Steroids—CXXI synthesis of halogenated steroid hormones

Bowers, A.; Denot, E.; Sánchez, María Blanca; Ringold, Howard J.

doi:10.1016/0040-4020(59)80062-4

Cited by 24 publications

(12 citation statements)

References 32 publications

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“…Wie aus Tabelle 13 hervorgeht, ist 33 b mehr als zehnmal wirksamer als natürliches Hydrocortison – weit wichtiger aber war, dass diese Studien die Fluorierung als eine vielversprechende Methode zur Verbesserung der Aktivität pharmakologisch relevanter Verbindungen etablierten. Beispiele für Glucocorticoide mit dazugehörigen Aktivitäten finden sich in Abbildung 4 99. Wie bereits erwähnt, fanden Herrinton et al, dass 1 ein hoch effizientes Fluorierungsmittel zur Synthese von 8 ist 26…”

Section: Verschiedene Anwendungen Fluorierter Verbindungenunclassified

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Selectfluor: Mechanismen und Anwendungen

et al. 2004

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Der Ersatz von Wasserstoff durch Fluor in organischen Substraten ist wegen der hohen Elektronegativität des Fluors bei fast gleich bleibendem Raumanspruch von großem Interesse in der Synthesechemie. Viele Quellen für nucleophiles Fluor zur Derivatisierung unter sauren, basischen und neutralen Bedingungen stehen zur Verfügung. Hingegen erforderte eine elektrophile Fluorierung früher den Einsatz von molekularem Fluor, was aufgrund dessen Toxizität und Explosionsneigung zu einer nur begrenzten Anwendung dieser Methode geführt hat. Der Bedarf an einem elektrophilen Fluorierungsreagens, das sicher zu handhaben, stabil und hoch reaktiv ist und in der industriellen Produktion als Alternative zum hoch giftigen gasförmigen Fluor eingesetzt werden kann, führte letztlich zur Entwicklung von Selectfluor (1). Dieses Reagens ist eines der reaktivsten elektrophilen Fluorierungsmittel und dazu noch ungefährlich, nicht toxisch und leicht zu handhaben. In diesem Aufsatz beschreiben wir die zahlreichen Einsatzmöglichkeiten von Selectfluor und diskutieren mögliche Reaktionsmechanismen.

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Section: Verschiedene Anwendungen Fluorierter Verbindungenunclassified

“… Biologische Aktivitäten von Fluorcorticoiden;99 jeweils angegeben ist die entzündungshemmende Aktivität in der Ratte bezogen auf Hydrocortisonacetat. …”

Section: Verschiedene Anwendungen Fluorierter Verbindungenunclassified

Selectfluor: Mechanismen und Anwendungen

et al. 2004

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“…The methods for synthesizing steroids have focused on key transformations, including alteration of the configuration of a stereocenter, aromatization of a ring, incorporation of a heteroatom and annulation of a heterocyclic ring. By making structural modifications, the physiological activity of a compound can be changed [11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure, Hirshfeld surfaces, and thermal, mechanical and dielectrical properties of cholest-5-ene

Shamsuzzaman

Khanam

Mashrai

et al. 2017

Journal of Taibah University for Science

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The title compound derived from 3β-chlorocholest-5-ene has been synthesized and characterized successfully. A single crystal X-ray investigation of the compound revealed that the van der Waals interactions play a key role in the formation of the elementary structure. Hirshfeld surface analysis was used to visualize the fidelity of the crystal structure. This method permitted the identification of individual types of intermolecular contacts and their impact on crystal packing. Molecules are linked by a combination of C H• • •H and C• • •H contacts, which have clear signatures in the fingerprint plots. The absorption spectrum exhibited a strong absorption band of approximately 246 nm, and the fluorescence spectrum of the compound showed one broad peak at 367 nm. Thermal studies established that the compound undergoes no phase transition and is stable up to 200 • C. The hardness of the grown crystal increases as the load increases. The electric permittivity of cholest-5-ene decreases with increasing frequency and becomes almost constant at high frequencies.

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“…Several examples of fluorinated glucocorticoids and their corresponding activities can be found in Figure 4. [99] As stated previously, Herrinton and co-workers determined that 1 is a highly efficient fluorinating reagent for the synthesis of 8.…”

Section: Fluorinated Glucocorticoidsmentioning

confidence: 99%

“…The good inhibition observed with the anomerically nonnatural 13a indicates that the binding Figure 4. Biological activities of fluorocorticoids; [99] in each case the anti-inflammatory activity in rats relative to hydrocortisone acetate is given. [52,101] GDP-Fuc Table 15: Inhibition of a sialyl-and two galactosyltransferases.…”

Section: Fluorinated Glycosyltransferase Inhibitorsmentioning

confidence: 99%

Selectfluor: Mechanistic Insight and Applications

et al. 2004

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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.

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Steroids—CXXI synthesis of halogenated steroid hormones

Cited by 24 publications

References 32 publications

Selectfluor: Mechanismen und Anwendungen

Selectfluor: Mechanismen und Anwendungen

Synthesis, crystal structure, Hirshfeld surfaces, and thermal, mechanical and dielectrical properties of cholest-5-ene

Selectfluor: Mechanistic Insight and Applications

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