Oxazolinyl derivatives of [17(20)E]-21-norpregnene differing in the structure of A and B rings. Facile synthesis and inhibition of CYP17A1 catalytic activity
Vladimir A Kostin
1
,
Vladimir A. Zolottsev
1
,
Alexey V Kuzikov
1
,
Rami A Masamrekh
1
,
Victoria Shumyantseva
1
,
А.В. Веселовский
1
,
Sergey V Stulov
1
,
Roman G. Novikov
2, 3
,
Vladimir P Timofeev
2, 3
,
Alexander Yu. Misharin
1
Тип публикации: Journal Article
Дата публикации: 2016-11-01
scimago Q2
wos Q3
БС2
SJR: 0.620
CiteScore: 4.3
Impact factor: 2.3
ISSN: 0039128X, 18785867
PubMed ID:
27505042
Organic Chemistry
Biochemistry
Molecular Biology
Pharmacology
Clinical Biochemistry
Endocrinology
Краткое описание
Five 4,5-dihydro-1,3-oxazole derivatives of [17(20)E]-21-norpregnene, comprising 3β-hydroxy-5-ene (1), 3,6-dioxo-4-ene (2), 3-oxo-4-ene (3), 3α,5α-cyclo-6-oxo (4), 3β-hydroxy-6-oxo (5) fragments were synthesized. Synthesis was conducted with improved procedure, based on reaction of suitably protected [17(20)E]-pregnen-21-oic acids with ethanolamine in presence of triphenyl phosphine, carbon tetrachloride, and triethyl amine. Potency of the compounds 1-5 to inhibit 17α-hydroxylase/17,20-lyase (CYP17A1) activity was studied by highly sensitive electrochemical method, using the enzyme immobilization technique. Compounds 1 and 3 were found to be potent CYP17A1 inhibitors, compounds 2 and 5 were not active, compound 4 strongly and irreversibly suppressed the enzyme activity. Molecular docking of compounds 1-5 in the active site of CYP17A1 showed that positions of all compounds in the enzyme active site were similar.
Найдено
Ничего не найдено, попробуйте изменить настройки фильтра.
Найдено
Ничего не найдено, попробуйте изменить настройки фильтра.
Топ-30
Журналы
|
1
2
3
4
|
|
|
Steroids
4 публикации, 18.18%
|
|
|
Russian Chemical Bulletin
2 публикации, 9.09%
|
|
|
Biomedical Chemistry Research and Methods
2 публикации, 9.09%
|
|
|
Archiv der Pharmazie
1 публикация, 4.55%
|
|
|
Clinical Cancer Drugs
1 публикация, 4.55%
|
|
|
International Journal of Molecular Sciences
1 публикация, 4.55%
|
|
|
Journal of Steroid Biochemistry and Molecular Biology
1 публикация, 4.55%
|
|
|
Computational and Structural Biotechnology Journal
1 публикация, 4.55%
|
|
|
ChemistrySelect
1 публикация, 4.55%
|
|
|
Journal of Inorganic Biochemistry
1 публикация, 4.55%
|
|
|
Biosensors and Bioelectronics
1 публикация, 4.55%
|
|
|
Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry
1 публикация, 4.55%
|
|
|
Biomeditsinskaya Khimiya
1 публикация, 4.55%
|
|
|
Processes
1 публикация, 4.55%
|
|
|
Russian Journal of Oncology
1 публикация, 4.55%
|
|
|
Russian Chemical Reviews
1 публикация, 4.55%
|
|
|
1
2
3
4
|
Издатели
|
1
2
3
4
5
6
7
8
|
|
|
Elsevier
8 публикаций, 36.36%
|
|
|
Wiley
2 публикации, 9.09%
|
|
|
MDPI
2 публикации, 9.09%
|
|
|
Springer Nature
2 публикации, 9.09%
|
|
|
Institute of Biomedical Chemistry
2 публикации, 9.09%
|
|
|
Bentham Science Publishers Ltd.
1 публикация, 4.55%
|
|
|
Pleiades Publishing
1 публикация, 4.55%
|
|
|
Institute of Biochemistry
1 публикация, 4.55%
|
|
|
Cold Spring Harbor Laboratory
1 публикация, 4.55%
|
|
|
Eco-Vector LLC
1 публикация, 4.55%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 публикация, 4.55%
|
|
|
1
2
3
4
5
6
7
8
|
- Мы не учитываем публикации, у которых нет DOI.
- Статистика публикаций обновляется еженедельно.
Вы ученый?
Создайте профиль, чтобы получать персональные рекомендации коллег, конференций и новых статей.
Метрики
22
Всего цитирований:
22
Цитирований c 2024:
2
(9.09%)
Цитировать
ГОСТ |
RIS |
BibTex
Цитировать
ГОСТ
Скопировать
Kostin V. A. et al. Oxazolinyl derivatives of [17(20)E]-21-norpregnene differing in the structure of A and B rings. Facile synthesis and inhibition of CYP17A1 catalytic activity // Steroids. 2016. Vol. 115. pp. 114-122.
ГОСТ со всеми авторами (до 50)
Скопировать
Kostin V. A., Zolottsev V. A., Kuzikov A. V., Masamrekh R. A., Shumyantseva V., Веселовский А., Stulov S. V., Novikov R. G., Timofeev V. P., Misharin A. Y. Oxazolinyl derivatives of [17(20)E]-21-norpregnene differing in the structure of A and B rings. Facile synthesis and inhibition of CYP17A1 catalytic activity // Steroids. 2016. Vol. 115. pp. 114-122.
Цитировать
RIS
Скопировать
TY - JOUR
DO - 10.1016/j.steroids.2016.06.002
UR - https://doi.org/10.1016/j.steroids.2016.06.002
TI - Oxazolinyl derivatives of [17(20)E]-21-norpregnene differing in the structure of A and B rings. Facile synthesis and inhibition of CYP17A1 catalytic activity
T2 - Steroids
AU - Kostin, Vladimir A
AU - Zolottsev, Vladimir A.
AU - Kuzikov, Alexey V
AU - Masamrekh, Rami A
AU - Shumyantseva, Victoria
AU - Веселовский, А.В.
AU - Stulov, Sergey V
AU - Novikov, Roman G.
AU - Timofeev, Vladimir P
AU - Misharin, Alexander Yu.
PY - 2016
DA - 2016/11/01
PB - Elsevier
SP - 114-122
VL - 115
PMID - 27505042
SN - 0039-128X
SN - 1878-5867
ER -
Цитировать
BibTex (до 50 авторов)
Скопировать
@article{2016_Kostin,
author = {Vladimir A Kostin and Vladimir A. Zolottsev and Alexey V Kuzikov and Rami A Masamrekh and Victoria Shumyantseva and А.В. Веселовский and Sergey V Stulov and Roman G. Novikov and Vladimir P Timofeev and Alexander Yu. Misharin},
title = {Oxazolinyl derivatives of [17(20)E]-21-norpregnene differing in the structure of A and B rings. Facile synthesis and inhibition of CYP17A1 catalytic activity},
journal = {Steroids},
year = {2016},
volume = {115},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/j.steroids.2016.06.002},
pages = {114--122},
doi = {10.1016/j.steroids.2016.06.002}
}