Synthesis, spectroscopic, in vitro cytotoxicity and crystal structures of novel fluorinated dispiroheterocycles: DFT approach

Abstract

The reaction of azomethine ylide generated in situ from ninhydrin and sarcosine/thiaproline with fluorinated cyclopent[b]indole dipolarophiles in refluxing dioxane and methanol afforded a novel class of fluorinated cyclopent[b]indole dispiroheterocycles via 1,3-dipolar cycloaddition. The crystal structures of 4'-[4-(trifluoromethyl)phenyl]-1',5-dimethyl-2,3-dihydrodispiro[cyclopent[b]-indol-2,3'-pyrrolidine-2',2aEuro(3)-indene]-1,1aEuro(3),3aEuro(3)-trione and 4'-(4-fluorophenyl)-5-methyl-2,3-dihydrodispiro[cyclopent[b]indol-2,3'-pyrrolizidine-2',2aEuro(3)-indene]-1,1aEuro(3),3aEuro(3)-trione are reported. New compounds are investigated theoretically via DFT calculations utilizing M062X hybrid function with 6-311++G(d,p) basis sets in vacuum. Results from in vitro cytotoxicity screening are compared with those of standard drugs. [GRAPHICS]