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Tytuł pozycji:

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.

Tytuł :
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.
Autorzy :
Kostin VA; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
Zolottsev VA; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
Kuzikov AV; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
Masamrekh RA; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
Shumyantseva VV; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
Veselovsky AV; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
Stulov SV; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
Novikov RA; Engelhardt Institute of Molecular Biology RAS, Moscow, Russia.
Timofeev VP; Engelhardt Institute of Molecular Biology RAS, Moscow, Russia. Electronic address: .
Misharin AY; Orekhovich Institute of Biomedical Chemistry, Moscow, Russia.
Pokaż więcej
Źródło :
Steroids [Steroids] 2016 Nov; Vol. 115, pp. 114-122. Date of Electronic Publication: 2016 Aug 06.
Typ publikacji :
Journal Article; Research Support, Non-U.S. Gov't
Język :
English
Imprint Name(s) :
Publication: New York Ny : Elsevier
Original Publication: San Francisco.
MeSH Terms :
Enzyme Inhibitors/*chemistry
Enzyme Inhibitors/*pharmacology
Oxazoles/*chemistry
Steroid 17-alpha-Hydroxylase/*antagonists & inhibitors
Steroid 17-alpha-Hydroxylase/*metabolism
Humans ; Molecular Docking Simulation ; Molecular Structure ; Structure-Activity Relationship
Contributed Indexing :
Keywords: CYP17A1 inhibitors*; Electrochemistry*; Molecular modeling*; Oxazolinyl derivatives of [17(20)E]-21-norpregnene*; Structure-activity relationships*; Synthesis*
Substance Nomenclature :
0 (Enzyme Inhibitors)
0 (Oxazoles)
EC 1.14.14.19 (CYP17A1 protein, human)
EC 1.14.14.19 (Steroid 17-alpha-Hydroxylase)
Entry Date(s) :
Date Created: 20160810 Date Completed: 20170830 Latest Revision: 20171218
Update Code :
20201218
DOI :
10.1016/j.steroids.2016.06.002
PMID :
27505042
Czasopismo naukowe
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.
(Copyright © 2016. Published by Elsevier Inc.)

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