Synthesis and biological evaluation of -alkyl naphthoimidazoles derived from β-lapachone against bloodstream trypomastigotes.

The QSAR study of 34 2-aryl-naphthoimidazoles screened so far revealed that is the most important factor for their lytic activity on the bloodstream trypomastigote forms of , the etiologic agent of Chagas disease. Based on this result, 16 new -alkyl-naphthoimidazoles derived from 6,6-dimethyl-3,4,5,6-tetrahydrobenzo[7,8]chromene[5,6-]imidazole (the product of the reaction of β-lapachone with paraformaldehyde) by its reaction with halo-alkanes were prepared and evaluated against the parasite and peritoneal macrophages. The 1--hexyl and 3--hexyl naphthoimidazoles were 2.

3,3-Dimethyl-cis-9a,13a-diphenyl-2,3,9a,11,12,13a-hexa-hydro-1H-benzo[h][1,4]dioxino[2',3':5,6][1,4]dioxino[2,3-f]chromene.

In the title di-hydro-dioxin, C31H28O5, the dioxane ring has a chair conformation, whereas each of the pyran and dioxine rings has an envelope conformation with methyl-ene and quaternary C atoms, respectively, being the flap atoms. The phenyl rings are cis and form a dihedral angle of 82.11 (10)°.