Coumarin-based derivatives with potential anti-HIV activity

Xu, Zhi; Chen, Qingtai; Zhang, Yan; Liang, Changli

doi:10.1016/j.fitote.2021.104863

Cited by 84 publications

(64 citation statements)

References 95 publications

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“…[ 3 ] As such, coumarins have been intensively studied in recent decades and numerous classes of these compounds have been synthesized and biologically explored, yielding a range of activities such as anti‐inflammatory, anticoagulant, antibacterial, antifungal, antiviral, and anticancer. [ 4–10 ] Apart from being important medicinal leads, coumarins have been widely investigated as fluorescence probes as well. [ 11–14 ]…”

Section: Introductionmentioning

confidence: 99%

Fragment‐type 4‐azolylcoumarin derivatives with anticancer properties

Simić

Petković

Jovanović

et al. 2021

Archiv der Pharmazie

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Several coumarin derivatives with a directly attached azole substituent at C‐4 were synthesized and biologically studied for their anticancer properties. The cell lines used for this investigation (HeLa, K‐562, MDA‐MB‐53, and MCF‐7) demonstrated different sensitivities. The best response in the MTT (3‐(4,5‐dimethyl‐2‐thiazolyl)‐2,5‐diphenyl‐2H‐tetrazolium bromide) assay was shown by K‐562 cells, with compounds displaying activity (3c, IC50 3.06 μM; 4a, IC50 5.24 μM; 4c, IC50 4.7 μM) similar to that of cisplatin (IC50 ~6 μM), which was used as the standard. The studied azole‐substituted coumarins demonstrated weaker activity toward other cell lines, except for compound 4c, which was equally potent in the case of MCF‐7 cells. Additional biological evaluations supported interference with the cell cycle as a potential mechanism of action and confirmed the absence of toxicity in zebrafish embryos. On the basis of these initial results, 4‐azole coumarins should be explored further. Although their activity would need additional optimization, the fact that these compounds are fragment‐like structures with MW <300 and clog P <3 offers enough flexibility to fine‐tune their drug‐like properties.

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Section: Introductionmentioning

confidence: 99%

Fragment‐type 4‐azolylcoumarin derivatives with anticancer properties

Simić

Petković

Jovanović

et al. 2021

Archiv der Pharmazie

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“…Lou, Hou and co-workers also used the same catalyst to perform a regioselective scandium-catalyzed alkylation of 2-phenyl-quinoline derivatives (Scheme 3B) [38]. It is important to highlight the biological importance of quinoline derivatives, since several quinolines are known to present valuable biological activities, such as anti-HIV (5) [48], antiviral in general (6) [49], antituberculotic (7), and antimalarial (8) [50] (Scheme 3A). Using 2-phenylquinoline derivatives as substrates includes some intrinsic challenges, since there are two sites in the molecule where the C-H activation can take place.…”

Section: Review Scandium-catalyzed C-h Activationmentioning

confidence: 99%

“…The discovery of new biologically active substances represents not only an advance in the chemistry field but also offers innovative chances for pharmacological and biomedical sciences. Every year, several molecules are discovered and studied against different types of diseases, such as cancer [1,2], malaria [3,4], Chagas disease [5,6], HIV [7,8], depression [9,10], amnesia [11], Alzheimer [12], and maybe even in a more recent scenario, COVID-19 [13]. Even though many compounds are found to present activity against these diseases, only a few of them become approved, due to their toxicity or other issues Scheme 1: Schematic overview of transition metals studied in C-H activation processes.…”

Section: Introductionmentioning

confidence: 99%

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

Carvalho¹,

Miranda²,

Nunes³

et al. 2021

Beilstein J. Org. Chem.

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Several valuable biologically active molecules can be obtained through C–H activation processes. However, the use of expensive and not readily accessible catalysts complicates the process of pharmacological application of these compounds. A plausible way to overcome this issue is developing and using cheaper, more accessible, and equally effective catalysts. First-row transition (3d) metals have shown to be important catalysts in this matter. This review summarizes the use of 3d metal catalysts in C–H activation processes to obtain potentially (or proved) biologically active compounds.

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“…In recent years, increasing attention has been paid to the role of coumarins as antiviral molecules. Coumarin derivatives could inhibit different stages in the HIV replication cycle, inclusive of virus–host cell attachment; cell membrane fusion; integration; and assembly apart from the conventional target such as inhibition of the reverse transcriptase, protease, and integrase ( Xu et al, 2021 ). In human hepatocytes infected with hepatitis B virus, dicumarol could reduce intracellular HBV RNA, supernatant HBV antigen, and covalently closed circular DNA levels ( Takeuchi et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

Coumarin Derivative N6 as a Novel anti-hantavirus Infection Agent Targeting AKT

Wang

Liu

et al. 2021

Front. Pharmacol.

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Hantaviruses are globally emerging zoonotic viruses that can cause hemorrhagic fever with renal syndrome (HFRS) in Asia and Europe, which is primarily caused by Hantaan virus (HTNV) infection, results in profound morbidity and mortality. However, no specific treatment is available for this disease. Coumarin derivatives have been reported as antiviral molecules, while studies about the bioactivity of coumarin derivatives against HTNV infection are limited. To study the potential antiviral activity of coumarin derivatives, 126 coumarin derivatives are synthesized, and their inhibitory activity against HTNV is analyzed in vitro. Among these compounds, N6 inhibits HTNV with relatively high selectivity index at 10.9, and the viral titer of HTNV is reduced significantly after 5, 10, and 20 μM N6 treatments. Furthermore, the administration of N6 at the early stage of HTNV infection can inhibit the replication and production of infectious HTNV in host cell, this therapeutic efficacy is confirmed in HTNV-infected newborn mice at the early stage of infection. The molecular docking results show that N6 forms interactions with the key amino acid residues at its active site, and reveals several molecular interactions responsible for the observed affinity, and the treatment of N6 can inhibit the expression of p (Ser473)Akt and HTNV nucleocapsid protein significantly. As such, these observations demonstrate that coumarin derivative N6 might be used as a potential agent against HTNV infection.

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Coumarin-based derivatives with potential anti-HIV activity

Cited by 84 publications

References 95 publications

Fragment‐type 4‐azolylcoumarin derivatives with anticancer properties

Fragment‐type 4‐azolylcoumarin derivatives with anticancer properties

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

Coumarin Derivative N6 as a Novel anti-hantavirus Infection Agent Targeting AKT

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