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

Evgenii I Rodionov 1
Evgenii I Rodionov
, 
Alina A Rodionova 1
Alina A Rodionova
, 
Alla Dmitrievna Zorina 2
Alla Dmitrievna Zorina
, 
Olesya V Khoroshilova 2
Olesya V Khoroshilova
, 
Vitalii Valeryevich Suslonov 2, 3, 4
Vitalii Valeryevich Suslonov
, 
Elizaveta Victorovna Lider 5
Elizaveta Victorovna Lider
, 
Yuliya Andreevna Golubeva 5
Yuliya Andreevna Golubeva
, 
Lyubov Sergeevna Klyushova 6
Lyubov Sergeevna Klyushova
, 
Yuri Borisovich Porozov 7, 8
Yuri Borisovich Porozov
, 
Nikolay N Kuzmich 9
Nikolay N Kuzmich
, 
Rostislav Evgen'evich Trifonov 1
Rostislav Evgen'evich Trifonov
1 St. Petersburg State Institute of Technology (Technical University), St. Petersburg, Russian Federation
2 Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
3 S.M. Kirov Military Medical Academy, St. Petersburg, Russian Federation
4 National Research Tomsk Polytechnic University, Tomsk, Russian Federation
5 A.V. Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
6 Institute of Molecular Biology and Biophysics, Federal Research Center of Fundamental and Translational Medicine, Novosibirsk, Russian Federation
7 Advitam Laboratory, Belgrade, Serbia
8 St. Peterburg School of Physics, Mathematics, and Computer Science, HSE University, St. Peterburg, Russian FEderation
9 Weizmann Institute of Science, Rehovot, Israel
10.1016/j.mencom.2024.06.011
Published 2024-06-19
Communication , Volume 34, Issue 4, 505-508
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Rodionov E. I. et al. Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 505-508.
GOST all authors (up to 50) Copy
Rodionov E. I., Rodionova A. A., Zorina A. D., Khoroshilova O. V., Suslonov V. V., Lider E. V., Golubeva Y. A., Klyushova L. S., Porozov Y. B., Kuzmich N. N., Trifonov R. E. Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 505-508.
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TY - JOUR
DO - 10.1016/j.mencom.2024.06.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.011
TI - Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids
T2 - Mendeleev Communications
AU - Rodionov, Evgenii I
AU - Rodionova, Alina A
AU - Zorina, Alla Dmitrievna
AU - Khoroshilova, Olesya V
AU - Suslonov, Vitalii Valeryevich
AU - Lider, Elizaveta Victorovna
AU - Golubeva, Yuliya Andreevna
AU - Klyushova, Lyubov Sergeevna
AU - Porozov, Yuri Borisovich
AU - Kuzmich, Nikolay N
AU - Trifonov, Rostislav Evgen'evich
PY - 2024
DA - 2024/06/19
PB - Mendeleev Communications
SP - 505-508
IS - 4
VL - 34
ER -
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@article{2024_Rodionov,
author = {Evgenii I Rodionov and Alina A Rodionova and Alla Dmitrievna Zorina and Olesya V Khoroshilova and Vitalii Valeryevich Suslonov and Elizaveta Victorovna Lider and Yuliya Andreevna Golubeva and Lyubov Sergeevna Klyushova and Yuri Borisovich Porozov and Nikolay N Kuzmich and Rostislav Evgen'evich Trifonov},
title = {Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.011},
number = {4},
pages = {505--508},
doi = {10.1016/j.mencom.2024.06.011}
}
MLA
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MLA Copy
Rodionov, Evgenii I., et al. “Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids.” Mendeleev Communications, vol. 34, no. 4, Jun. 2024, pp. 505-508. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.011.

Keywords

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

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.

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