Anti‐SARS‐CoV‐2 Inhibitory Profile of New Quinoline Compounds in Cell Culture‐Based Infection Models

Herrmann, Lars; Hahn, Friedrich; Wangen, Christina; Marschall, Manfred; Tsogoeva, Svetlana B.

doi:10.1002/chem.202103861

Cited by 8 publications

(8 citation statements)

References 24 publications

(22 reference statements)

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“…Selium et al reported that the quinoline‐triazole moieties compound 111 showed potential antiviral properties against severe acute respiratory syndrome coronavirus‐2 (SARS‐COV‐2) with IC 50 0.060 mM value compared with the hydroxychloroquine and chloroguine as reference standard drug (Seliem et al, 2021). Herrmann et al reported the quinoline‐morpholine hybrid compound 112 as ( Caco‐2 ) cell culture‐based inhibitory action against SARS‐CoV‐2 with half maximal effective concentration (EC 50 ) value 15.9 ± 14.1 μM (Herrmann et al, 2022). The structure for the quinolone derivatives that showed miscellaneous activities listed in Figure 12.…”

Section: Biological Activitiesmentioning

confidence: 99%

Quinoline‐derivatives as privileged scaffolds for medicinal and pharmaceutical chemists: A comprehensive review

et al. 2022

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The quinoline scaffolds are privileged for their numerous biological activities in the pharmaceutical field. This moiety constitutes a well‐known space in several marketed preparations. The quinoline scaffolds gained attention in modern days being an important chemical moiety in the identification, designing, and synthesis of novel potent derivatives. The current review is developed to shine the light on critical and significant insights on the quinoline derivatives possessing diverse biological activities such as analgesic, anti‐inflammatory, antialzheimer, anti‐convulsant, anti‐oxidant, antimicrobial, anti‐cancer activities and so on. A detailed summary of quinoline ring from its origin to the recent advancements regarding its synthesis, green chemistry approaches, patented methods, and its marketed drugs is presented in the review. We attempted to review the literature compiling the critical information that has potential to encourage fellow researchers and scientists for the design and development of quinoline scaffold based active molecules that have improved therapeutic performance along with profound pharmacological properties.

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Section: Biological Activitiesmentioning

confidence: 99%

Quinoline‐derivatives as privileged scaffolds for medicinal and pharmaceutical chemists: A comprehensive review

et al. 2022

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“…In general, triazole hybrids display a range of biological activities, such as antibacterial [5], antitubercular [6], antiviral [7], antimalarial, and anti-inflammatory effects. This has led to significant interest in developing novel compounds based on the 1,2,3-triazole scaffold with potential therapeutic applications.…”

Section: Introductionmentioning

confidence: 99%

(2R, 4S, 5S) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1H-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Kuan

Xie

Guo

et al. 2023

Molbank

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1,2,3-triazole pharmacophore is a widely recognized motif used for a variety of applications, including drug discovery, chemical biology, and materials science. We herein report the synthesis of a derivative of azidothymidine (AZT), which was combined with the 7-chloro quinoline scaffold through a 1,4-disubstituted 1,2,3-triazole. The chemical structure of the new molecule was fully characterized by Fourier transform infrared (FTIR) spectroscopy, proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC) distortionless enhancement by polarization transfer (DEPT), correlation spectroscopy (1H-1H-COSY), ultraviolet (UV) spectroscopy, and high-resolution mass spectrometry (HRMS). Computational studies were used to predict the interaction of the synthesized compound with HIV reverse transcriptase, a target of relevance for developing new therapeutics against AIDS. The drug-likeness of the compound was also investigated by computing the physico-chemical properties that are important for the pharmacokinetic profile.

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“…Intensive drug discovery efforts for developing new antimalarial/antiviral drugs or modifying existing agents are ongoing (Figure 1b) [5]. Molecular hybridization is a well-established strategy that combines two compounds or their moieties into a new, single hybrid molecule [6].…”

Section: Introductionmentioning

confidence: 99%

“…Considering the physicochemical and pharmacological features of known scaffolds, it is possible to expand drug libraries of homologous molecular hybrids through the fusion (usually via a covalent linker) of two drugs [7]. Therefore, a well-known scaffold, 1,2,3-triazole [8], appears frequently in medicinal compounds, and many covalently linked triazole hybrids exhibit diverse biological activities, such as antibacterial [9], antitubercular [10], anti-viral [5], antimalarial [11], and anti-inflammatory effects (Figure 1c-f).…”

Section: Introductionmentioning

confidence: 99%

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2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde

Yun

Xie

et al. 2022

Molbank

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The 1,2,3-triazole ring system can be easily obtained by copper-catalyzed click reaction of azides with alkynes. 1,2,3-Triazole exhibits a myriad of biological activities, including antimalarial, antibacterial, and antiviral activities. We herein reported the synthesis of quinoline-based [1,2,3]-triazole hybrid via Cu(I)-catalyzed click reaction of 4-azido-7-chloroquinoline with alkyne derivative of 2-bromobenzaldehyde. The compound was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV), and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro against two different normal cell lines. Preliminary studies attempted to evaluate its interaction with Delta RBD of spike protein of SARS-CoV-2 by bio-layer interferometry. Finally, the drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties.

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Anti‐SARS‐CoV‐2 Inhibitory Profile of New Quinoline Compounds in Cell Culture‐Based Infection Models

Cited by 8 publications

References 24 publications

Quinoline‐derivatives as privileged scaffolds for medicinal and pharmaceutical chemists: A comprehensive review

Quinoline‐derivatives as privileged scaffolds for medicinal and pharmaceutical chemists: A comprehensive review

(2R, 4S, 5S) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1H-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde

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