Neshat Rozatian
Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids
Rozatian, Neshat; Harsanyi, Antal; Murray, Ben J.; Hampton, Alexander S.; Chin, Emily J.; Cook, Alexander S.; Hodgson, David R.W.; Sandford, Graham
Authors
Antal Harsanyi
Ben J. Murray
Alexander S. Hampton
Emily J. Chin
Alexander S. Cook
Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor
Graham Sandford
Abstract
Fluorinated steroids, which are synthesised by electrophilic fluorination, form a significant proportion of marketed pharmaceuticals. To gain quantitative information on fluorination at the 6‐position of steroids, we conducted kinetics studies on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N−F reagents. We explored the stereoselectivities of fluorination reactions of progesterone enol acetate and the kinetic effects of additives, including methanol and water. The kinetics of epimerisation of 6β‐fluoroprogesterone to the more pharmacologically active 6α‐fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.
Citation
Rozatian, N., Harsanyi, A., Murray, B. J., Hampton, A. S., Chin, E. J., Cook, A. S., Hodgson, D. R., & Sandford, G. (2020). Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids. Chemistry - A European Journal, 26(52), 12027-12035. https://doi.org/10.1002/chem.202001120
Journal Article Type | Article |
---|---|
Acceptance Date | Apr 8, 2020 |
Online Publication Date | Aug 25, 2020 |
Publication Date | 2020-09 |
Deposit Date | Apr 2, 2020 |
Publicly Available Date | Sep 18, 2020 |
Journal | Chemistry - A European Journal |
Print ISSN | 0947-6539 |
Electronic ISSN | 1521-3765 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 26 |
Issue | 52 |
Pages | 12027-12035 |
DOI | https://doi.org/10.1002/chem.202001120 |
Public URL | https://durham-repository.worktribe.com/output/1273551 |
Files
Published Journal Article
(2.4 Mb)
PDF
Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/
Copyright Statement
© 2020 The Authors. Published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
You might also like
Allophycocyanin A is a carbon dioxide receptor in the cyanobacterial phycobilisome
(2022)
Journal Article
Reactivities of electrophilic N–F fluorinating reagents
(2020)
Journal Article
Ubiquitin is a carbon dioxide-binding protein
(2021)
Journal Article
Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides
(2019)
Journal Article
Enolization rates control mono- versus di-fluorination of 1,3-dicarbonyl derivatives
(2019)
Journal Article
Downloadable Citations
About Durham Research Online (DRO)
Administrator e-mail: dro.admin@durham.ac.uk
This application uses the following open-source libraries:
SheetJS Community Edition
Apache License Version 2.0 (http://www.apache.org/licenses/)
PDF.js
Apache License Version 2.0 (http://www.apache.org/licenses/)
Font Awesome
SIL OFL 1.1 (http://scripts.sil.org/OFL)
MIT License (http://opensource.org/licenses/mit-license.html)
CC BY 3.0 ( http://creativecommons.org/licenses/by/3.0/)
Powered by Worktribe © 2024
Advanced Search