9α-Fluoro DERIVATIVES OF CORTISONE AND HYDROCORTISONE

Fried, Josef; Sabo, Emily F.

doi:10.1021/ja01634a101

Cited by 315 publications

(142 citation statements)

References 0 publications

Supporting

Mentioning

137

Contrasting

Unclassified

Order By: Relevance

“…1 This discovery gave added impetus to the development of methodology for the introduction of fluorine atoms into organic systems and, today, around 20% of commercially significant pharmaceuticals and 30 % of all agrochemicals contain fluorinated groups within their structures that perform a variety of functions such as increasing metabolic stability, increasing lipophilicity and bioavailability. As the pharmaceutical industry seeks to further develop new pharmaceuticals that have more threedimensional structure in design strategies that are moving away from aromatic 'flatland', 6 methodology for the incorporation of fluorine atoms located at sp 3 centres is gaining in importance.…”

Section: Introductionmentioning

confidence: 99%

2-Fluoromalonate Esters: Fluoroaliphatic Building Blocks for the Life Sciences

Harsányi

Sandford

2014

Org. Process Res. Dev.

View full text Add to dashboard Cite

Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details.

show abstract

Section: Introductionmentioning

confidence: 99%

2-Fluoromalonate Esters: Fluoroaliphatic Building Blocks for the Life Sciences

Harsányi

Sandford

2014

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…The first reported use of fluorination to enhance the activity of a medicinally useful compound was by Fried and Sabo in 1954. [97] A year earlier, they had described the synthesis of derivatives of the glucocorticoid hydrocortisone (33 a), a steroid hormone with anti-inflammatory and thymolytic activity.…”

Section: Fluorinated Glucocorticoidsmentioning

confidence: 99%

Selectfluor: Mechanistic Insight and Applications

et al. 2004

View full text Add to dashboard Cite

The replacement of hydrogen atoms with fluorine substituents in organic substrates is of great interest in synthetic chemistry because of the strong electronegativity of fluorine and relatively small steric footprint of fluorine atoms. Many sources of nucleophilic fluorine are available for the derivatization of organic molecules under acidic, basic, and neutral conditions. However, electrophilic fluorination has historically required molecular fluorine, whose notorious toxicity and explosive tendencies limit its application in research. The necessity for an electrophilic fluorination reagent that is safe, stable, highly reactive, and amenable to industrial production as an alternative to very hazardous molecular fluorine was the inspiration for the discovery of selectfluor. This reagent is not only one of the most reactive electrophilic fluorinating reagents available, but it is also safe, nontoxic, and easy to handle. In this Review we document the many applications of selectfluor and discuss possible mechanistic pathways for its reaction.

show abstract

Section: B Metallochlorinsmentioning

confidence: 99%

“…151 The equilibrium between five and six coordination is temperature dependent. 151 Katz et al 152 derived from X H nmr data equilibrium constants for the formation of the monosolvate of chlorophyll a with alcohols, which are about 100 times larger than for the disolvate. The preferential five coordination of chlorophylls is also manifested in chlorophyll aggregates, which arise from ligation of the central Mg of one molecule, preferentially with the peripheral 9-carbonyl group in another molecule 3,148 (for details, see Volume V, Chapter 9).…”

Section: B Metallochlorinsmentioning

confidence: 99%