 scaffold.

The Synthesis and Characterization of s-Triazine-Cored Tripodal Structure and Its Salen/Salophen-Bridged Fe/Cr(III) Capped Complexes

A novel Schiff base compound was synthesized, and its complexation properties with Fe(III) and Cr(III) were investigated. Tripodal ligand was synthesized by the reaction of s-triazine and 4-hydroxybenzaldehyde. Then a Schiff base involving 8-hydroxyquinoline was synthesized by the reaction of 5-aminomethyl-8-hydroxyquinoline (QN) and 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD) in methanol/chloroform media. The obtained Schiff base (QN-TRIPOD) was then reacted with four trinuclear Fe(III) and Cr(III) complexes including tetradentate Schiff bases N,N′-bis(salicylidene)ethylenediamine (salenH2)/bis(salicylidene)-o-phenylenediamine (SalophenH2). The synthesized ligand and complexes were characterized by means of elemental analysis carrying out1H NMR, FTIR spectroscopy, thermal analyses, and magnetic susceptibility measurements. Finally, metal ratios of the prepared complexes were determined by using atomic adsorption spectrometry.

Structure-activity relationships and mechanism of action of antitumor bis 8-hydroxyquinoline substituted benzylamines

A series of twenty six 8-hydroxyquinoline substituted amines, structurally related to compounds 2 and 3, were synthesized to evaluate the effects of structural changes on antitumor activity and understand their mechanism of action. The studies were performed on a wide variety of cancer cell lines within glioma and carcinoma models. The results obtained from chemical models and biological techniques such as microarrays suggest the following hypothesis that a quinone methide intermediate which does not react with DNA but which gives covalent protein thiol adducts. Micro-array analysis showed that the drugs induce the expression of a variety of stress related genes responsible for the cytotoxic and cytostatic effects in carcinoma and glioblastoma cells respectively. The described analogues could represent new promising anti-cancer candidates with specific action mechanisms, targeting accessible thiols from specific proteins and inducing potent anti-cancer effects.

Synthesis and characterization of 5-substituted 8-hydroxyquinoline derivatives and their metal complexes

5-Aminomethyl-8-hydroxyquinoline (QN) was synthesized as a scaffold to generate dimers, trimers, and tetramer metalloquinolates. Starting from QN, a series of 5-substituted 8-hydroxyquinoline derivatives conjugated with small bioactive molecules were synthesized. Absorption and emission spectra indicate that these QN derivatives chelate well with metal ions, which may serve as a new platform to explore the applications of metalloquinolates for a variety of potential applications.