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

Evgenii I. Rodionov; Alina A. Rodionova; Alla D. Zorina; Olesya V. Khoroshilova; Vitalii V. Suslonov; Elizaveta V. Lider; Yuliya A. Golubeva; Lyubov S. Klyushova; Yuri B. Porozov; Nikolay N. Kuzmich; Rostislav E. Trifonov

doi:10.1016/j.mencom.2024.06.011

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

Evgenii I. Rodionov, Alina A. Rodionova, Alla D. Zorina, Olesya V. Khoroshilova, Vitalii V. Suslonov, Elizaveta V. Lider, Yuliya A. Golubeva, Lyubov S. Klyushova, Yuri B. Porozov, Nikolay N. Kuzmich, Rostislav E. Trifonov^*

^*Corresponding author for this work

Institute of Biochemistry, Food Science and Nutrition

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	505-508
Number of pages	4
Journal	Mendeleev Communications
Volume	34
Issue number	4
DOIs	https://doi.org/10.1016/j.mencom.2024.06.011
State	Published - 1 Jul 2024

Bibliographical note

Publisher Copyright:
© 2024

Keywords

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

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10.1016/j.mencom.2024.06.011

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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. (2024). Synthesis, structure and cytotoxicity of novel tetrazolo[1’,5’-c]-fused 3-aza-A-homosteroids. Mendeleev Communications, 34(4), 505-508. https://doi.org/10.1016/j.mencom.2024.06.011

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title = "Synthesis, structure and cytotoxicity of novel tetrazolo[1{\textquoteright},5{\textquoteright}-c]-fused 3-aza-A-homosteroids",

abstract = "A series of new 1{\textquoteright}H-tetrazolo[1{\textquoteright},5{\textquoteright}-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 = "aza-A-homosteroids, azidation, cytotoxicity, isomerism, M06-2X and MP2 calculations, steroids, tetrazoles, X-ray structures",

author = "Rodionov, {Evgenii I.} and Rodionova, {Alina A.} and Zorina, {Alla D.} and Khoroshilova, {Olesya V.} and Suslonov, {Vitalii V.} and Lider, {Elizaveta V.} and Golubeva, {Yuliya A.} and Klyushova, {Lyubov S.} and Porozov, {Yuri B.} and Kuzmich, {Nikolay N.} and Trifonov, {Rostislav E.}",

note = "Publisher Copyright: {\textcopyright} 2024",

year = "2024",

month = jul,

day = "1",

doi = "10.1016/j.mencom.2024.06.011",

language = "אנגלית",

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AU - Rodionov, Evgenii I.

AU - Rodionova, Alina A.

AU - Zorina, Alla D.

AU - Khoroshilova, Olesya V.

AU - Suslonov, Vitalii V.

AU - Lider, Elizaveta V.

AU - Golubeva, Yuliya A.

AU - Klyushova, Lyubov S.

AU - Porozov, Yuri B.

AU - Kuzmich, Nikolay N.

AU - Trifonov, Rostislav E.

PY - 2024/7/1

Y1 - 2024/7/1

N2 - 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.

AB - 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.

KW - aza-A-homosteroids

KW - azidation

KW - cytotoxicity

KW - isomerism

KW - M06-2X and MP2 calculations

KW - steroids

KW - tetrazoles

KW - X-ray structures

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AN - SCOPUS:85200820882

SN - 0959-9436

VL - 34

SP - 505

EP - 508

JO - Mendeleev Communications

JF - Mendeleev Communications

IS - 4

ER -

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

Abstract

Bibliographical note

Keywords

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