E. I. Rodionov, A. A. Rodionova, A. D. Zorina, O. V. Khoroshilova, V. V. Suslonov, E. V. Lider, Yu. A. Golubeva, L. S. Klyushova, Yu. B. Porozov, N. N. Kuzmich, R. E. Trifonov, “Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids”, Mendeleev Commun., 2024, Volume 34, Issue 4,Pages 505

Communications

Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids

E. I. Rodionov^a, A. A. Rodionova^a, A. D. Zorina^b, O. V. Khoroshilova^b, V. V. Suslonov^bcd, E. V. Lider^e, Yu. A. Golubeva^e, L. S. Klyushova^f, Yu. B. Porozov^gh, N. N. Kuzmichⁱ, R. E. Trifonov^a

^a St. Petersburg State Institute of Technology (Technical University), St. Petersburg, Russian Federation
^b Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
^c S.M. Kirov Military Medical Academy, St. Petersburg, Russian Federation
^d National Research Tomsk Polytechnic University, Tomsk, Russian Federation
^e A.V. Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
^f Institute of Molecular Biology and Biophysics, Federal Research Center of Fundamental and Translational Medicine, Novosibirsk, Russian Federation
^g Advitam Laboratory, Belgrade, Serbia
^h St. Peterburg School of Physics, Mathematics, and Computer Science, HSE University, St. Peterburg, Russian FEderation
ⁱ Weizmann Institute of Science, Rehovot, Israel

Abstract: A series of new 1’H-tetrazolo[1’,5’-c]-fused 3-aza-A- homosteroids were synthesized by azidation of progesterone, testosterone and hydrocortisone acetate in the presence of silicon tetrachloride. According to NMR spectroscopy and X-ray analysis, two double bond positional isomers (double bond in ring A or in ring B) are formed in various ratios; according to quantum chemical calculations, their energies are close within 0.4 kcal mol^-1. Only low cytotoxic activity against Hep-2, MCF-7, HepG2, and Hek293 cell lines was determined in vitro for the compounds obtained.

Keywords: azidation, tetrazoles, steroids, aza-A-homosteroids, isomerism, X-ray structures, M06-2X and MP2 calculations, cytotoxicity.

Language: English

DOI: 10.1016/j.mencom.2024.06.011

	*Supplementary materials:*
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