Design, Synthesis, and Biological Evaluation of γ‐Aminopropyl Silatrane–Acyclovir Hybrids with Immunomodulatory Effects

Abstract

Several derivatives of γ-aminopropyl silatrane containing acyclovir in their molecular structure were synthesized and evaluated for their immunomodulatory and antiviral activities. The structures of all these derivatives were confirmed by mass spectra, IR, and (1) H NMR. Based on WST-1 assay in vitro, these compounds could stimulate proliferation of splenic lymphocytes at certain concentrations. Furthermore, compound 3d could also potentiate the expression of IFN-γ, IL-2, CD4(+) , CD8(+) , and CD4(+) /CD8(+) in vivo. Our results show that these derivatives possess antiviral activity against herpes simplex viruses with a similar potency to acyclovir without a cellular immune response.

New atranes and similar ionic complexes. Synthesis, structure, properties

“…Functionalization of silatranes with different groups in exocyclic position is an important trend as the resulting compounds retain the activities of silatranes as well as substituted groups …”

“…3‐Aminopropylsilatrane represents a convenient building block for design of numerous new advanced materials and pharmacologically active compounds . On the other hand, aldehydes are known to react with primary amines to deliver imines which can also be employed as precursors of drugs including antitumor ones …”

“…For example, silatranes. Due to their unusual architecture (the N → Si bond, the pentacoordinated silicon atom, the tricyclic structure), high dipole moment and strong electron‐donating effect of the silatrane skeleton, silatranes are of interest not only as theoretical objects but also as important functional reagents, advanced materials (Si‐organic polyimide films, catalysts, optical probes, adhesion layers for nanoparticles), as well as physiologically and pharmacologically active compounds …”

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

“…In addition, 3‐aminopropylsilatranes and their derivatives show antimicrobial, [ 12,13 ] antiparasitic, [ 14 ] antihepatitis B, [ 15 ] antitumor, [ 16 ] immunomodulatory [ 17 ] and growth stimulating [ 18 ] activity.…”

Mechanism of Reactions of 1-Substituted Silatranes and Germatranes, 2,2-Disubstituted Silocanes and Germocanes, 1,1,1-Trisubstituted Hyposilatranes and Hypogermatranes with Alcohols (Methanol, Ethanol): DFT Study

“…The most studied compounds of the elements of group 14 are silatranes and germatranes, as well as their bicyclic analogues–ocanes and monocyclic–hypoatranes. The diverse biological activity of atrane systems depends on the nature of the substituents, and such compounds can be both effective immunostimulants and adaptogens, and immunosuppressants, thus providing a stimulating or inhibiting effect on the vital activity of micro- and macroorganisms [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. In addition, atranes are used as important functional reagents [ 11 , 12 , 13 , 14 , 15 ], catalysts for the formation of polyurethanes [ 16 , 17 ].…”