Fluorinated Nucleosides: Synthesis, Modulation in Conformation and Therapeutic Application

Advance of structural modification of nucleosides scaffold

(2021) Xia Lin et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Design, Synthesis, and Activity Evaluation of Novel Acyclic Nucleosides as Potential Anticancer Agents In Vitro and In Vivo

(2021) Er-Jun Hao et al.   JOURNAL OF MEDICINAL CHEMISTRY

Antiviral nucleoside analogs

(2021) Vladimir E. Kataev et al.   Chemistry of Heterocyclic Compounds

Synthesis and evaluation of 3′-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents

(2021) Jakob Bouton et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Synthesis of Alkyl Fluorides by Silver‐Catalyzed Radical Decarboxylative Fluorination of Cesium Oxalates

(2021) Émilie Vincent et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Recent Advances in Oligonucleotide Therapeutics in Oncology

(2021) Haoyu Xiong et al.   INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES

Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin

(2021) Alex J. Vendola et al.   ORGANIC LETTERS

Synthesis of phosphonate derivatives of 2′-deoxy-2′-fluorotetradialdose d-nucleosides and tetradialdose d-nucleosides

(2021) Tomáš Lášek et al.   TETRAHEDRON

Enantiomeric 4′-truncated 6′-fluoro-3-deazaneplanocin and its 3-bromo derivative: Synthesis and antiviral properties, including Ebola and Marburg

(2021) Chloe Haverkamp et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Stereoselective Synthesis of (S)- and (N)-Cyclopropyl-Fused Carbocyclic Nucleosides Using Stereoselective Cyclopropanation

(2021) Young Eum Hyun et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis and Structural Characterization of 2′-Deoxy-2′-fluoro-l-uridine Nucleic Acids

(2021) Yuliya Dantsu et al.   ORGANIC LETTERS

C–C Bond Fluorination via Manganese Catalysis

(2021) Yen-Chu Lu et al.   ACS Catalysis

4′-Fluorinated RNA: Synthesis, Structure, and Applications as a Sensitive 19F NMR Probe of RNA Structure and Function

(2020) Qiang Li et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Metabolic and Pharmaceutical Aspects of Fluorinated Compounds

(2020) Benjamin M. Johnson et al.   JOURNAL OF MEDICINAL CHEMISTRY

Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues

(2020) Mieke Guinan et al.   MOLECULES

Contribution of Organofluorine Compounds to Pharmaceuticals

(2020) Munenori Inoue et al.   ACS Omega

Advances in oligonucleotide drug delivery

(2020) Thomas C. Roberts et al.   NATURE REVIEWS DRUG DISCOVERY

Amidate Prodrugs of O-2-Alkylated Pyrimidine Acyclic Nucleosides Display Potent Anti-Herpesvirus Activity

(2020) Min Luo et al.   ACS Medicinal Chemistry Letters

Synthesis and Anti-HCV Activity of Sugar-Modified Guanosine Analogues: Discovery of AL-611 as an HCV NS5B Polymerase Inhibitor for the Treatment of Chronic Hepatitis C

(2020) Guangyi Wang et al.   JOURNAL OF MEDICINAL CHEMISTRY

Unifying the synthesis of nucleoside analogs

(2020) Gavin J. Miller   SCIENCE

Current Contributions of Organofluorine Compounds to the Agrochemical Industry

(2020) Yuta Ogawa et al.   iScience

S-Adenosyl-L-homocysteine hydrolase: Its Inhibitory Activity against Plasmodium falciparum and Development of Malaria Drugs

(2020) Girish Chandra et al.   MINI-REVIEWS IN MEDICINAL CHEMISTRY

Influence of 4′-Substitution on the Activity of Gemcitabine and Its ProTide Against VZV and SARS-CoV-2

(2020) Zihua Zheng et al.   ACS Medicinal Chemistry Letters

Synthesis and Biophysical Characterization of RNAs Containing 2′-Fluorinated Northern Methanocarbacyclic Nucleotides

(2019) Masaaki Akabane-Nakata et al.   ORGANIC LETTERS

Re-Engineering RNA Molecules into Therapeutic Agents

(2019) Martin Egli et al.   ACCOUNTS OF CHEMICAL RESEARCH

Fluorine‐Containing Drugs Approved by the FDA in 2018

(2019) Haibo Mei et al.   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6-(Thiophen-2-yl)-7-fluoro-7-deazapurine

