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
Publication type: Journal Article
Publication date: 2016-11-01
scimago Q2
wos Q3
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
Abstract
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.
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GOST
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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.
GOST all authors (up to 50)
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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.
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RIS
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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 -
Cite this
BibTex (up to 50 authors)
Copy
@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}
}