RUDN University Chemists Propose a One-Step Synthesis of Substances for Medicine
Traditional chemical synthesis goes in several stages and requires the isolation and purification of intermediates at each stage. It is not efficient and not environmentally friendly as it increases the loss of substances and the consumption of solvents, and there is a problem of waste disposal. Therefore, modern chemistry is trying to replace multi-stage reactions with multicomponent ones, in which several compounds react to form a product in a single stage. Reactions with isocyanides are the most popular in multicomponent chemistry. Isocyanides are organic compounds with high reactivity. RUDN University chemists have discovered a new three-component reaction with isocyanides that results in a heterocyclic compound with biological activity, acetimidamides. They contain a fragment of indole, which is used for the synthesis of hormones, indomethacin, and other drugs. This work is a development of the famous Ugi reaction.
“Isocyanide-based multicomponent reactions play an outstanding role in the syntheses of heterocycles, biologically relevant compounds and for diversity-oriented synthesis. In the case of the famous Ugi reaction, isocyanide interacts with iminium salt generated in situ. The potency of methods, based on the Ugi reaction, increases with the possibility of subsequent modification or cyclization of obtained products of multicomponent reaction. This is promising from the point of view of medical chemistry”, said Nikita Golantsov, PhD, Professor of the Department of Organic Chemistry of the RUDN University.
Apart from isocyanides, the new three-component reaction involves a 3-arylidenindoleninium salt and an amine. In total chemists used 8 salts and 13 amines. To choose the optimal reaction conditions, they tested 6 types of solvents, alternated the reaction time and temperature. After the reaction was completed, the chemists isolated the final product by treatment with a saturated baking soda solution followed by chromatography and studied its composition and structure using various methods, including nuclear magnetic resonance (NMR) spectroscopy.
In total, the RUDN University chemists obtained 16 acetimidamides. When using isocyanoacetic ester, imidamides were further cyclized with the formation of an imidazolone fragment. Thus, a series of 19 imidazolones containing an indole substituent was synthesized. The most suitable solvent was acetonitrile. It allowed to minimize the formation of by-products. After three hours at a temperature of 20℃, the reaction yield (the ratio of the actual mass of the product obtained to the theoretical one), was 75%. And after 12 hours, the output reached 96%. Chemists tried to accelerate the reaction by increasing the temperature, but this attempt was unsuccessful due to a tar formation and an increase in the amount of the by-product.
“These reactions furnish a new practical synthetic approach to a series of compounds with a privileged indole scaffold, which are prospective choices for seeking new physiologically active compounds”, said Nikita Golantsov, PhD, Professor of the Department of Organic Chemistry of the RUDN University.
RUDN summarized the results of the scientific competition "Project Start: work of the science club ". Students of the Faculty of Physics, Mathematics and Natural Sciences have created a project for a managed queuing system using a neural network to redistribute resources between 5G segments. How to increase flexibility, make the network fast and inexpensive and reach more users — tell Gebrial Ibram Esam Zekri ("Fundamental Computer Science and Information Technology", Master's degree, II course) and Ksenia Leontieva ("Applied Mathematics and Computer Science", Master's degree, I course).
The National Demographic Report, 2023 Demographic Well-Being of Russian Regions (hereinafter - the National Demographic Report) was prepared by the scientific team of the Institute of Demographic Studies of the Federal Research Center of the Russian Academy of Sciences, the Vologda Scientific Center of the Russian Academy of Sciences, Peoples' Friendship University of Russia, the Center for Family and Demography of the Academy of Sciences of the Republic of Tatarstan, as well as with the participation of leading scientists from the Republic of Bashkortostan, Stavropol Krai, Volgograd, Ivanovo, Kaliningrad, Nizhny Novgorod, Sverdlovsk Oblasts and Khanty-Mansi Autonomous Okrug–Yugra.
RUDN summarized the results of the scientific competition "Project Start: work of the science club ". Students of the Faculty of Physics, Mathematics and Natural Sciences have created a project for a managed queuing system using a neural network to redistribute resources between 5G segments. How to increase flexibility, make the network fast and inexpensive and reach more users — tell Gebrial Ibram Esam Zekri ("Fundamental Computer Science and Information Technology", Master's degree, II course) and Ksenia Leontieva ("Applied Mathematics and Computer Science", Master's degree, I course).
What is your first association with the word “laboratory”? Flasks and beakers? Microscopes and centrifuges? Yes, many of us would answer the same way.
The National Demographic Report, 2023 Demographic Well-Being of Russian Regions (hereinafter - the National Demographic Report) was prepared by the scientific team of the Institute of Demographic Studies of the Federal Research Center of the Russian Academy of Sciences, the Vologda Scientific Center of the Russian Academy of Sciences, Peoples' Friendship University of Russia, the Center for Family and Demography of the Academy of Sciences of the Republic of Tatarstan, as well as with the participation of leading scientists from the Republic of Bashkortostan, Stavropol Krai, Volgograd, Ivanovo, Kaliningrad, Nizhny Novgorod, Sverdlovsk Oblasts and Khanty-Mansi Autonomous Okrug–Yugra.