(2019) Vincent Malnuit et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Design, Synthesis, and Anti-RNA Virus Activity of 6′-Fluorinated-Aristeromycin Analogues

(2019) Ji-seong Yoon et al.   JOURNAL OF MEDICINAL CHEMISTRY

Difluorophosphonylated Allylic Ether Moiety as a 2′-Modification of RNA-Type Molecules: Synthesis, Thermal, and Metabolic Studies

(2019) Emmanuel Pfund et al.   ORGANIC LETTERS

Radical Dehydroxymethylative Fluorination of Carbohydrates and Divergent Transformations of the Resulting Reverse Glycosyl Fluorides

(2019) Xin Zhou et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Open-Shell Fluorination of Alkyl Bromides: Unexpected Selectivity in a Silyl Radical-Mediated Chain Process

(2019) Gabrielle H. Lovett et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold

(2018) Katherine L. Seley-Radtke et al.   ANTIVIRAL RESEARCH

Structure-activity relationship of uridine-based nucleoside phosphoramidate prodrugs for inhibition of dengue virus RNA-dependent RNA polymerase

(2018) Gang Wang et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Synthesis of 4′-Thionucleosides as Antitumor and Antiviral Agents

(2018) Yuichi Yoshimura et al.   CHEMICAL & PHARMACEUTICAL BULLETIN

Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and – pyrimidines

(2018) Ji-seong Yoon et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Exploring atypical fluorine-hydrogen bonds and their effects on nucleoside conformations

(2018) Daniel O'Reilly et al.   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis and anti-HIV activity of guanine modified fluorinated acyclic nucleoside phosphonates derivatives

(2018) Min Luo et al.   CHEMISTRY & BIODIVERSITY

Synthesis, Anti-HBV, and Anti-HIV Activities of 3′-Halogenated Bis(hydroxymethyl)-cyclopentenyladenines

(2018) Hiroki Kumamoto et al.   ACS Medicinal Chemistry Letters

Impact of modified ribose sugars on nucleic acid conformation and function

(2017) Marina Evich et al.   HETEROCYCLIC COMMUNICATIONS

Expanding the Antiviral Spectrum of 3-Fluoro-2-(phosphonomethoxy)propyl Acyclic Nucleoside Phosphonates: Diamyl Aspartate Amidate Prodrugs

(2017) Min Luo et al.   JOURNAL OF MEDICINAL CHEMISTRY

Selection of 2′-Fluoro-Modified Aptamers with Optimized Properties

(2017) Deepak Thirunavukarasu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

4′-C-Methoxy-2′-deoxy-2′-fluoro Modified Ribonucleotides Improve Metabolic Stability and Elicit Efficient RNAi-Mediated Gene Silencing

(2017) Elise Malek-Adamian et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Synthesis and biological applications of fluoro-modified nucleic acids

(2017) Fengmin Guo et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Radical fluorination reactions by thermal and photoinduced methods

(2017) Beatriz Lantaño et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Asymmetric Synthesis of (−)-6′-β-Fluoro-aristeromycin via Stereoselective Electrophilic Fluorination

(2017) Gyudong Kim et al.   ORGANIC LETTERS

Synthesis of Antitumor Fluorinated Pyrimidine Nucleosides

(2017) Patrizia Ferraboschi et al.   ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL

Synthesis and anti-proliferative activity of 3′-deoxy-3′-fluoro-3′- C -hydroxymethyl-pyrimidine and purine nucleosides

(2017) Naresh Bhuma et al.   TETRAHEDRON

Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides

(2017) Jakob Bouton et al.   TETRAHEDRON

Synthesis of (R)-Configured 2′-Fluorinated mC, hmC, fC, and caC Phosphoramidites and Oligonucleotides

(2016) Arne S. Schröder et al.   ORGANIC LETTERS

Stereo- and regio-selective synthesis of 3′-C-substituted-(N)-methanocarba adenosines as potential anticancer agents

(2016) Siddhi D. Naik et al.   Organic Chemistry Frontiers

Novel and Efficient Synthesis of gem -Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs)

(2016) Karel Pomeisl et al.   ChemistrySelect

Locked 2′-Deoxy-2′,4′-Difluororibo Modified Nucleic Acids: Thermal Stability, Structural Studies, and siRNA Activity

