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

Two new compounds, helicin (i.e. salicylaldehyde-P-D-glycoside) thiosemicar bazone monohydrate, Het . H2O (1), and bis[aqua(salicylaldehyde thiosemicar bazonato)copper(II)]sulfate bisdimethylsulfoxide solvate hexahydrate [Cu(Hs alt)(OH2)](2)SO4. 2DMSO . 6H(2)O (2) (H(2)salt = salicylaldehyde thiosemica rbazone) were synthesized and characterized by means of NMR, IR and X-ray t echniques. Molecule 1 consists of three units: the sugar, the benzene ring and the thiosemicarbazonic chain. In the reaction of 1 with CuSO4 the helic in thiosemicarbazone was hydrolyzed giving rise to the salicylaldehyde thio semicarbazone, so forming complex 2. The molecular structure of 2 consists of centrosymmetric dimeric cations, sulfate anions lying on a crystallograp hic two-fold axis, DMSO and water solvate molecules. The dimeric cations ar e due to a long Cu-aromatic ring interaction. Moreover, for both compounds assays of proliferation inhibition and apoptosis tests in vitro on human le ukemic cell lines U937 were carried out. (C) 1999 Elsevier Science S.A. All rights reserved.