Scientists Develop Method to Improve Known Drugs and Create New Ones

Chemists from St. Petersburg State University have developed a method for producing new organic substances based on a simple reaction triggered by organic sulfur compounds. The resulting substances have a structure similar to drugs with anti-inflammatory, antibacterial, and antitumor activity, which could form the basis for new medicinal compounds.

The thiol-ene reaction — a chemical process in which two carbon fragments are linked through a sulfur atom — is widely used in medicine and materials chemistry to create polymer networks or modify nanoparticles. This method is also promising for creating new small sulfur-containing molecules. This specifically refers to aminoketones — substances that contain both amino and carbonyl groups and can be used in drug development. However, to achieve this, both the reagents and the reaction conditions must be chosen very carefully.

Researchers from St. Petersburg State University have synthesized sulfur-containing aminoketones for the first time by combining nitrogen compounds with thiol reagents. They tested various combinations of additives and solvents and found an optimal solution using potassium carbonate: due to its poor solubility in organic matter, it is easily removed from the reaction mixture upon completion of the process. This can be done through simple filtration, which significantly simplifies the purification of the final product.

Thus, the authors found not only an effective but also a technologically efficient method for conducting the synthesis. At room temperature, the scientists obtained 16 products with a substance yield of up to 95%. Using the developed approach, the St. Petersburg State University chemists modified known anti-inflammatory and antibacterial drugs, transforming them into new aminoketone structures.

By using more complex precursors, they discovered that the resulting hybrid molecules spontaneously cyclize, forming aziridines (three-membered nitrogen-containing cycles). The scientists obtained 15 such heterocycles, whose structural fragment matches that of natural anticancer agents. This opens up prospects for the development of new antitumor drugs.

"For the first time, we have managed to obtain unique aminoketones and aziridine systems using a reaction that is simple, fast, and requires no heating. This work will give impetus to the development of classical thiol-ene chemistry. The data obtained will help in the creation of new drugs to combat inflammation and cancer," said the project leader, Head of the Department of Organic Chemistry at St. Petersburg State University, Nikolai Rostovsky.

In the future, the scientists plan to continue the synthesis of socially significant substances based on available organic precursors.

More information:
Nazar A. Moshnenko et al, Thiol–Ene Reaction of 1-Azabuta-1,3-dienes in Synthesis of Functionalized α-Amino Ketones and Fused Aziridines, Organic Letters (2026). DOI: 10.1021/acs.orglett.6c00096

Provided by St. Petersburg State University