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Synthesis of non-steroidal 2-methoxyestradiol mimetics based on the bicyclo[3.3.1]nonane structural motif

Evgeniya Vladimirovna Nurieva 1
Evgeniya Vladimirovna Nurieva
, 
Nikolay Alekseevich Zefirov 1
Nikolay Alekseevich Zefirov
, 
Alexandra Valerievna Mamaeva 1
Alexandra Valerievna Mamaeva
,  , 
Sergei A Kuznetsov 2
Sergei A Kuznetsov
, 
Ol'ga Nikolaevna Zefirova 1, 3
Ol'ga Nikolaevna Zefirova
10.1016/j.mencom.2017.05.007
Published 2017-04-25
Communication , Volume 27, Issue 3, 240-242
7
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Nurieva E. V. et al. Synthesis of non-steroidal 2-methoxyestradiol mimetics based on the bicyclo[3.3.1]nonane structural motif // Mendeleev Communications. 2017. Vol. 27. No. 3. pp. 240-242.
GOST all authors (up to 50) Copy
Nurieva E. V., Zefirov N. A., Mamaeva A. V., Grishin Y. K., Kuznetsov S. A., Zefirova O. N. Synthesis of non-steroidal 2-methoxyestradiol mimetics based on the bicyclo[3.3.1]nonane structural motif // Mendeleev Communications. 2017. Vol. 27. No. 3. pp. 240-242.
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TY - JOUR
DO - 10.1016/j.mencom.2017.05.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.007
TI - Synthesis of non-steroidal 2-methoxyestradiol mimetics based on the bicyclo[3.3.1]nonane structural motif
T2 - Mendeleev Communications
AU - Nurieva, Evgeniya Vladimirovna
AU - Zefirov, Nikolay Alekseevich
AU - Mamaeva, Alexandra Valerievna
AU - Grishin, Yuri Konstantinovich
AU - Kuznetsov, Sergei A
AU - Zefirova, Ol'ga Nikolaevna
PY - 2017
DA - 2017/04/25
PB - Mendeleev Communications
SP - 240-242
IS - 3
VL - 27
ER -
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@article{2017_Nurieva,
author = {Evgeniya Vladimirovna Nurieva and Nikolay Alekseevich Zefirov and Alexandra Valerievna Mamaeva and Yuri Konstantinovich Grishin and Sergei A Kuznetsov and Ol'ga Nikolaevna Zefirova},
title = {Synthesis of non-steroidal 2-methoxyestradiol mimetics based on the bicyclo[3.3.1]nonane structural motif},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.007},
number = {3},
pages = {240--242},
doi = {10.1016/j.mencom.2017.05.007}
}
MLA
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Nurieva, Evgeniya Vladimirovna, et al. “Synthesis of non-steroidal 2-methoxyestradiol mimetics based on the bicyclo[3.3.1]nonane structural motif.” Mendeleev Communications, vol. 27, no. 3, Apr. 2017, pp. 240-242. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.007.

Abstract

Two pairs of bicyclo[3.3.1]nonane derivatives with 2-methoxyphenol moiety were synthesized as non-steroidal 2-methoxyestradiol mimetics demonstrating noticeable cytotoxicity to human lung carcinoma cell line A549. Compounds with 2-methoxyphenol annulated with bicyclo[3.3.1]nonane fragment were obtained using BF3-assisted oxirane opening in 5-(4-benzyloxy-3-methoxyphenyl)-1-oxaspiro[2.5]octanes with simultaneous intramolecular cyclization and reduction as the key step. endo-7-Hydroxybicyclo[3.3.1]nonane-exo-3-carboxylic acid was converted into two esters containing 2-methoxyphenol fragment in either acid or alcohol part of the molecule.

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