(2015) Saúl Martínez-Montero et al.   ACS Chemical Biology

4′-Selenonucleosides as Next-Generation Nucleosides

(2015) Pramod K. Sahu et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Recent progress for the synthesis of selected carbocyclic nucleosides

(2015) Maxime Bessières et al.   Future Medicinal Chemistry

Synthesis and Biological Evaluation of 4-Substituted Fluoronucleoside Analogs for the Treatment of Hepatitis B Virus Infection

(2015) Qinghua Yang et al.   JOURNAL OF MEDICINAL CHEMISTRY

Structure–Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities

(2015) Girish Chandra et al.   JOURNAL OF MEDICINAL CHEMISTRY

Applications of Fluorine in Medicinal Chemistry

(2015) Eric P. Gillis et al.   JOURNAL OF MEDICINAL CHEMISTRY

Investigation and Conformational Analysis of Fluorinated Nucleoside Antibiotics Targeting Siderophore Biosynthesis

(2015) Surendra Dawadi et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis and Properties of 2′-Deoxy-2′,4′-difluoroarabinose-Modified Nucleic Acids

(2015) Saúl Martínez-Montero et al.   JOURNAL OF ORGANIC CHEMISTRY

Regio- and stereoselective synthesis of 2′-β-substituted-fluoroneplanocin A analogues as potential anticancer agents

(2015) Akshata Nayak et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Synthesis and Duplex-Stabilizing Properties of FluorinatedN-Methanocarbathymidine Analogues Locked in the C3′-endoConformation

(2014) Michael E. Jung et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

The synthesis of gemcitabine

(2014) Kylie Brown et al.   CARBOHYDRATE RESEARCH

Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C–F Bond Activation To Access Fluorinated Building Blocks

(2014) Theresia Ahrens et al.   CHEMICAL REVIEWS

Stereoselective Synthesis of 2′-Fluoro-6′-methylene Carbocyclic Adenosine via Vince Lactam

(2014) Uma S. Singh et al.   JOURNAL OF ORGANIC CHEMISTRY

Rigid 2′,4′-Difluororibonucleosides: Synthesis, Conformational Analysis, and Incorporation into Nascent RNA by HCV Polymerase

(2014) Saúl Martínez-Montero et al.   JOURNAL OF ORGANIC CHEMISTRY

Comparison of Duplex Stabilizing Properties of 2′-Fluorinated Nucleic Acid Analogues with Furanose and Non-Furanose Sugar Rings

(2014) Michael E. Østergaard et al.   JOURNAL OF ORGANIC CHEMISTRY

A review of methods to synthesise 4′-substituted nucleosides

(2014) Mark Betson et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

The development for the synthesis of chiral acyclic nucleosides and their phosphonates

(2014) Ming-Sheng Xie et al.   TETRAHEDRON LETTERS

Dancing with chemical formulae of antivirals: A personal account

(2013) Erik De Clercq   BIOCHEMICAL PHARMACOLOGY

Advances in the enantioselective synthesis of carbocyclic nucleosides

(2013) Omar Boutureira et al.   CHEMICAL SOCIETY REVIEWS

Influence of 2′-Fluoro versus 2′-O-Methyl Substituent on the Sugar Puckering of 4′-C-Aminomethyluridine

(2013) Kiran R. Gore et al.   JOURNAL OF ORGANIC CHEMISTRY

Medicinal Chemistry of Fluorinated Cyclic and Acyclic Nucleoside Phosphonates

(2013) Ondřej Baszczyňski et al.   MEDICINAL RESEARCH REVIEWS

2′-Fluoro RNA Shows Increased Watson-Crick H-Bonding Strength and Stacking Relative to RNA: Evidence from NMR and Thermodynamic Data

(2012) Amritraj Patra et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

2′-Fluoro-6′-methylene-carbocyclic adenosine phosphoramidate (FMCAP) prodrug: In vitro anti-HBV activity against the lamivudine–entecavir resistant triple mutant and its mechanism of action

(2012) Ravindra K. Rawal et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Synthesis, Duplex Stabilization and Structural Properties of a Fluorinated Carbocyclic LNA Analogue

