Synthesis, structural characterization and biological activity of helicin thiosemicarbazone monohydrate and a copper(II) complex of salicylaldehyde thiosemicarbazone

摘要

Two new compounds, helicin (i.e. salicylaldehyde-#beta#-D-glycoside) thiosemicarbazone monohydrate, Het centre dot H_2O (1), and bis[aqua(salicylaldehyde thiosemicarbazonato)copper(II)]sulfate bisdimethylsulfoxide solvate hexahydrate [Cu(Hsalt)(OH_2)]_2SO_4 centre dot 2DMSO centre dot 6H_2O (2) (H_2salt = salicylaldehyde thiosemicarbazone) were synthesized and characterized by means of NMR, IR and X-ray techniques. Molecule 1 consists of three units: the sugar, the benzene ring and the thiosemicarbazonic chain. In the reaction of 1 with CuSO_4 the helicin thiosemicarbazone was hydrolyzed giving rise to the salicylaldehyde thiosemicarbazone, so forming complex 2. The molecular structure of 2 consists of centrosymmetric dimeric cations, sulfate anions lying on a crystallographic two-fold axis, DMSO and water solvate molecules. The dimeric cations are due to a long Cu-aromatic ring interaction. Moreover, for both compounds assays of proliferation inhibition and apoptosis tests in vitro on human leukemic cell lines U937 were carried out.