Indolyl-4H-chromenes: Multicomponent one-pot green synthesis, in vitro and in silico, anticancer and antioxidant studies

The present work describes the simple, economical and eco-friendly multicomponent one-pot synthesis of indolyl-4 H -chromene derivatives. It is being achieved by reacting benzaldehydes, nitroketene N,S acetals and indoles in the presence of 1,4-diazabicyclo[2.2.2]octane as catalyst and ethanol, a green solvent. In this domino transformation, a new 4 H -chromene, a six-membered heterocyclic ring has been generated by the concurrent formation of two C -C and one C -O bond. The rampant spread of cancer and disorders associated with cancers necessitated us to evaluate the dual active potentials of these new indolyl-4 H -chromenes derivatives as anticancer and anti-oxidant agents. In silico assay of C2- N -phenyl substituted indolyl-4 H -chromene against laryngeal (1sa0), breast (5nwh), and cervical carcinoma (4 giz) proteins. From DFT studies, we have analyzed the R and S isomers of compound 4a-l and also the MO of all the compounds analyzed. The in vitro and in silico results taken together indicate that the compound 4e is the promising dual active lead with IC 50 values at 0.75 +/- 0.06 mu M, 0.75 +/- 0.04 mu M and 10 +/- 0.91 mu M concentrations against Hep2, A549 and HeLa, respectively and 84.96% anti-oxidant activity. (c) 2022 Elsevier B.V. All rights reserved.