The Reaction of Aldehydes and Aromatic Amines with 8-Quinolinol

Phillips, J. P.; Keown, Robert W.; Fernaǹdo, Quintus

doi:10.1021/ja01113a048

Cited by 21 publications

(13 citation statements)

References 2 publications

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“…Compound 1 (M.W. 489.59) is a new compound synthesized in the laboratory using the previously reported method (Phillips et al, 1953) and the structure was confirmed by NMR. The sources of the compounds 2 (M.W.…”

Section: Methodsmentioning

confidence: 99%

Characterization of 8-hydroxyquinoline derivatives containing aminobenzothiazole as inhibitors of dengue virus type 2 protease in vitro

2013

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Four serotypes of Dengue virus (DENV1–4), mosquito-borne members of Flaviviridae family cause frequent epidemics causing considerable morbidity and mortality in humans throughout tropical regions of the world. There is no vaccine or antiviral therapeutics available for human use. In a previous study, we reported that compounds containing the 8-hydroxyquinoline (8-HQ) scaffold as inhibitors of West Nile virus serine protease. In this study, we analyzed potencies of some compounds with (8-HQ)-aminobenzothiazole derivatives for inhibition of DENV2 protease in vitro. We identified analogs 1–4 with 2-aminothiazole or 2-aminobenzothiazole scaffold with submicromolar potencies (IC50) in the in vitro protease assays. The kinetic constant (Ki) for the most potent 8-HQ-aminobenzothiazoleinhibitor (compound 1) with an IC50 value of 0.91 ± 0.05 µM was determined to be 2.36 ± 0.13 µM. This compound inhibits the DENV2 NS2B/NS3pro by a competitive mode of inhibition.

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Section: Methodsmentioning

confidence: 99%

Characterization of 8-hydroxyquinoline derivatives containing aminobenzothiazole as inhibitors of dengue virus type 2 protease in vitro

2013

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“…The aromatic methyl group resonated at 2.49 as singlet. The 1 H NMR spectral data ( Table 1) and mass fragmentation pattern determined the structure of this Mannich base as 7-[ -(2 -Methylanilino) benzyl]-8-hydroxyquinoline, (1, Figure 1), the preparation of which has been reported earlier [15,16].…”

Section: General Procedures For the Preparation Of Mannish Basesmentioning

confidence: 63%

Synthesis of Mannich Bases of 8-Hydroxyquinoline

Siddiqi

Faizi

Naz

et al. 2015

J. Basic Appl. Sci.

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In search of new potential therapeutic agents, 8-Hydroxyquinoline which is a highly active antifungal and antibacterial agent was subjected to Mannich reaction. Different combinations of aromatic aldehyde and aromatic amines were used for Mannich reaction on 8-Hydroxyquinoline from which one new 7-[-(anilino)-3',4'-dimethoxybenzyl]-8hydroxyquinoline (3) and two known Mannich bases (1,2) were obtained.

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“…Higher molecular diversity and the formation of a new chiral carbon centre could be achieved by the use of Betti-3CR: treatment of several (aromatic) aldehydes with primary amines then 8-HQ, 5-nitro-, or 5-chloro-8-HQ. The application of Mannich-3CR of simple formaldehyde and secondary amines as an iminium source for addition, is highlighted for biological utilization [ 2 , 3 ]. Based on previously published biological studies, the structurally modified 8-HQs exert two main activities depending on the C-7 function and substitution pattern of the mother compound, 8-HQ.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytoprotective Characterization of 8-Hydroxyquinoline Betti Products

Kanizsai¹,

Madácsi²,

Hackler³

et al. 2018

Molecules

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The 8-hydroxyquinoline pharmacophore scaffold has been shown to possess a range of activities as metal chelation, enzyme inhibition, cytotoxicity, and cytoprotection. Based on our previous findings we set out to optimize the scaffold for cytoprotective activity for its potential application in central nervous system related diseases. A 48-membered Betti-library was constructed by the utilization of formic acid mediated industrial-compatible coupling with sets of aromatic primary amines such as anilines, oxazoles, pyridines, and pyrimidines, with (hetero)aromatic aldehydes and 8-hydroxiquinoline derivatives. After column chromatography and re-crystallization, the corresponding analogues were obtained in yields of 13–90%. The synthesized analogs were optimized with the utilization of a cytoprotection assay with chemically induced oxidative stress, and the most active compounds were further tested in orthogonal assays, a real time cell viability method, a fluorescence-activated cell sorting (FACS)-based assay measuring mitochondrial membrane potential changes, and gene expression analysis. The best candidates showed potent, nanomolar activity in all test systems and support the need for future studies in animal models of central nervous system (CNS) disorders.

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The Reaction of Aldehydes and Aromatic Amines with 8-Quinolinol

Cited by 21 publications

References 2 publications

Characterization of 8-hydroxyquinoline derivatives containing aminobenzothiazole as inhibitors of dengue virus type 2 protease in vitro

Characterization of 8-hydroxyquinoline derivatives containing aminobenzothiazole as inhibitors of dengue virus type 2 protease in vitro

Synthesis of Mannich Bases of 8-Hydroxyquinoline

Synthesis and Cytoprotective Characterization of 8-Hydroxyquinoline Betti Products

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