Synthèse, caractérisation et propriétés multiples de nouveaux composés à base de Dapsone.

Abstract

The 4,4'-diamino diphenyl sulfone, better known as Dapsone (DDS) is the simplest sulfone. Synthesized for over a century and better known for its antibacterial and anti-inflammatory activity. The work presented in this thesis has for aim the synthesis, the characterization and the structural study of new compounds having for matrix the molecule of DDS, as well as the evaluation of their biological activities and the investigation of their magnetic, luminescent and non-linear optical properties. During our research we were able to synthesize nine new compounds:  Six new complexes with the DDS ligand, four based on Cu (II): one monomeric complex the aqua-bis(4,4’- diaminodiphenylsulfone- κN,N’)-(dinitrato-κO) copper (II), an organic-inorganic hybrid compound Diaquabis(4,4’-diaminodiphenylsulfone-κN,N’)-bis(N,N’-dimethylformamide- kO) copper (II) dinitrate, an ionic cocrystal Bis(2.2'-bipyridyl-κ2N,N’)-(nitrato-k2O,O’) copper (II) Nitrate bis(4,4’-diaminodiphenylsulfone) Trihydrate, a two-dimensional cadmium (II) coordination polymer catena-[(2,-4,4'-sulfonyldianiline k2N:N’)-aqua- (µ2-nitrato-k2O:O’) (di nitrato-k2O,O’) cadmium], a copper 1D-MOF’s catena-poly[cyclo-bis (µ2-4,4'- diaminodiphenylsulfone- k2N,N’)-diaqua (µ2-chlorido) -(trichloro) dicopper(II)] monohydrate, the last compound is a p-nitroaniline cadmium coordination complexe diaqua-bis(4-nitroaniline κN)-(dinitrato-κO) cadmium (II). The coordination complexes were characterized by IR spectroscopy and X-ray diffraction on powder and single crystal, their structural study was reinforced by an additional study, namely the Hirshfeld surface analysis. The magnetic properties of complexes (I), (II) and (III) have been studied both (I) and (II) have paramagnetic properties while (III) shows week antiferromagnetic coupling. The luminescent properties of the complex (IV) were investigated in solid and liquid state with a strong emission in the green region. The biological properties of complexes (I), (II) and (IV) as well as those of the DDS molecule were assessed, the results obtained shows a clear improvement of the antibacterial activity of the synthesized complexes in comparison with those of the parent molecule. Antioxydant activities of compounds (I), (II), (III) and (IV) was investigated neither of the compounds is a good antioxydant inhibitor. Enzymatic UREASE activity of compound (I) and (VI) were assessed. IC50 of compound (VI) proved better inhibitor activity than Thiourea. Even thought IC50 of compound (I) couldn’t be measured, the compound showed promising inhibitory activity.  Three new hybrid compounds, namely (4-amino, 4ʹ-azaniumyldiphenyl) sulfone nitrate, (4,4ʹ- diazaniumyldiphenyl) sulfone dinitrate and Bis [di (4-azaniumylphenyl) sulfone tetranitrate monohydrate were characterized by IR spectroscopy, and X-ray diffraction on single crystal were obtained, their nonlinear optical properties were evaluated, compound (I) and (II) showed good properties respectively of 2 and 1.23 times those of KDP, while (III) showed no NLO property. Antibacterial activities of compounds (I) and (II) showed comparable results to that of DDS molecule, and in contrario to the DDS molecule hybrid compound was water-soluble.