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Under catalyst-free conditions, an environmentally friendly synthesis of a class of spiropyrane, spiropyranopyrazole, spirobenzofurane, spirobenzofuropyrazole, spirooxadiazolidine, spiro-triazolooxadiazole, spirotriazole, and spirophenanthrene from isatin and different reagents was designed, synthesized, and evaluated for their anticancer activities. Compounds  3 ,  4 , and  9  were formed via a one-pot three-component fusion, and the process of synthesis was interpreted using Knoevenagel condensation, Michael addition, and intramolecular cyclization. The technique of preparation has important benefits such as simple reaction conditions, an easy work-up method, simple separation, and nonchromatographic purification of the products. The  1 H,  13 C-NMR, and mass spectra of the investigated compounds ( 2 – 10 ) were estimated and matched rather well with the experimental results. The National Cancer Institute (NCI, Bethesda, USA) examined all produced derivatives and found that compound  3  had high anti-cancer cell line activity against non-small cell lung-HCI-H522 (GI% = 93.52%) and melanoma-LOX IMVI (GI%=71.63%). Compounds  7  and  8  also showed inhibitory action, with mean GI% ranging from 9.63% to 35.90%. While Compound  10  demonstrated efficacy against a variety of cell lines representing multiple tumor subpanels, with GI% equal to or more than 40%. Docking experiments with Tyrosine Kinase (PDB ID:  2J5F ) were carried out to validate NCI findings. In silico investigations revealed that the majority of the produced spiro compounds satisfied Lipinski’s criteria.

Novel Indoline Spiro Derivatives As Anticancer Agents; Design, Synthesis, Molecular Docking Studies, and ADME Evaluation