In vitro studies of a series of synthetic compounds for their anti-acetylcholinesterase activities identified arylpyrano[2,3-f]coumarins as hit compounds

Martin, Erlon F.; Pollo, Luiz A.E.; Silva, Layzon Antonio Lemos da; Biavatti, Maique W.; Sandjo, Louis P.

doi:10.1016/j.molstruc.2022.132799

Cited by 3 publications

(3 citation statements)

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“…Twenty‐one chalcone derivatives ( 1 – 14 , 15a , 15b , 16 – 20 ) from our laboratory were previously obtained from two aromatic ketones namely 3,5‐difluoroacetophenone and 3‐acetyl‐ N ‐methylpyrrole treated with different aldehydes ( Scheme 1). [12] This series prepared by Claisen‐Schmidt condensation was considered a pilot to identify the suitable skeleton with promising inhibitory effects against SARS‐CoV‐2 M pro . Compound 10 succeeded in impairing this enzyme activity with a percentage greater than 50 %.…”

Section: Resultsmentioning

confidence: 99%

“…Preparation and characterization of compounds 1 – 20 were previously reported in the literature [12] …”

Section: Methodsmentioning

confidence: 99%

“…Preparation and characterization of compounds 1 -20 were previously reported in the literature. [12] General Procedure for the Indole C3-Formylation To a solution of indole (1.0 mmol), hexamethylenetetramine (HMTA) (2.0 mmol), activated carbon (0.1 g), and DMF (2 mL). Then I 2 (20 mol%) was added and the flask was equipped with a reflux condenser.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

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Studies of Cytotoxicity Effects, SARS‐CoV‐2 Main Protease Inhibition, and in Silico Interactions of Synthetic Chalcones

Fernandes

Tizziani

Dambrós

et al. 2023

Chemistry & Biodiversity

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SARS-CoV-2 main protease (M pro ) plays an essential role in proteolysis cleavage that promotes coronavirus replication. Thus, attenuating the activity of this enzyme represents a strategy to develop antiviral agents. We report inhibitory effects against M pro of 40 synthetic chalcones, and cytotoxicity activities, hemolysis, and in silico interactions of active compounds. Seven of them bearing a (E)-3-(furan-2-yl)-1-arylprop-2-en-1-one skeleton (10, 28, and 35-39) showed enzyme inhibition with IC 50 ranging from 13.76 and 36.13 μM. Except for 35 and 36, other active compounds were not cytotoxic up to 150 μM against THP-1 and Vero cell lines. Compounds 10, and 35-39 showed no hemolysis while 28 was weakly hemotoxic at 150 μM. Moreover, molecular docking showed interactions between compound 10 and M pro (PDBID 5RG2 and 5RG3) with proximity to cys145 and His41, suggesting a covalent binding. Products of the reaction between chalcones and cyclohexanethiol indicated that this binding could be a Michael addition type.

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Section: Resultsmentioning

confidence: 99%

“…Preparation and characterization of compounds 1 – 20 were previously reported in the literature [12] …”

Section: Methodsmentioning

confidence: 99%

Section: Synthetic Proceduresmentioning

confidence: 99%

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