The synthesis and cytotoxic activity of N -unsubstituted 3-aryl-4-(trifluoromethyl)-4 H -spiro[chromeno[3,4- c ]pyrrolidine-1,11'-indeno[1,2- b ]quinoxalines]

Chemistry of Heterocyclic Compounds(2022)

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Abstract
method for a regio- and stereoselective synthesis of N -unsubstituted 3-aryl-4-(trifluoromethyl)-4 H -spiro[chromeno[3,4- c ]pyrrolidine-1,11'-indeno[1,2- b ]quinoxalines] in 52–85% yields based on the three-component reaction of 3-nitro-2-trifluoromethyl-2 H -chromenes with azomethine ylides generated in situ from benzylamines and indeno[1,2- b ]quinoxalin-11-one by heating under reflux in CH 2 Cl 2 for 2 h in the presence of 0.1 equiv of pyrrolidine was developed. The resulting compounds exhibited moderate cytotoxic activity against HeLa human cervical carcinoma cells in the concentration range of 10 –5 –10 –4 M.
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Key words
azomethine ylides,benzylamines,indeno[1,2-b]quinoxalin-11-one,3-nitro-2-trifluoromethyl-2H-chromenes,spiro[chromeno-[3,4-c]pyrrolidine-1,11'-indeno[1,2-b]quinoxalines],cytotoxic activity,1,3-dipolar cycloaddition,in silico modeling
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