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Synthesis of novel cytotoxic 3-azolylsteroids via Cu-catalyzed C–N coupling

Mikhail Jonovich Parulava 1
Mikhail Jonovich Parulava
, 
Yuri Nikolaevich Kotovshchikov 1
Yuri Nikolaevich Kotovshchikov
, 
Gennadij Vladimirovich Latyshev 1
Gennadij Vladimirovich Latyshev
, 
Darina Vadimovna Sokolova 2, 3
Darina Vadimovna Sokolova
,  , 
Nikolai Vadimovich Lukashev 1
Nikolai Vadimovich Lukashev
10.1016/j.mencom.2021.04.025
Published 2021-04-28
Communication , Volume 31, Issue 3, 359-361
3
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Parulava M. J. et al. Synthesis of novel cytotoxic 3-azolylsteroids via Cu-catalyzed C–N coupling // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 359-361.
GOST all authors (up to 50) Copy
Parulava M. J., Kotovshchikov Y. N., Latyshev G. V., Sokolova D. V., Beletskaya I. P., Lukashev N. V. Synthesis of novel cytotoxic 3-azolylsteroids via Cu-catalyzed C–N coupling // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 359-361.
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TY - JOUR
DO - 10.1016/j.mencom.2021.04.025
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.025
TI - Synthesis of novel cytotoxic 3-azolylsteroids via Cu-catalyzed C–N coupling
T2 - Mendeleev Communications
AU - Parulava, Mikhail Jonovich
AU - Kotovshchikov, Yuri Nikolaevich
AU - Latyshev, Gennadij Vladimirovich
AU - Sokolova, Darina Vadimovna
AU - Beletskaya, Irina Petrovna
AU - Lukashev, Nikolai Vadimovich
PY - 2021
DA - 2021/04/28
PB - Mendeleev Communications
SP - 359-361
IS - 3
VL - 31
ER -
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@article{2021_Parulava,
author = {Mikhail Jonovich Parulava and Yuri Nikolaevich Kotovshchikov and Gennadij Vladimirovich Latyshev and Darina Vadimovna Sokolova and Irina Petrovna Beletskaya and Nikolai Vadimovich Lukashev},
title = {Synthesis of novel cytotoxic 3-azolylsteroids via Cu-catalyzed C–N coupling},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.025},
number = {3},
pages = {359--361},
doi = {10.1016/j.mencom.2021.04.025}
}
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Parulava, Mikhail Jonovich, et al. “Synthesis of novel cytotoxic 3-azolylsteroids via Cu-catalyzed C–N coupling.” Mendeleev Communications, vol. 31, no. 3, Apr. 2021, pp. 359-361. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.025.

Keywords

antiproliferative activity
copper catalysis
iodoalkenes
MTT assay
nitrogen heterocycles
steroids

Abstract

A series of novel 3-azolylandrosta-3,5-dienes was prepared via Cu-catalyzed Ullmann C–N coupling between a readily available steroidal vinyliodide and a variety of NH-heterocycles. The cytotoxic activity of the target compounds was evaluated against selected cancer cell lines (MCF-7, SKOV-3, DU-145, PC-3). Compound bearing gramine fragment showed the highest antiproliferative effect with IC50 values in the range of 2.0–10.1μm.

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