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This new investigation describes an efficient three-component approach for the stereoselective synthesis of pyrrolo[2,1-a]isoquinolines from readily available isatins, chalcones and 1,2,3,4-tetrahydroisoquinoline without using a metal catalyst or additive. The synthetic methodology was found to be equally successful with differently functionalised secondary amines. A series of pyrrolo[2,1-a]isoquinolines were synthesised in good yields (up to 87%), and a single diastereomer product was formed exclusively in all the cases. The comprehensive analysis of the interaction between the ligand and the receptor obtained from in silico molecular docking on the active sites of ACP reductase (4OHU) indicates that our synthesised compounds have better anti-tuberculosis properties than the standard drug Rifampicin.