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Development of Biostimulants and Pharmaceuticals Using Synthetic Heavy-Heteroatom Organic Compounds

: Organic compounds containing heteroatoms in the third row of the periodic table, particularly sulfur and phosphorous, are widely used in pharmaceuticals and biostimulants. It is essential to develop novel efficient synthetic methods for heavy-heteroatom organic compounds containing sulfur and phosphorous atoms. Compared with oxygen and nitrogen atoms, which are second-row heteroatoms, sulfur and phosphorous atoms are larger, polarizable, and oxidizable. Thus, these heavy-heteroatom organic compounds can interact well with biomacromolecules and exhibit diverse biological functions. In this work, a novel method of synthesizing heavy-heteroatom organic compounds using transition-metal catalysts was developed. The reactions use inexpensive sulfur reagents and are reversible and energy-saving without the need to use bases. This transition-metal-catalyst method can be carried out in a homogeneous system in water, and provides chemically modified peptides and proteins. Synthetic compounds for biostimulants and pharmaceuticals have been developed using designed unsymmetric bis(heteroaryl) HetAr–X–HetAr' compounds, which have flexible and rigid HetAr groups containing sulfur and phosphorus atoms capable of interacting with biomacromolecules, and exhibit various biological activities.