(2012) Punit P. Seth et al.   CHEMBIOCHEM

Conformational Analysis of Furanoside-Containing Mono- and Oligosaccharides

(2012) Hashem A. Taha et al.   CHEMICAL REVIEWS

Designing Chemically Modified Oligonucleotides for Targeted Gene Silencing

(2012) Glen F. Deleavey et al.   CHEMISTRY & BIOLOGY

Synthesis and applications of fluorinated nucleoside analogues

(2012) Hanna Wójtowicz-Rajchel   JOURNAL OF FLUORINE CHEMISTRY

Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity

(2012) Won Jun Choi et al.   JOURNAL OF MEDICINAL CHEMISTRY

Organic Chemist Whose Inventions Reshaped the Antiviral Drug World

(2012) Erik De Clercq   MEDICINAL RESEARCH REVIEWS

Stereoselective Synthesis of Fluoro-homoneplanocin A as a Potential Antiviral Agent

(2012) Girish Chandra et al.   ORGANIC LETTERS

Unique Gene-Silencing and Structural Properties of 2′-Fluoro-Modified siRNAs

(2011) Muthiah Manoharan et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Antiviral activity of novel 2′-fluoro-6′-methylene-carbocyclic adenosine against wild-type and drug-resistant hepatitis B virus mutants

(2011) Jianing Wang et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Synthesis and Structural Characterization of 2′-Fluoro-α-L-RNA-Modified Oligonucleotides

(2011) Troels Bundgaard Jensen et al.   CHEMBIOCHEM

Synthesis of new 2′-deoxy-2′-fluoro-4′-azido nucleoside analogues as potent anti-HIV agents

(2011) Qiang Wang et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Synthesis, Improved Antisense Activity and Structural Rationale for the Divergent RNA Affinities of 3′-Fluoro Hexitol Nucleic Acid (FHNA and Ara-FHNA) Modified Oligonucleotides

(2011) Martin Egli et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Locked and Unlocked Nucleosides in Functional Nucleic Acids

(2011) Holger Doessing et al.   MOLECULES

Regio- and stereoselective synthesis of truncated 3′-aminocarbanucleosides and their binding affinity at the A3 adenosine receptor

(2011) Mun Ju Choi et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Synthesis and anti-HIV activity of 2′-deoxy-2′-fluoro-4′-C-ethynyl nucleoside analogs

(2010) Qiang Wang et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Synthesis of Bicyclonucleosides Having a C−C Bridge†

(2010) Jacques Lebreton et al.   CHEMICAL REVIEWS

Energetically Important C−H···F−C Pseudohydrogen Bonding in Water: Evidence and Application to Rational Design of Oligonucleotides with High Binding Affinity

(2010) Maryam Yahyaee Anzahaee et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Unexpected origins of the enhanced pairing affinity of 2′-fluoro-modified RNA

(2010) Pradeep S. Pallan et al.   NUCLEIC ACIDS RESEARCH

Differential stability of 2′F-ANA•RNA and ANA•RNA hybrid duplexes: roles of structure, pseudohydrogen bonding, hydration, ion uptake and flexibility

(2010) Jonathan K. Watts et al.   NUCLEIC ACIDS RESEARCH

A New DNA Building Block, 4′-Selenothymidine: Synthesis and Modification to 4′-Seleno-AZT as a Potential Anti-HIV Agent

(2010) Varughese Alexander et al.   ORGANIC LETTERS

C-Nucleosides: Synthetic Strategies and Biological Applications

(2009) Michal Hocek   CHEMICAL REVIEWS

North- and South-Bicyclo[3.1.0]Hexene Nucleosides: The Effect of Ring Planarity on Anti-HIV Activity

(2009) Pamela L. Russ et al.   ChemMedChem

Fluorine in medicinal chemistry: a century of progress and a 60-year retrospective of selected highlights

(2009) Robert Filler et al.   Future Medicinal Chemistry

Recent advances in the synthesis of fluorinated nucleosides

(2009) Xiao-Long Qiu et al.   TETRAHEDRON

Recent Approaches in the Synthesis of Conformationally Restricted Nucleoside Analogues

(2008) Christophe Mathé et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Potent inhibition of microRNA in vivo without degradation

(2008) Scott Davis et al.   NUCLEIC ACIDS RESEARCH

Understanding organofluorine chemistry. An introduction to the C–F bond

(2007) David O'Hagan   CHEMICAL SOCIETY REVIEWS

Fluorine in medicinal chemistry

(2007) Sophie Purser et al.   CHEMICAL SOCIETY REVIEWS

First Synthesis of 4‘-Selenonucleosides Showing Unusual Southern Conformation

(2007) Lak Shin Jeong et al.   ORGANIC LETTERS