Hybrids of imidazole with indoline derivatives: Microwave assisted synthesis, molecular docking studies, possible biological activities

A new hybrids of imidazole with Indole derivative 1-methyl-3-((1-(2-methyl-1H-Imidazole. -1yl)-methyl)-1H-indol-5-yl)imino)indolin-2-one(3a-o) was prepared by microwave-assisted technique via alkylation and Schiff's and Mannich base mechanism. The chemical structures of the synthesized products...

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Bibliographic Details
Published in:Journal of the Indian Chemical Society 2024-04, Vol.101 (4), p.101143, Article 101143
Main Authors: Sultana, Shaheen, P, Pandian, Gupta, Jeetendra Kumar, B, Rajkamal, Barmavatu, Praveen, Mohanty, Dibyalochan
Format: Article
Language:English
Subjects:
Anthelmintic
Anticancer activity
Indole
MCF-7
Molecular docking
SKOV3 cells lines
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Summary:A new hybrids of imidazole with Indole derivative 1-methyl-3-((1-(2-methyl-1H-Imidazole. -1yl)-methyl)-1H-indol-5-yl)imino)indolin-2-one(3a-o) was prepared by microwave-assisted technique via alkylation and Schiff's and Mannich base mechanism. The chemical structures of the synthesized products were confirmed by IR, 1HNMR and Mass spectra. The in vitro anticancer activity was evaluated via MTT assay technique, as well as their anthelmintic activity by utilising Indian earth warms. Most of the compounds 1-methyl-3-((1-(2-methyl-1H-Imidazole-1yl)-methyl)-1H-indol-5-yl)imino)indolin-2-one demonstrated greater anthelmintic action than the other compounds. The compounds 1,5-dimethyl-3-((1-(2-methyl-1H-Imidazole-1-yl)-methyl)-1H-indol-5-yl)-imino)-indole-2-one and 1-benzyl-5--chloro-3-((1-((2-methyl-1H--imidazole-1-yl) methyl)-1H-indol-5-yl) imino)indolin-2-one exhibit good anticancer action. Lastly, whenever the interaction pattern and selectivity towards the EGFR activity site have been examined, the molecular docking experiments of novel indole derivatives demonstrated good alignment only with biological findings. •Novel indole derivatives were synthesized by microwave assisted synthesis.•All the structures were confirmed by IR, 1HNMR and Mass spectral analysis.•Their in-vitro anticancer activity was evaluated via MTT assay technique.•The compounds 3c and 3m exhibit good anticancer action.•Amongst docked ligands, molecule 3b had the good dock value of −5.595 and binding energy of −37.004 kcal/mol.
ISSN:0019-4522
DOI:10.1016/j.jics.2024.101143