Natural and synthetic coumarins as antileishmanial agents: A review

Gonçalves, Guilherme Arraché; Spillere, Adriano Ronchi; Neves, Gustavo Machado das; Kagami, Luciano Porto; Poser, Gilsane Lino von; Canto, Rômulo Faria Santos; Eifler‐Lima, Vera Lucia

doi:10.1016/j.ejmech.2020.112514

Cited by 67 publications

(28 citation statements)

References 69 publications

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“…A key bicyclic heterocyclic is coumarin (2H-1-benzopyran-2-one) that is a natural secondary metabolite (SM) extracted from fungus, plants, bacteria, chemical synthesis, as well as essential oils, has been examined as one of the prominent structures to develop novel agents with higher specificity and affinity to different molecular targets showing antioxidant, anticancer, antiviral, anti-inflammatory and antileishmania activities [19][20][21][22][23]. Therefore, diverse families of plants like Umbelliferae, Clusiaceae, and Rutaceae have been used to isolate coumarins [19].…”

Section: Introductionmentioning

confidence: 99%

In silico analysis and identification of antiviral coumarin derivatives against 3-chymotrypsin-like main protease of the novel coronavirus SARS-CoV-2

2021

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Coronavirus disease 2019 (COVID-19) is a pandemic viral disease caused by SARS-CoV-2 that generated serious damages for both the human population and the global economy. Therefore, it is currently considered as one of the most important global health problems of human societies and there is an urgent need for potent drugs or vaccines which can effectively combat this virus. The chymotrypsin-like protease (3CLpro) of SARS-CoV-2 plays a key role in the viral replication inside the host and thus is a promising drug target to design and develop effective antiviral drugs against SARS and other coronaviruses. This study evaluated some antiviral coumarin phytochemicals as potential inhibitors of coronaviruses 3CLpro by in silico approaches such as molecular docking, ADMET prediction, molecular dynamics simulation, and MM-PBSA binding energy calculation. Natural coumarin derivatives were docked to the 3CLpro of SARS-CoV-2 and for further investigation, docked to the 3CLpro of SARS-CoV and MERS-CoV. The docking scores of these natural compounds were compared with 3CLpro referenced inhibitors (ritonavir and lopinavir) and co-crystal inhibitor N3. Molecular docking studies suggested more than half of the coumarin phytochemicals had favorable interaction at the binding pocket of the coronaviruses 3CLpro and exhibited better binding affinities toward 3CLpro than ritonavir and lopinavir. Most antiviral phytochemicals interact strongly with one or both the catalytic dyad residues (His41 and Cys145) and the other key residues of SARS-CoV-2 main protease. Further, MD simulation and binding free energy calculations using MM-PBSA were carried out for three 3CLpro-coumarin complexes and 3CLpro-N3/lopinavir. The results confirmed that the 3CLpro-glycycoumarin, 3CLpro-oxypeucedanin hydrate, and 3CLpro-inophyllum P complexes were highly stable, experience fewer conformation fluctuations and share a similar degree of compactness. Also, the pharmacokinetics and drug-likeness studies showed good results for the selected coumarin phytochemicals.Therefore, the coumarin phytochemicals could be used as antiviral agents in the treatment of COVID-19 after further studies.

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Section: Introductionmentioning

confidence: 99%

In silico analysis and identification of antiviral coumarin derivatives against 3-chymotrypsin-like main protease of the novel coronavirus SARS-CoV-2

2021

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“…1,2 Furthermore, coumarins and their derivatives are seen to be the pivotal components of a plethora of many natural products and pharmaceuticals 3 and synthetic dyes. [4][5][6][7][8][9] The pharmacological activities discovered amongst coumarin derivatives include the treatment categories of Alzheimer's 10 and haematopoietic necrosis (IHN); 11 they have shown potent anticoagulant, antibiotic, antiembolic, antioxidative, and anti-ischemic activities [12][13][14][15][16] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

et al. 2021

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“…Coumarins are important naturally occurring plant constituents and display a wide range of pharmacological and biological activities, such as anticancer [ 1 ], antibacterial [ 2 ], and antifungal [ 3 ]. Moreover, coumarin derivatives have shown activity against neglected diseases as leishmaniasis [ 4 ], tuberculosis [ 5 – 6 ] and Chagas’ disease [ 7 ]. Examples of coumarin-derived drugs are: methoxsalen, used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas; warfarin, an anticoagulant, used to treat blood clots such as deep vein thrombosis and pulmonary embolism, and to prevent stroke; and tioclomarol, also an anticoagulant, that is a long-acting vitamin K antagonist ( Figure 1 ) [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric organocatalyzed synthesis of coumarin derivatives

Moreira¹,

Martelli²,

Corrêa³

2021

Beilstein J. Org. Chem.

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Coumarin derivatives are essential scaffolds in medicinal and synthetic chemistry. Compounds of this class have shown important activities, such as anticancer and antiparasitic, besides the commercially available drugs. These properties led to the development of efficient and greener synthetic methods to achieve the 2H-chromen-2-one core. In this context, the advances in asymmetric organocatalyzed synthesis of coumarin derivatives are discussed in this review, according to the mode of activation of the catalyst.

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Natural and synthetic coumarins as antileishmanial agents: A review

Cited by 67 publications

References 69 publications

In silico analysis and identification of antiviral coumarin derivatives against 3-chymotrypsin-like main protease of the novel coronavirus SARS-CoV-2

In silico analysis and identification of antiviral coumarin derivatives against 3-chymotrypsin-like main protease of the novel coronavirus SARS-CoV-2

3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

Asymmetric organocatalyzed synthesis of coumarin derivatives

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