Steroids, volume 77, issue 12, pages 1233-1241
Neuroactive steroids with perfluorobenzoyl group
Ivan Černý
1
,
Milos Budesinsky
1
,
Vladimir Pouzar
1
,
Vojtech Vyklicky
2, 3
,
Barbora Krausova
3
,
L. Vyklický
3
1
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i.,166 10 Prague 6, Czech Republic.
|
3
Institute of Physiology, Academy of Sciences of the Czech Republic, v.v.i., 142 20 Prague, Czech Republic
|
Publication type: Journal Article
Publication date: 2012-10-01
Organic Chemistry
Biochemistry
Molecular Biology
Pharmacology
Clinical Biochemistry
Endocrinology
Abstract
During an initial study in searching for the alternative derivatives suitable for photolabeling of neuroactive steroids, perfluorobenzoates and perfluorobenzamides in position 17 of 5β-androstan-3α-ol were synthesized from the corresponding 17-hydroxy and 17-amino derivatives. After transformation into glutamates or sulfates, 17α-epimers had comparable inhibitory activity at NMDA receptors to the natural neurosteroid (20-oxo-5β-pregnan-3β-yl sulfate), however, were more potent (2- to 36-fold) than their 17β-substituted analogs. In one case, fluorine in position 4' of perfluorobenzoate group was substituted with azide and activity of the final glutamate was retained comparing with the corresponding perfluorobenzoate. The series was expanded with perfluorobenzoyl derivatives of pregnanolone: Perfluorobenzamide of glutamate and perfluorobenzoate of 11α-hydroxy pregnanolone were prepared and tested. From nine tested compounds, four of them exhibit very good inhibition activity and can serve as promising leads for photolabeling experiments.
Top-30
Citations by journals
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1 publication, 25%
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Scientific Reports
1 publication, 25%
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Microchemical Journal
1 publication, 25%
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Russian Chemical Reviews
1 publication, 25%
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Citations by publishers
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1 publication, 25%
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Springer Nature
1 publication, 25%
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Elsevier
1 publication, 25%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 25%
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Černý I. et al. Neuroactive steroids with perfluorobenzoyl group // Steroids. 2012. Vol. 77. No. 12. pp. 1233-1241.
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Černý I., Budesinsky M., Pouzar V., Vyklicky V., Krausova B., Vyklický L. Neuroactive steroids with perfluorobenzoyl group // Steroids. 2012. Vol. 77. No. 12. pp. 1233-1241.
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TY - JOUR
DO - 10.1016/j.steroids.2012.07.004
UR - https://doi.org/10.1016/j.steroids.2012.07.004
TI - Neuroactive steroids with perfluorobenzoyl group
T2 - Steroids
AU - Černý, Ivan
AU - Budesinsky, Milos
AU - Pouzar, Vladimir
AU - Vyklicky, Vojtech
AU - Krausova, Barbora
AU - Vyklický, L.
PY - 2012
DA - 2012/10/01 00:00:00
PB - Elsevier
SP - 1233-1241
IS - 12
VL - 77
SN - 0039-128X
SN - 1878-5867
ER -
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@article{2012_Černý,
author = {Ivan Černý and Milos Budesinsky and Vladimir Pouzar and Vojtech Vyklicky and Barbora Krausova and L. Vyklický},
title = {Neuroactive steroids with perfluorobenzoyl group},
journal = {Steroids},
year = {2012},
volume = {77},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/j.steroids.2012.07.004},
number = {12},
pages = {1233--1241},
doi = {10.1016/j.steroids.2012.07.004}
}
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MLA
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Černý, Ivan, et al. “Neuroactive steroids with perfluorobenzoyl group.” Steroids, vol. 77, no. 12, Oct. 2012, pp. 1233-1241. https://doi.org/10.1016/j.steroids.2012.07.004.