Catalyst-free and multicomponent synthesis of 3-aminoalkylated indoles via a Mannich-type reaction: multitargeted anticancer, tyrosinase and α-glucosidase inhibitory activities

A highly efficient and sustainable approach for the multi-component synthesis of 3-aminoalkylated indoles was investigated via a Mannich-type reaction under catalyst-free conditions, with methanol and ethylene glycol (EG) as the promoting media. Synthesizing various substrates without using column c...

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Bibliographic Details
Published in:New journal of chemistry 2021-10, Vol.45 (38), p.18183-18191
Main Authors: Huynh, Thi-Kim-Chi, Ngo, Kim-Khanh-Huy, Nguyen, Hoang-Phuc, Dang, Hoai-Khanh, Phung, Van-Trung, Thai, Khac-Minh, Hoang, Thi-Kim-Dung
Format: Article
Language:English
Subjects:
Anticancer properties
Binding sites
Cancer
Catalysts
Chemical synthesis
Column chromatography
Ethylene glycol
Glucosidase
Hydrogen bonding
Hydrophobicity
Indoles
Molecular docking
Spectrum analysis
Substrates
Tyrosinase
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Summary:A highly efficient and sustainable approach for the multi-component synthesis of 3-aminoalkylated indoles was investigated via a Mannich-type reaction under catalyst-free conditions, with methanol and ethylene glycol (EG) as the promoting media. Synthesizing various substrates without using column chromatography is time-saving and convenient, which is one of the advantages of this method. In addition, the environmental friendliness is also considered in this research. The synthetic indole derivatives 4a–g and 5a–g, confirmed via spectral analysis, were investigated for their in vitro anticancer activity on human cancer cell lines such as lung (A549), breast (MDA-MB-231) and prostate (PC3) as well as their antityrosinase and α-glucosidase inhibitory activities. Specifically, the results showed that most of the synthesized indoles inhibited both carcinoma and adenocarcinoma cell lines and affected the cytotoxic activity against all three cancer cell lines in the same fashion; moreover, compounds 5e and 5f were shown to be multitargeted anticancer agents. The results of molecular docking studies clarified that the binding of the most potent compounds, 5e and 5f, at the TopI–DNA binding site was through hydrogen bonding as well as hydrophobic interactions and is comparable to camptothecin binding.
ISSN:1144-0546
1369-9261
DOI:10.1039/D1NJ02536H