Fluorinated steroids and their derivatives

Jasem, Yosef Al; Thiemann, Thies; Gano, Lurdes; Oliveira, Maria Cristina

doi:10.1016/j.jfluchem.2016.03.009

Cited by 19 publications

(22 citation statements)

References 191 publications

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“…[1] Since this observation, numerous fluorinated steroids have been marketedf or the treatment of various disease classes, including cancers and inflammation. [2] In particular, fluorosteroids bearingaf luorine atom at the 6-position, such as flurandrenolide 2 and fluticasone 3,continue to be commercially significant (Figure1). Fluticasone therapeutics were ranked in the top 200 drugs prescribed in the USA in 2017.…”

Section: Introductionmentioning

confidence: 99%

Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids

Rozatian

Harsányi

Murray

et al. 2020

Chemistry A European J

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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, kinetics studies were conducted on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N−F reagents. The stereoselectivities of fluorination reactions of progesterone enol acetate and the kinetic effects of additives, including methanol and water, were investigated. The kinetics of epimerisation of 6β‐fluoroprogesterone to the more pharmacologically active 6α‐fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.

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Section: Introductionmentioning

confidence: 99%

Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids

Rozatian

Harsányi

Murray

et al. 2020

Chemistry A European J

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“…To evaluate the ability to extend our strategy to aromatic steroids, the protected 4‐methylphenol model substrate 7 was submitted to the optimized reaction conditions and led to the exclusive formation of 8 in 64 % yield. Our method was therefore next extended to the protected estrone 9 to generate its SCF 3 analogue 10 in 64 % yield . Contrary to literature precedents, trifluoromethylthiolation at the nonclassical position is observed because of the ester protonation under the HF/SbF 5 conditions …”

Section: Methodsmentioning

confidence: 88%

Superacid‐Catalyzed Trifluoromethylthiolation of Aromatic Amines

et al. 2016

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“…30 Studying the fluorination of naturally occurring steroids can lead to new innovations in hormone medicine as well as discovering new methods of fluorinating these polycyclic lipids. Estrone 64, one of several naturally occurring estrogens, is a hormone secreted from the ovaries.…”

Section: Steroidsmentioning

confidence: 99%

Selective fluorination of natural products

Luzzio¹,

Monsen²,

Zhdankin³

2017

Arkivoc

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Compounds derived from natural sources including animals, plants, and micro-organisms have been widely used for pharmaceuticals, materials, and agrochemicals. The use of these natural products has grown increasingly over the years and the demand for more improved, biologically active, and safer derivatives of natural products has been investigated by many researchers in the areas of synthetic and medicinal chemistry. Due to the unique characteristics of fluorinated compounds, and the increased or more favorable biological activity which usually accompanies fluorinated analogues of medicinally-important compounds, the fluorination of natural products has gained much attention. This review aims at exploring the range of specific natural product types that have been selectively fluorinated as well as how fluorination was expected to affect their biological activities and physiochemical properties.

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Fluorinated steroids and their derivatives

Cited by 19 publications

References 191 publications

Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids

Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids

Superacid‐Catalyzed Trifluoromethylthiolation of Aromatic Amines

Selective fluorination of natural products

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