Laboratory for Redox-active Molecular Systems

Planned project results:

1. We will create a world-class interdisciplinary laboratory that will feature highly-qualified professionals in various fields of studies – organic, elemento-organic chemistry, biochemistry, biology and molecular biology. Uniting professionals in various domains within one structure under the supervision of Prof. Igor Alabugin will significantly improve the efficiency of their cooperation, it will facilitate experience and knowledge exchange and will provide a higher level of conducted research and will allow to significantly improve the productivity and publication activity of the laboratory.
2. An original approach will be created for the synthesis of new types of redox-active molecular systems that will have sterically hindered phenols having a phosphorus-containing functional group in their structure that is responsible for the redox-activirty of generated methylene quinone as well as aza-heterocyclic substituent with terminal primary amino-groups as a pH-sensitive component. The proposed approach is novel and relies on a new reaction of phosphorylated methylene quinones with heterocyclic C-nucleophiles discovered in the group that is new and does not have counterparts in the world. A targeted modification of amino groups of the produced compounds will be performed using aromatic aldehydes and (or) ketones, (tio) isocyanates, chloranhydrides of acids and amino acids as reagents. As a result we will produce a wide range of SHPs that will contain heterocyclic fragments modified with various functional groups - compounds demonstrating high antitumor activity.
3. The laboratory will develop methods of the synthesis of new «hybrid» рН-sensitive phosphorus-containing SHPs that contain a fragment of benzofuroxan as an additional pharmacophoric group. The proposed approach to the synthesis of these compounds is based on nucleophilic substituent of the chlorine atom in nitrochlor benzofuroxans with heteroaromatic and aromatic diamines with the formation of amino benzofuroxans and subsequent interaction of produced intermediate products with phospholated methylene quinones. In the course of this work we will also develop methods of the synthesis of functionalized aminobenzofuroxans based on the interaction of nitroclorbenzofuroxan with diamines and functionalized amines that include tetraalkylammonium and fragments tri(aryl)alkyl phosphonium fragments as well as heterocyclic substituent. We will produce a wide range of new derivatives of aminobenzofuroxan with onium substituents, tertiary amino groups as well as heterocyclic substituents. Our researchers will synthesize novel «hybrid» phosphorus-containing SHPs containing a gragment of nitrobenzofuroxan bound to a fragment of SHP via a (hetero)aromatic «linker».