81748-72-3

Basic information

• Product Name: 5-AMINOMETHYL-QUINOLIN-8-OL
• Synonyms: 5-AMINOMETHYL-QUINOLIN-8-OL;AKOS BC-0045
• CAS NO: 81748-72-3
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• Mol File: 81748-72-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-AMINOMETHYL-QUINOLIN-8-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINOMETHYL-QUINOLIN-8-OL(81748-72-3)
• EPA Substance Registry System: 5-AMINOMETHYL-QUINOLIN-8-OL(81748-72-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 81748-72-3(Hazardous Substances Data)

Usage

General Description

5-AMINOMETHYL-QUINOLIN-8-OL is a chemical compound that contains a quinoline ring with an aminoethyl group attached to the 5-position and a hydroxyl group at the 8-position. It is used in the pharmaceutical industry as a building block for the synthesis of various drugs and biologically active molecules. 5-AMINOMETHYL-QUINOLIN-8-OL is known for its potential antimalarial, antitubercular, and anticancer properties and is also used as a fluorescent probe for monitoring cellular activities. The aminoethyl group allows for the compound to be easily incorporated into larger molecules, making it a valuable tool for drug discovery and development. Additionally, the hydroxyl group provides the potential for further modifications to enhance its biological activity and specificity.

Upstream product

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

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 articles and documents

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.

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.

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.