Recent advances in the synthesis of fluorinated nucleosides

Qiu, Xiao‐Long; Xu, Xiu‐Hua; Qing, Feng‐Ling

doi:10.1016/j.tet.2009.11.001

Cited by 144 publications

(42 citation statements)

References 374 publications

(288 reference statements)

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“…Дальнейший прогресс в этом направлении исследований связан с синтезом новых фторированных нуклеозидов, а также более глубоком понимании механизмов их действия. [6,9,11,13].…”

Section: результаты и их обсуждениеunclassified

Study of Antiadenoviralactivity of New Fluorinecontaining Heterocyclic Compounds

Biliavska¹,

Повниця²,

Шермолович³

et al. 2014

Microbiology&Biotechnology

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Section: результаты и их обсуждениеunclassified

Study of Antiadenoviralactivity of New Fluorinecontaining Heterocyclic Compounds

Biliavska¹,

Повниця²,

Шермолович³

et al. 2014

Microbiology&Biotechnology

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“…Asymmetrical bromonium salts [R F (R F 0 )Br]Y, where R F is a perfluorinated aryl, alkenyl, and alkynyl group and Y a weakly coordinating anion, have now been prepared. 59 In closely related work symmetrical bromonium salts [(R F ) 2 Br]Y (R F = aryl, alkenyl, and alkynyl) have also been prepared. 60 An intriguing side note to this paper is the inclusion of new data regarding the exact nature of BF 3 in CH 3 CN and CH 2 Cl 2 including 19 F and 11 B NMR studies.…”

Section: Hypervalent Halogen Compoundsmentioning

confidence: 99%

Halogens

Justik

2011

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This chapter reports on the literature published during 2010 concerning the elemental halogens and compounds containing these elements in their positive oxidation states. Its intent is to highlight discovery and provide insight into current research trends. HighlightsHighlights of the 2010 literature concerning the halogens include the preparation of the first examples of dialkyl chloronium ions, 15 a new class of electrophilic halogen sources 18 and continued vibrancy in hypervalent bromine chemistry. [56][57][58][59][60] Elemental halogens Fully 30% of the top pharmaceuticals in sale contain a fluorine atom as highlighted by a recent review. 1 Furthermore, the innate nuclear properties of 18 F as a radiotracer for positron emission tomography (PET) and 19 F as an active nucleus for magnetic resonance imaging (MRI) fosters development of methodology for the selective fluorination of biomolecules. One recent review outlines the synthesis of fluorinated nucleosides toward their use as probes for the study of biomolecular pathways. 2 It has been noted that there is an apparent monotony of structural motifs by which fluorine is incorporated into biomolecules. To address this, a greater understanding of ''emergent'' fluorinated groups such as a-fluorinated ethers, thioethers, amines and phosphines has been suggested. 3 Furthermore, the stereoselective introduction of fluorine atoms can be exploited as a conformational tool for the synthesis of shape-controlled biomolecules. 4 The use of N-F electrophilic fluorination reagents such as Selectfluor s (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis-(tetrafluoroborate)) and NFSI (N-fluorobenzenesulfonimide) continues to receive the majority of focus in organic synthesis. A versatile one-pot method for converting aromatic and heteroaromatic halides by halide-Mg exchange and electrophilic fluorination of organomagnesium reagents with NFSI has now been developed which can even be applied to sterically congested substrates. 5 A potentially new role for fluorine in

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“…1-3 Prominent examples of C2' fluorinated nucleosides with potent biological activities include anticancer drugs gemcitabine, 4-6 and clofarabine; 7,8 and hepatitis C virus drug sofosbuvir. 9,10 In the last 40 years, numerous methods for the incorporation of fluorine atoms into organic molecules have been developed, as summarized in excellent reviews.…”

Section: Introductionmentioning

confidence: 99%

Studies toward the oxidative and reductive activation of C–S bonds in 2′-S-aryl-2ʹ-thiouridine derivatives

et al. 2016

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Studies directed toward the oxidative and reductive desulfurization of readily available 2'-S-aryl-2'-thiouridine derivatives were investigated with the prospect to functionalize the C2'-position of nucleosides. The oxidative desulfurization-difluorination strategy was successful on 2-(arylthio)alkanoate surrogates, while extension of the combination of oxidants and fluoride sources was not an efficient fluorination protocol when applied to 2'-S-aryl-2'-thiouridine derivatives, resulting mainly in C5-halogenation of the pyrimidine ring and C2'-monofluorination without desulfurization. Cyclic voltammetry of 2'-arylsulfonyl-2'-deoxyuridines and their 2'-fluorinated analogues showed that cleavage of the arylsulfone moiety could occur, although at relatively high cathodic potentials. While reductive-desulfonylation of 2'-arylsulfonyl-2'-deoxyuridines with organic electron donors (OEDs) gave predominantly base-induced furan type products, chemical (OED) and electrochemical reductive-desulfonylation of the α-fluorosulfone derivatives yielded the 2'-deoxy-2'-fluorouridine and 2',3'-didehydro-2',3'-dideoxy-2'-fluorouridine derivatives. These results provided good evidence of the generation of a C2'-anion through carbon-sulfur bond cleavage, opening new horizons for the reductive-functionalization approaches in nucleosides.

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Recent advances in the synthesis of fluorinated nucleosides

Cited by 144 publications

References 374 publications

Study of Antiadenoviralactivity of New Fluorinecontaining Heterocyclic Compounds

Study of Antiadenoviralactivity of New Fluorinecontaining Heterocyclic Compounds

Halogens

Studies toward the oxidative and reductive activation of C–S bonds in 2′-S-aryl-2ʹ-thiouridine derivatives

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