Synthesis, Crystal Structure, Solution Study and In Silico ADME Profiling of Various Asymmetric Functionalized Triazenes

Abstract

Syntheses of some ligands based on asymmetric triazenes consisting 1-(2-methoxycarbonylphenyl)-3-(2-methylphenyl)triazene (1), 1-(2-methoxycarbonylphenyl)-3-(3-methylphenyl)triazene (2), 1-(2-methoxycarbonylphenyl)-3-(4-methylphenyl)triazene (3), 1-(2-methoxycarbonylphenyl)-3-(3,5-dichlorophenyl)triazene (4), 1-(4-chlorophenyl)-3-(4-methylphenyl)-triazene (5) and their related Hg II complexes were reported. The characterizations were performed by FT-IR, 1 H NMR and 13 C NMR spectroscopies. In (3) and (4), both triazenes possess trans-conformation around the (-N=N-) bond and monomeric moieties are linked to pairs and wave-like chains through C-HÁÁÁO and C-HÁÁÁN hydrogen bonds which are further assembled by stacking through secondary pÁÁÁp interactions [3.829(1) and 3.736(1) Å ]. The reaction of (1) and Hg(NO 3 ) 2 in methanol produces the corresponding Hg II complex (6) where each triazenide binds to the Hg II atom through two nitrogen atoms of triazenide and one oxygen atom of pendant methoxycarbonyl group forming distorted MN 4 O 2 octahedral around the Hg II atom. The stoichiometry and formation of complex (6) and (8) in methanol solution were investigated by UV-Vis titration. Moreover, Reaction of substituted 1,3-diaryltriazenes (2) and (5) with Hg II salts afford a family of orange complexes (7) and (8), respectively. Finally, the chemical structures of the investigated ligands were correlated to their pharmacokinetic behaviour using five pre-calculated models implemented in VolSurf program. Graphical Abstract Polyhedron around HgII atom coordinated by two triazenide ligands in an octahedron fashion.